AU594760B2 - Process for making azo pigments - Google Patents
Process for making azo pigments Download PDFInfo
- Publication number
- AU594760B2 AU594760B2 AU72407/87A AU7240787A AU594760B2 AU 594760 B2 AU594760 B2 AU 594760B2 AU 72407/87 A AU72407/87 A AU 72407/87A AU 7240787 A AU7240787 A AU 7240787A AU 594760 B2 AU594760 B2 AU 594760B2
- Authority
- AU
- Australia
- Prior art keywords
- acid
- reaction
- coupling component
- coupling
- reaction step
- Prior art date
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- 239000000049 pigment Substances 0.000 title claims description 20
- 238000000034 method Methods 0.000 title claims description 13
- 230000008878 coupling Effects 0.000 claims description 41
- 238000010168 coupling process Methods 0.000 claims description 41
- 238000005859 coupling reaction Methods 0.000 claims description 41
- 238000006243 chemical reaction Methods 0.000 claims description 34
- 239000000243 solution Substances 0.000 claims description 25
- 239000002253 acid Substances 0.000 claims description 16
- 238000002156 mixing Methods 0.000 claims description 16
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 claims description 12
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 9
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 8
- 239000000725 suspension Substances 0.000 claims description 7
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims description 6
- 238000006149 azo coupling reaction Methods 0.000 claims description 6
- 239000007864 aqueous solution Substances 0.000 claims description 5
- 239000002245 particle Substances 0.000 claims description 5
- KJCVRFUGPWSIIH-UHFFFAOYSA-N 1-naphthol Chemical group C1=CC=C2C(O)=CC=CC2=C1 KJCVRFUGPWSIIH-UHFFFAOYSA-N 0.000 claims description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 4
- 239000006172 buffering agent Substances 0.000 claims description 4
- 230000007935 neutral effect Effects 0.000 claims description 4
- 239000012670 alkaline solution Substances 0.000 claims description 3
- 229910000147 aluminium phosphate Inorganic materials 0.000 claims description 3
- 239000000203 mixture Substances 0.000 claims description 3
- ISWSIDIOOBJBQZ-UHFFFAOYSA-M phenolate Chemical compound [O-]C1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-M 0.000 claims description 3
- 229940031826 phenolate Drugs 0.000 claims description 3
- 230000001376 precipitating effect Effects 0.000 claims description 3
- 239000000126 substance Substances 0.000 claims description 3
- KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 claims description 2
- 239000004327 boric acid Substances 0.000 claims description 2
- 239000003643 water by type Substances 0.000 claims description 2
- 239000012954 diazonium Substances 0.000 description 14
- 239000000463 material Substances 0.000 description 13
- 150000001989 diazonium salts Chemical class 0.000 description 11
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 239000000047 product Substances 0.000 description 5
- 239000012071 phase Substances 0.000 description 4
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-O diazynium Chemical compound [NH+]#N IJGRMHOSHXDMSA-UHFFFAOYSA-O 0.000 description 3
- IIACRCGMVDHOTQ-UHFFFAOYSA-N sulfamic acid Chemical compound NS(O)(=O)=O IIACRCGMVDHOTQ-UHFFFAOYSA-N 0.000 description 3
- GVBHRNIWBGTNQA-UHFFFAOYSA-N 2-methoxy-4-nitroaniline Chemical compound COC1=CC([N+]([O-])=O)=CC=C1N GVBHRNIWBGTNQA-UHFFFAOYSA-N 0.000 description 2
- DLURHXYXQYMPLT-UHFFFAOYSA-N 2-nitro-p-toluidine Chemical compound CC1=CC=C(N)C([N+]([O-])=O)=C1 DLURHXYXQYMPLT-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
- IOVCWXUNBOPUCH-UHFFFAOYSA-M Nitrite anion Chemical compound [O-]N=O IOVCWXUNBOPUCH-UHFFFAOYSA-M 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 239000008395 clarifying agent Substances 0.000 description 2
- 150000008049 diazo compounds Chemical class 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 235000010288 sodium nitrite Nutrition 0.000 description 2
