GB1600923A - Monoazo dyes based on dialkoxy-substituted acetoacetarylides as coupling components - Google Patents
Monoazo dyes based on dialkoxy-substituted acetoacetarylides as coupling components Download PDFInfo
- Publication number
- GB1600923A GB1600923A GB17961/78A GB1796178A GB1600923A GB 1600923 A GB1600923 A GB 1600923A GB 17961/78 A GB17961/78 A GB 17961/78A GB 1796178 A GB1796178 A GB 1796178A GB 1600923 A GB1600923 A GB 1600923A
- Authority
- GB
- United Kingdom
- Prior art keywords
- compound
- chlorine
- bromine
- general formula
- hydrogen
- 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
- 230000008878 coupling Effects 0.000 title claims description 10
- 238000010168 coupling process Methods 0.000 title claims description 10
- 238000005859 coupling reaction Methods 0.000 title claims description 10
- 239000000975 dye Substances 0.000 title description 6
- NYGZLYXAPMMJTE-UHFFFAOYSA-M metanil yellow Chemical group [Na+].[O-]S(=O)(=O)C1=CC=CC(N=NC=2C=CC(NC=3C=CC=CC=3)=CC=2)=C1 NYGZLYXAPMMJTE-UHFFFAOYSA-M 0.000 title description 3
- 239000000460 chlorine Substances 0.000 claims description 24
- 229910052801 chlorine Inorganic materials 0.000 claims description 14
- 150000001875 compounds Chemical class 0.000 claims description 14
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 13
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 10
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 10
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 10
- 229910052794 bromium Inorganic materials 0.000 claims description 10
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 10
- 229910052739 hydrogen Inorganic materials 0.000 claims description 8
- 239000001257 hydrogen Substances 0.000 claims description 8
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 8
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 7
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 7
- 239000000203 mixture Substances 0.000 claims description 6
- 150000001989 diazonium salts Chemical class 0.000 claims description 5
- 238000000034 method Methods 0.000 claims description 5
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 5
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 4
- 238000009472 formulation Methods 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 3
- 239000003973 paint Substances 0.000 claims description 3
- 239000000049 pigment Substances 0.000 claims description 3
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 3
- 150000001412 amines Chemical class 0.000 claims description 2
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 2
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 239000008199 coating composition Substances 0.000 claims description 2
- 238000004043 dyeing Methods 0.000 claims description 2
- 239000000835 fiber Substances 0.000 claims description 2
- -1 nitro, methyl Chemical group 0.000 claims description 2
- 239000004033 plastic Substances 0.000 claims description 2
- 229920003023 plastic Polymers 0.000 claims description 2
- 239000004753 textile Substances 0.000 claims description 2
- 239000012463 white pigment Substances 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims 1
- 239000000463 material Substances 0.000 claims 1
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 8
- 239000000243 solution Substances 0.000 description 7
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 239000000725 suspension Substances 0.000 description 4
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 229960000583 acetic acid Drugs 0.000 description 3
- 239000012954 diazonium Substances 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 238000000576 coating method Methods 0.000 description 2
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
- IIACRCGMVDHOTQ-UHFFFAOYSA-N sulfamic acid Chemical compound NS(O)(=O)=O IIACRCGMVDHOTQ-UHFFFAOYSA-N 0.000 description 2
- 239000001060 yellow colorant Substances 0.000 description 2
- QMBANXLJKPZBTA-UHFFFAOYSA-N 2,4-dimethoxy-3-oxo-n-phenylbutanamide Chemical compound COCC(=O)C(OC)C(=O)NC1=CC=CC=C1 QMBANXLJKPZBTA-UHFFFAOYSA-N 0.000 description 1
- BEKMTRPOJAKFPZ-UHFFFAOYSA-N 2-(3-phenyl-1,2,4-oxadiazol-5-yl)aniline Chemical compound NC1=CC=CC=C1C1=NC(C=2C=CC=CC=2)=NO1 BEKMTRPOJAKFPZ-UHFFFAOYSA-N 0.000 description 1
- YLQDROQQHPYPHU-UHFFFAOYSA-N 4-chloro-2-(3-phenyl-1,2,4-oxadiazol-5-yl)aniline Chemical compound NC1=CC=C(Cl)C=C1C1=NC(C=2C=CC=CC=2)=NO1 YLQDROQQHPYPHU-UHFFFAOYSA-N 0.000 description 1
- RXQNKKRGJJRMKD-UHFFFAOYSA-N 5-bromo-2-methylaniline Chemical compound CC1=CC=C(Br)C=C1N RXQNKKRGJJRMKD-UHFFFAOYSA-N 0.000 description 1