- AVYGCQXNNJPXSS-UHFFFAOYSA-N 2,5-dichloroaniline Chemical compound NC1=CC(Cl)=CC=C1Cl AVYGCQXNNJPXSS-UHFFFAOYSA-N 0.000 description 1
- LOCWBQIWHWIRGN-UHFFFAOYSA-N 2-chloro-4-nitroaniline Chemical compound NC1=CC=C([N+]([O-])=O)C=C1Cl LOCWBQIWHWIRGN-UHFFFAOYSA-N 0.000 description 1
- JWAZRIHNYRIHIV-UHFFFAOYSA-N 2-naphthol Chemical compound C1=CC=CC2=CC(O)=CC=C21 JWAZRIHNYRIHIV-UHFFFAOYSA-N 0.000 description 1
- JFGQHAHJWJBOPD-UHFFFAOYSA-N 3-hydroxy-n-phenylnaphthalene-2-carboxamide Chemical compound OC1=CC2=CC=CC=C2C=C1C(=O)NC1=CC=CC=C1 JFGQHAHJWJBOPD-UHFFFAOYSA-N 0.000 description 1
- WDJHALXBUFZDSR-UHFFFAOYSA-N Acetoacetic acid Natural products CC(=O)CC(O)=O WDJHALXBUFZDSR-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- 238000013019 agitation Methods 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 239000007900 aqueous suspension Substances 0.000 description 1
- 150000004982 aromatic amines Chemical class 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 230000003139 buffering effect Effects 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- WOWBFOBYOAGEEA-UHFFFAOYSA-N diafenthiuron Chemical compound CC(C)C1=C(NC(=S)NC(C)(C)C)C(C(C)C)=CC(OC=2C=CC=CC=2)=C1 WOWBFOBYOAGEEA-UHFFFAOYSA-N 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 238000000227 grinding Methods 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- KYYRTDXOHQYZPO-UHFFFAOYSA-N n-(2-methoxyphenyl)-3-oxobutanamide Chemical compound COC1=CC=CC=C1NC(=O)CC(C)=O KYYRTDXOHQYZPO-UHFFFAOYSA-N 0.000 description 1
- JEXVQSWXXUJEMA-UHFFFAOYSA-N pyrazol-3-one Chemical compound O=C1C=CN=N1 JEXVQSWXXUJEMA-UHFFFAOYSA-N 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 239000000523 sample Substances 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
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
- 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
- C09B67/006—Preparation of organic pigments
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Paints Or Removers (AREA)
- Pigments, Carbon Blacks, Or Wood Stains (AREA)
- Inks, Pencil-Leads, Or Crayons (AREA)
- Photoreceptors In Electrophotography (AREA)
Description
Pr- COMMONWEALTH OF AUSTRALIA PATENTS ACT 1952-69 5947f300 COMPLETE SPECIFICATION
(ORIGINAL)
Class I t. Class Application Number: Lodged: 7 qo 7 IF7 ACCcmplete Specification Lodged: D riority: Accepted: Published: 1bTh o.wisc)LLnS r~ amntskexts Made und.r Sect~on 49.
and 4e 4 hr z~b I I Related Art 04 Name of Applicant: Address of Applicant: HOECHST AKTIENGESELLSCHAFT 45 Bruningstrasse, D-6230 Frankfurt/Main Federal Republic of Germany HEINRICH REHBERG and H-ARTMUT BEHRINGER EDWD. WATERS SONS, 50 QUEEN STREET, MELBOURNE, AUSTRALIA, 3000.
Actual Inventor: Address for Service:
I
Complete Specification for the invention entitled: PROCESS FOR MAKING AZO PIGMENTS The following statement is a full description of this invention, including the best method of performing it known toI.
HOE 86/H 011 Azo pigments are made, preferably by subjecting a diazonium compound to an azo coupling reaction with a coupling component, such as an aromatic amine, acetoacetic acid arylide, naphthol, phenol or pyrazolone. This is commonly done by mixing the feed materials in aqueous phase. Reactions of this kind have long been known and described in textbooks of organic chemistry (cf. e.g. Louis and Mary Fieser, Organische Chemie, Verlag Chemie, Weinheim/Bergstrasse, 1965, pages 890 et seq., 1431, 1766 et seq.).
The coupling of components difficultly soluble in an aqueous system raises special problems. To undergo reaction, it is necessary for such coupling components to be distributed as finely as possible. This is done by adding a dispersant, emulsifier or solvent, e.g. an alcohol, or by to t15 grinding or precipitating the coupling components which are soluble in strongly alkaline media and can be precipitated by the addition of an acid. The difficult solubility of the coupling component often leads to occlusions in the pigment; as is known, the difficulty of producing pure pigments increases with a decreasing solubility of the pigment in the reaction system.
Normally, the diazonium salt solution stabler in the Sacid pH-range is allowed to run into the solution or suspension of the coupling component; the acid set free during the azo coupling reaction and -the excess acid present in the diazonium salt solution are neutralized by adding a base so as to maintain a predetermined pH. At the feed 1 G 8 40 0 S0 00 0 0 0 I6 inlet for the acid diazonium salt solution, there is always a pH-value different from that which establishes after mixing, and agitator kind and agitation velocity also influence the formation of by-products and ultimately the coloristic propertie's of the pigment to be made. In order to avoid side reactions, care is always taken to ensure that the reaction mixture remains free from diazonium compound in excess.
We have now unexpectedly found that pure azo pigmentsk free from occlusions of unreacted coupling component can be reproducibly obtained by very rapidly mixing, under certain reaction conditions, equivalent quantities of an aqueous/ acid-diazonium salt solution with an aqueous reactive suspension of a coupling component difficultly soluble in the aqueous/neutral to aqueous/acid pH-range. A difficultly soluble coupling component is one having a solubility of less than 0.1 wgt at pH 7.
The present invention provides more particularly a process for making azo pigments by subjecting a diazo component to an azo coupling reaction with the equivalent quantity of a coupling component difficultly soluble at less than 65 0 °C in the aqueous/acid and aqueous/neutral pHranges, which comprises: continuously mixing in a first reaction step, an aqueous/alkaline solution of the coupling component with an aqueous solution of an acid selected from the group consisting of acetic acid, boric acid, phosphoric acid, hydrochloric acid or sulfuric acid at a temperature lower than 65°C and within a period of less than 1 minute,
I~
1 during which the coupling component ,eo ene- precipitating at least partially as reactive matter; continuously mixing, in a second reaction step immediately following the first reaction step, the suspension obtained with an aqueous/acid solution of the diazo component at a temperature of less than 65°C within a period of less than 1 minute, and establishing a predetermined pH between 2 and 9 by controlling the flow of the mass streams of the diazo component and coupling component and thereby causing a portion of the coupling component to undergo immediate reaction to the azo pigment to be made; and reacting the balance portion of the coupling component in a post-reaction phase with unreacted diazo component to the azo pigment to be made.
Further preferred and optional features of the process s 15 of this invention provide: a) for the continuous mixing to be effected over a period of less than 6 seconed, in the second reaction step; b) for a buffering substance contributing to establishing the predetermined pH to be added during the second reaction step; c) for 60 to 98 of the coupling component to undergo immediate reaction to the azo pigment to be made, in the second reaction step; d) for the temperature during the azo coupling reaction including the post-reaction phase to be 10 to 55 0
C
during the second reaction step; 3
S-
11'
J
S.
e) for the reactive coupling component precipitated during the first reaction step, depending on its chemical composition, to have an enolate, phenolate or naphtholate group fixed to the surface of its particles.
The first processing step of this invention comprises mixing an aqueous/alkaline-solution of the difficultly soluble coupling component within a period of less than 1 minute with an aqueous, optionally buffering acid solution at temperatures of less than 65 0 C, the resulting pH-value being within the weakly acid to alkaline range (pH 4-11).
During that operation, at least a portion of the difficultly soluble coupling component is precipitated as reactive matter which is more reactive than the particles of the pure coupling component. Depending on the chemical -i r- of the coupling component, the regular finely crystalline particles have a phenolate, enolate or naphtholate group, fixed to their surface, which acts upon the electron density within the crystalline particles and renders them especially reactive.
Immediately after the mixing operation during which coupling component is precipitated, the resulting aqueous suspension is mixed with the equivalent quantity of an aqueous/acid-diazonium salt solution at a temperature of less than 65°C and within a period of less than 1 minute, the resulting pH-value varying between 2 and 9. Establishing an even narrower range depends on the diazo component and coupling component selected and the particular product to be made. It is however allowable or even obligatory for the pH 4 t:C.~hr? selected to be the higher within the limits specified the stabler the diazo component and the lower the solubility of the coupling component in the neutral range.