- IOVCWXUNBOPUCH-UHFFFAOYSA-M Nitrite anion Chemical compound [O-]N=O IOVCWXUNBOPUCH-UHFFFAOYSA-M 0.000 description 1
- 238000007605 air drying Methods 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- 238000006193 diazotization reaction Methods 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 239000000976 ink Substances 0.000 description 1
- 229920000098 polyolefin Polymers 0.000 description 1
- 229920000915 polyvinyl chloride Polymers 0.000 description 1
- 239000004800 polyvinyl chloride Substances 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 235000010288 sodium nitrite Nutrition 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- 239000001052 yellow pigment 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
- C09B29/00—Monoazo dyes prepared by diazotising and coupling
- C09B29/32—Monoazo dyes prepared by diazotising and coupling from coupling components containing a reactive methylene group
- C09B29/33—Aceto- or benzoylacetylarylides
- C09B29/335—Aceto- or benzoylacetylarylides free of acid groups
- C09B29/337—Carbocyclic arylides
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B29/00—Monoazo dyes prepared by diazotising and coupling
- C09B29/0003—Monoazo dyes prepared by diazotising and coupling from diazotized anilines
- C09B29/0011—Monoazo dyes prepared by diazotising and coupling from diazotized anilines from diazotized anilines directly substituted by a heterocyclic ring (not condensed)
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Paints Or Removers (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Coloring (AREA)
Description
(54) MONOAZO DYES BASED ON DIALKOXY-SUBSTITUTED
ACETOACETARYLIDES AS COUPLING COMPONENTS
(71) We, BASF AKTIENGESELLSCHAFT, a German Joint Stock Company of 6700 Ludwigshafen, Federal Republic of Germany, do hereby declare the invention, for which we pray that a patent may be granted to us, and the method by which it is to be performed, to be particularly described in and by the following statement: The present invention relates to monoazo dyes.
According to the invention there are provided compounds of the general formula
where R is phenyl which is optionally substituted by chlorine, bromine, nitro, methyl, ethyl, methoxy or ethoxy; R1 is hydrogen, chlorine, bromine, nitro, trifluoromethyl, methyl, carbamoyl or sulfamoyl; R2 is hydrogen, chlorine, bromine or nitro; R3 is alkyl of 1 to 4 carbon atoms; and X is hydrogen, chlorine or bromine.
Examples of alkyl R3 are ethyl, propyl, butyl and preferably methyl. The compounds of the formula I may be manufactured by reacting a diazonium compound of an amine of the formula II
with a coupling component of the formula III
The compounds of the formula I are substantially insoluble and exhibit pigment properties. They are distinguished by great brilliance, excellent fastness to weathering both in full shades and when blended with white pigment, and mav in particular be used for such applications as paints (e.g. external paints), printing inks, surface coating compositions (e.g. for air-drying coatings) and, in some cases, the coloring of plastics, eg. polyolefins or rigid polyvinyl chloride.
Compounds of particular importance are those of the formula Ia
and preferably of the formula
where R4 is phenyl which is optionally substituted by chlorine or methyl, R5 is hydrogen or chlorine and R2, R3 and X have the above meaning.
In the Examples which follow, parts and percentages are by weight, unless stated otherwise.
EXAMPLE 1.
5.7 parts of 2-(3-phenyl-1,2,4-oxdiazolyl)aniline are dissolved in 11 parts of dimethylformamide and the solution is run into a mixture of 60 parts of ice, 50 parts of water, 10.8 parts of concentrated hydrochloric acid and 12 parts of glacial acetic acid, whilst stirring thoroughly. 9 parts of 23% strength NaNO2 solution are added slowly to the resulting suspension at 0--50C and the batch is then stirred for 4 hours. The excess nitrite is destroyed by adding 0.7 part of amido-sulfonic acid.
5.8 parts of 2,4-dimethoxyacetoacetanilide are dissolved in 60 parts of water by means of 2.6 parts of sodium hydroxide, 25 parts of ice are added and the 2.4dimethoxvacetoacetanilide is reprecipitated by means of 8 parts of 50% strength acetic acid. This suspension is run into the diazonium salt solution described above and the pH is then brought to about 4 by means of 50% strength sodium hydroxide solution.
The batch is stirred for 30 minutes and the product is filtered off, washed with water and dried at 800C under reduced pressure. 11.2 parts of a brilliant yellow colorant of the formula
are obtained; this product exhibits excellent lightfastness and fastness to weathering when used in a surface coating.