A portion of the azo pigment to be made is formed immediately on mixing the feed materials, and another portion is formed in a post reaction phase, depending on the specific properties of the feed materials, from diazo compound still present and coupling component precipitated as reactive matter. Although an excess of diazo component has long been held highly undesirable, we have unexpectedly found that within the pH- and temperature ranges specifically selected in this invention for the less than 1 minute rapid mixing of the feed components, the diazonium component is substantially not liable to undergo decomposition during a 0.01 1 15 hour period which is sufficiently long for the precipitated o a| reactive matter portion of the coupling component to become completely coupled in a post-reaction phase, which varies between 0.01 and 1 hour, depending on the product to be made. It is often advantageous for a portion of the product coming from the mixer to be recycled, through an intermet S diate container, if desired, in order to promote the mixing and regulate the residence time of the material in the mixer.
S k r feed materials for making the diazo component are e.g. 2,5-dichloroaniline; 2-chloro-4-nitroaniline; ~5-nitro-2-aminoanisole or 3-nitro-4-aminotoluene. The useful i coupling components should preferably be selected e.g. from 0 2-hydroxy-3-naphthoic acid anilide; 3-naphthol or aceto acetic acid-o-aniside.
Example 1 (cf. accompanying drawing) Preparation of 2-(2-methoxy-4-nitrophenylazo)-N-(2methoxy-phenyl)-3-oxobutane imide of the formula
CH
0 0 0 II II NH C CH C CH 3
N
OCH
3
NO
2 2 0'0 0. 00 0 00 .000 00 0 00 0 0 0 00 0$.
0 08D Sa 0s 00 8 ).c 134 g 0.80 mol) 5-nitro-2-aminoanisole formula of the
NH
2
OCH
3
NO
2 was suspended in 250 ml water and 210 ml hydrochloric acid (31 wgt %),the suspension was cooled by adding 400 g ice and diazotized at 5 10 0 C with 113 ml sodium nitrite solution wgt 5 g filter aid and clarifying agent (kieselguhr and active carbon) were added,.the solution was filtered and made up with ice water to 2 liters in container Next, the nitrite in excess was practically completely decomposed by adding amidosulfuric acid (aminosulfonic acid H 2
N-SO
2 0H).
172 g 0.83 mol) acetoacetic acid-o-anisidide of the formula 0 0 N
CH
3
-C-CH
2
-C-N-
OCH
3 was suspended in 530 ml water and dissolved by adding 200 ml sodium hydroxide solution (25 wgt The solution was cooled to 10°C and made up with water to 1000 ml. Within 2 hours, this solution from container (11) was introduced jointly with a mixture (coming from line 12) of 152 ml aceo tic acid (60 wgt and 400 ml water into mixer Dilute acetic acid was added as a buffering substance in quantities I° 15 monitored by means of pH-probe near the outlet of mixer (13) 0000 o°a so as to have a pH of 5.5. A portion of the coupling compo- So nent precipitated as reactive matter.
The material coming from mixer (13) was introduced into oo mixer (14) and mixed therein within 2 hours at 10 0 C with the 20 diazonium solution coming from container The product 0 leaving mixer (14) was introduced through line (15) into collecting tank The residence time in each of mixers (13) and (14) was 1 second.
The mixing operation in mixer (14) was promoted by means of a stream of auxiliary material recycled from collecting tank (16) through recycle line into mixer (14); the auxiliary material was used in a quantity (by volume) ten times larger than the quantity (by volume) of the diazonium salt used per hour. The pH in collecting tank (16) was 3.6 and the temperature was maintained at 10 0 C by adding ice.
After all materials from containers (10) and (11) and line (12) had been added, the batch in collecting tank (16) was allowed to undergo post-reaction for 20 minutes at 20 0
C
until diazo compound was no longer detectable.
The azo pigment taken from collecting tank (16) through line (18) by filtration, and dried at 100 0 C (302 g 0.78 mol) was free from occluded coupling component and had a coloring strength 10 stronger than that obtainable by conventional methods.
;e Example 2 (cf. accompanying drawing) Preparation of 1-(2-nitro-4-methylphenylazo)-2-hydroxy- 15 naphthalene of the formula
NO
«t °N
OH
0.526 mol) 3-nitro-4-aminotoluene of the formula
CH
3 3 S NO 2 NH 2 was suspended in 500 ml water and 126 ml hydrochloric acid (31 wgt and the suspension was diazotized at 5 0 C with 69 S-d "a o on 0900 0 n *00* 00 Cae C CC
CC
0ra ml sodium nitrite solution (40 wgt 5 g filter aid and clarifying agent (kieselguhr, active carbon) were added, the diazonium salt solution was filtered and made up with water to 2000 ml. The nitrite in excess was practically completely decomposed by means of amidosulfuric acid (H 2 N-SO2OH), and the diazonium salt solution was stored at 5 0 C in container g B-naphthol (0.521 mol) was dissolved in container (11) in 500 ml water and 186 ml sodium hydroxide solution (25 wgt the solution was cooled to 10 0 C and made up to 1500 ml. This solution from container (11) was introduced within 2 hours jointly with a solution (coming from line 12) of 24 g phosphoric acid (85 wgt as a buffering substance in 500 ml water into mixer a portion of the coupling 15 component precipitated as reactive matter.
The material coming from mixer (13) was introduced into mixer (14) and mixed at 10-15 0 C with the diazonium salt solution from container The product was taken from mixer (14) through line (15) and collected in collecting tank The residence time was 6 seconds in mixer (13) and 2 seconds in mixer (14).
The mixing operation in mixer (14) was promoted by means of a stream of auxiliary material recycled from collecting tank (16) through recycle line (17) into mixer (14); the auxiliary material was used in a quantity (by volume) ten times larger than the quantity (by volume) of the diazonium salt used per hour. Collecting tank (16) had initially o
I
3 Ii
LL
been charged with 250 ml water diluting the auxiliary material recycled on starting the reaction.
A pH of 8.5 8.8 was metered in collecting tank (16) which was maintained by fine control of the mass streams of acid diazonium salt solution and alkaline coupling solution.
The conversion rate of diazonium component to desirable azo pigment was about 98 at the outlet of mixer it became quantitative during a 0.6 minute post-reaction period.
The suspension was taken from collecting tank (16) through line filtered and dried at 110 0 C; the azo pigment so made was of high brillancy and obtained in a yield of 156 g (0.51 mol).
Claims (8)
1. Process for making pure azo pigments substantially free from occlusions of unreacted coupling components by subjecting a diazo component to an azo coupling reaction with the equivalent quantity of a coupling component difficulty soluble, that is, a coupling component having a solubility of less than 0.1 wgt at pH7 at temperatures less than 65°C in the aqueous/acid and aqueous/neutral pH-ranges, which comprises: continuously mixing, in a first reaction step, an aqueous/alkaline solution of the coupling component with an aqueous solution of an acid selected from the group consisting of acetic acid, boric acid, phosphoric acid, hydrochloric acid or sulfuric acid at a temperature lower than 65°C and within a period of less than 1 minute, the resulting pH value being within the weakly acid to alkaline range, during which the coupling component commences precipitating at least partially as reactive matter; continuously mixing, in a second reaction step immediately following the first reaction step, the suspension obtained with an aqueous/acid solution of the diazo component at a temperature of less than 65°C within a period of less than 1 minute, and establishing a predetermined pH between 2 and 9 by controlling the flow of the mass streams of the diazo component and coupling component and thereby causing a portion of the coupling component to undergo immediate reaction to the azo pigment to be made; and reacting the balance portion of the coupling component in a post-reaction phase with unreacted diazo component to the azo pigment to be made.
2. Process as claimed in claim 1, wherein the continuous mixing is effected over a period of less than 6 seconds, in the second reaction step. .1
3. Process as claimed in claim 1 or 2, wherein a buffering substance contributing to establishing the predetermined pH is added during the second reaction step.
4. Process as claimed in at least one of the preceding claims, wherein 60 to 98 of the coupling component un- dergoes immediate reaction to the azo pigment to be ma- de, in the second reaction step.
Process as claimed in at least one of the' preceding claims, wherein the temperature during the azo coupling reaction including the post-reaction phase is 10 to during the second reaction step.
6. Process as claimed in at least one of the preceding claims, wherein, depending on its chemical composition, the reactive coupling component precipitated during the first reaction step has an enolate, phenolate or naphtholate group fixed to the surface of its particles.
7. Process as claimed in at least one of the preceding claims conducted substantially as described in Example 1 or 2 herein.