EXAMPLE 2.
27 parts of 4-chloro-2-(3-phenyl-1,2,4-oxdiazolyl)-aniline are introduced into 100
parts of concentrated sulfuric acid at 200 C, the mixture is cooled to OOC and diazo
tization is carried out by adding 32 parts of nitrosylsulfuric acid. The viscous dia
zonium salt solution is stirred for 3 hours at 5"C and then poured onto 600 parts of
ice in 200 parts of water, and 2 parts of amidosulfonic acid are added.
24 parts of 2,dimethoxyacetoacetanillde are dissolved in 300 parts of water by
means of 13 parts of sodium hydroxide solution, 120 parts of ice are added and the 2,4-dimethoxvacetoacetanilide is reprecipitated by means of 40 parts of 50 /^ strength acetic acid. This suspension is run into the diazonium salt suspension described above and the pH is brought to 4 by adding sodium hydroxide solution. The batch is then stirred for 30 minutes and the product is filtered off, washed with water and dried at 80"C under reduced pressure.
52 parts of a brilliant yellow pigment of the formula
which has excellent lightfastness and fastness to weathering are obtained
Using the method described in Example 1, yellow colorants are obtained from the diazo components and coupling components shown in the Table which follows.
Example Diazo component Coupling component
No.
3 O--N O\CH3 CH3COCH2COllH 001 OCH OCH 4 11 CH3COCH2CONH X CX3 OCH O-N 3 CH3CoCH2Coc: & BR< 5 C1u\ CH?COCH2COi NH2 OCH 6 I1 CHCOCH2COWH X C1 OCH 3 7 O--N OH %Ny$o1;)y OH5COCH2CO 0 H3 Example Diazo component Coupling component
No.
C--N 02N OOH3 8 < 2 < CHDCOCH2CONH 4 OCH3 Cl OCH 0d \ ) 9 2C0NH Q NH2 OCH 10 Cl < X CH3COCH2CON oc5 Cl OCH 11 1f CH5COCH2CONH 9C1 OCH 3 OCH 12 Br CH#OOH2CONH OCH ) 2 Br 0-N Ci '1 13 ONO NH2 OCH5 14 If CH3COCH2COTAQCi OCH3 Example Diazo component Coupling component
No.
OCH 15 00N\0r CH3COCH2CONHWC 2 OCH OCH3 16 n CH3CoCH2CONH4ocH3 17 X 2 n NH2 18 0N 10 10J 19 N I? OCH 20 n CH3COCH2CONH4C1 OCH3 O N CK, n 21 XNH2NX OCH3 NH20 OCH 22 tt CH3COCH2CONHoCH3 Example
No. Diazo component Coupling component
OCH 0-N 23 (D%y0H5 CE3COCH2CONE e oCH3 2 I' 24 [\%y\NQ3 OCH 2 3 OCH3 25 e CH3COCH2CONH X C1 OCH OCH3 3 26 n CH3COCH2CONH ss CCr.
0-N .27 Cl OH3COCH2COtOCH5 NH2 28 O :u'n OCH 29 n CH3COCH2CONH Ci OCH.3 Example Diazo component Coupling component
OCH C1 C1\ CH3COCH2CONH 1 Cl OCH3 OCH 31 n CHCOCH2CONHOCH 3 32 cTho TI NH2 CH3 C1 < 3 34 IO--N n Cr oo 3 35 TI CF
The following compounds may be obtained analogously.
Example
No. B1 B2 A
36 4-C1 6-Cl C6H5 37 n -O-CII3 38 II I! ? Z CH3 39 tl 39 tr (I-C1 40 1? n n C1 41 n TI Cl 42 1? '1 43 TI Ir Example B1 B2 A
No.
44 4-C1 6-C1 -G-NO2 45 re 1' - -O2H5 46 U U -OCH3 47 n n OCH 48 TI n C1 0O2H5 49 n n ; Cl 50 n n -b-CX) 51 4-Br 6-Br 52 TI TI --OH3 53 TI TI n -00113 Example
No. B1 B2 A
54 4-Br 6-Br 55 ,1 Cl Cl 56 . n QTI C1 57 4-No2 H 58 It I, 59 n TI - O-CH3 60 n TI G - OCH3 61 4-No2 6-No2 C 6H5 62 n fl p CH3 63 4-Cl 6-Cl --OC2H5 Example B1 B2 A
No.
64 4-No2 6-No2 65 n TI - reOCH, 66 4-0-1 6-No2 O6H5 67 t C1 -Cl 68 4-CF3 H C6H5 69 TI -O-C=3 70 t tl ~p CH3 71 TI TI 72 rr n 1 C1 Cl Example No .