8. Azo pigments whenever obtained by a process as claimed Ii j' in at least one of the preceding claims. DATED this 30th day of April 1987. SIHOECHST AKTIENGESELLSCHAFT SEDWD. WATERS SONS PATENT ATTORNEYS QUEEN STREET MELBOURNE. VIC. 3000.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE3615100 | 1986-05-03 | ||
| DE3615100 | 1986-05-03 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| AU7240787A AU7240787A (en) | 1987-11-05 |
| AU594760B2 true AU594760B2 (en) | 1990-03-15 |
Family
ID=6300159
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AU72407/87A Ceased AU594760B2 (en) | 1986-05-03 | 1987-05-01 | Process for making azo pigments |
Country Status (8)
| Country | Link |
|---|---|
| EP (1) | EP0244687B1 (en) |
| JP (1) | JPH0784566B2 (en) |
| KR (1) | KR960008248B1 (en) |
| AU (1) | AU594760B2 (en) |
| DE (1) | DE3782966D1 (en) |
| DK (1) | DK168394B1 (en) |
| ES (1) | ES2037023T3 (en) |
| IN (1) | IN169308B (en) |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IN169307B (en) * | 1986-05-03 | 1991-09-28 | Hoechst Ag | |
| DE3932829C1 (en) * | 1989-09-30 | 1991-05-02 | Ciba-Geigy Ag, Basel, Ch | |
| DE4447593C2 (en) * | 1994-10-05 | 2000-12-07 | Clariant Gmbh | Toner for electrophotographic developers containing an azo yellow pigment |
| US6099635A (en) * | 1999-04-09 | 2000-08-08 | Lonza Ag | Acetoacetylated suspensions in pigment applications |
| JP2006028341A (en) * | 2004-07-16 | 2006-02-02 | Toyo Ink Mfg Co Ltd | Disazo pigment production method and disazo pigment |
| GB0416256D0 (en) * | 2004-07-20 | 2004-08-25 | Avecia Ltd | Manufacturing process |
| DE602005025919D1 (en) * | 2004-12-03 | 2011-02-24 | Canon Kk | PREPARATION FOR AZOPIGMENT DISPERSION |
| JP4533303B2 (en) * | 2004-12-03 | 2010-09-01 | キヤノン株式会社 | Method for producing azo pigment dispersion |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AU7240687A (en) * | 1986-05-03 | 1987-11-05 | Hoechst Aktiengesellschaft | Process for making azo pigments |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2174954A (en) * | 1937-03-22 | 1939-10-03 | Harmon Color Works Inc | Azo pigment and method of preparing |
| DE1085278B (en) * | 1958-03-08 | 1960-07-14 | Hoechst Ag | Process for the continuous production of azo pigments |
| DE2629076B2 (en) * | 1976-06-29 | 1978-04-27 | Basf Farben + Fasern Ag, 2000 Hamburg | Process for the production of a disazo pigment with improved application properties |
| US4395264A (en) * | 1981-11-06 | 1983-07-26 | Basf Wyandotte Corporation | Azo coupling process |
| GB2129434B (en) * | 1982-10-08 | 1986-04-16 | Ciba Geigy Ag | Production of azo compounds |
-
1987
- 1987-03-26 IN IN220/MAS/87A patent/IN169308B/en unknown
- 1987-04-18 DE DE8787105766T patent/DE3782966D1/en not_active Expired - Lifetime
- 1987-04-18 ES ES198787105766T patent/ES2037023T3/en not_active Expired - Lifetime
- 1987-04-18 EP EP87105766A patent/EP0244687B1/en not_active Expired - Lifetime
- 1987-05-01 KR KR1019870004280A patent/KR960008248B1/en not_active Expired - Fee Related
- 1987-05-01 DK DK223487A patent/DK168394B1/en not_active IP Right Cessation
- 1987-05-01 AU AU72407/87A patent/AU594760B2/en not_active Ceased
- 1987-05-06 JP JP62109069A patent/JPH0784566B2/en not_active Expired - Fee Related
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AU7240687A (en) * | 1986-05-03 | 1987-11-05 | Hoechst Aktiengesellschaft | Process for making azo pigments |
Also Published As
| Publication number | Publication date |
|---|---|
| DK223487D0 (en) | 1987-05-01 |
| DK223487A (en) | 1987-11-04 |
| EP0244687A2 (en) | 1987-11-11 |
| EP0244687A3 (en) | 1990-11-14 |
| ES2037023T3 (en) | 1993-06-16 |
| JPS62263261A (en) | 1987-11-16 |
| EP0244687B1 (en) | 1992-12-09 |
| KR960008248B1 (en) | 1996-06-21 |
| DK168394B1 (en) | 1994-03-21 |
| IN169308B (en) | 1991-09-28 |
| KR870011207A (en) | 1987-12-21 |
| JPH0784566B2 (en) | 1995-09-13 |
| DE3782966D1 (en) | 1993-01-21 |
| AU7240787A (en) | 1987-11-05 |
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