Having regard to our copending British Patent Application No. 11303/77 (Serial
No. 1,574,629) we make no claim herein to the dye of the formula
Nor do we make any claim to dye formulations for dyeing and printing cellulosic textiles or to uniformly dyed cellulosic fibers wherein the dye used has the formula
where Z is H or NO2 and R10 is phenyl substituted by methoxy and/or ethoxy and optionally by chlorine and/or bromine.
Subject to this disclaimer, WHAT WE CLAIM IS:
1. A compound of the general formula:
**WARNING** end of DESC field may overlap start of CLMS **.
Claims (10)
1. A compound of the general formula:
in which R is phenyl which is optionally substituted by chlorine, bromine, nitro, methyl, ethyl, methoxy or ethoxy; Rl is hydrogen, chlorine, bromine, nitro, trifluoromethyl, methyl, carbamoyl or sulfamoyl; R2 is hydrogen, chlorine, bromine or nitro;
R3 is alkyl of 1 to 4 carbon atoms; and X is hydrogen, chlorine or bromine.
2. A compound as claimed in claim 1 and having the general formula:
in which R4 is phenyl which is optionally substituted by chlorine or methyl, R5 is hydrogen or chlorine and R2, R3 and X are as defined in claim 1.
3. A compound as claimed in claim 1 and having the general formula:
in which R2, R4 and R5 are as defined in claim 2.
4. A compound as claimed in claim 1 and identified in any one of the foregoing
Examples 2 to 76.
5. A process for the manufacture of a compound as claimed in claim 1, wherein a diazonium compound of an amine of the general formula:
in which R. R1 and R2 are as defined in claim 1, is reacted with a coupling component of the general formula
in which R3 is as defined in claim 1.
6. A process as claimed in claim 5 carried- out substantially as described in any one of the foregoing Examples.
7. A compound as claimed in claim 1 and whenever obtained by a process as claimed in claim 5 or claim 6.
8. A pigment formulation which comprises a white pigment and a compound asclaimed in any one of claims 1 to 4 and 7.
9. A pigment formulation as claimed in claim 8 which is in the form of a paint, surface coating composition or printing ink.
10. A plastics material colored by the presence therein of a compound as claimed in any one of claims 1 to 4 and 7.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19772720659 DE2720659A1 (en) | 1977-05-07 | 1977-05-07 | PIGMENT DYES |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1600923A true GB1600923A (en) | 1981-10-21 |
Family
ID=6008352
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB17961/78A Expired GB1600923A (en) | 1977-05-07 | 1978-05-05 | Monoazo dyes based on dialkoxy-substituted acetoacetarylides as coupling components |
Country Status (7)
| Country | Link |
|---|---|
| JP (1) | JPS53138433A (en) |
| BE (1) | BE866667A (en) |
| DE (1) | DE2720659A1 (en) |
| FR (1) | FR2389663A1 (en) |
| GB (1) | GB1600923A (en) |
| IT (1) | IT1094808B (en) |
| NL (1) | NL7804779A (en) |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CH611324A5 (en) * | 1974-04-09 | 1979-05-31 | Basf Ag | |
| AT350998B (en) * | 1976-03-18 | 1979-06-25 | Basf Ag | DYE PREPARATIONS FOR CELLULOSE AND CELLULOSE-CONTAINING TEXTILE MATERIAL |
-
1977
- 1977-05-07 DE DE19772720659 patent/DE2720659A1/en not_active Withdrawn
-
1978
- 1978-04-28 IT IT22882/78A patent/IT1094808B/en active
- 1978-05-03 FR FR7813074A patent/FR2389663A1/fr not_active Withdrawn
- 1978-05-03 NL NL7804779A patent/NL7804779A/en not_active Application Discontinuation
- 1978-05-03 BE BE187357A patent/BE866667A/en unknown
- 1978-05-04 JP JP5285478A patent/JPS53138433A/en active Pending
- 1978-05-05 GB GB17961/78A patent/GB1600923A/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| JPS53138433A (en) | 1978-12-02 |
| IT1094808B (en) | 1985-08-10 |
| IT7822882A0 (en) | 1978-04-28 |
| BE866667A (en) | 1978-11-03 |
| NL7804779A (en) | 1978-11-09 |
| FR2389663A1 (en) | 1978-12-01 |
| DE2720659A1 (en) | 1978-11-09 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| CSNS | Application of which complete specification have been accepted and published, but patent is not sealed |