CA1135688A - Disazo compounds, process for their manufacture and their use - Google Patents
Disazo compounds, process for their manufacture and their useInfo
- Publication number
- CA1135688A CA1135688A CA000359611A CA359611A CA1135688A CA 1135688 A CA1135688 A CA 1135688A CA 000359611 A CA000359611 A CA 000359611A CA 359611 A CA359611 A CA 359611A CA 1135688 A CA1135688 A CA 1135688A
- Authority
- CA
- Canada
- Prior art keywords
- compound
- methyl
- formula
- ethyl
- 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
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)
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Inks, Pencil-Leads, Or Crayons (AREA)
- Coloring (AREA)
Abstract
Abstract of the disclosure Diazotizing of lower alkyl 3-nitro-4-amlno-benzoates. and coupling onto bis-(acetoacetyl)-p-phenylene diamine, which may be substituted by halogen, lower alkyl or lower alkoxy, leads to disazo compounds which are pigments or high tincto-rial strength and good fastness to light, weathering and solvents,
Description
11356~8 Subject of the invention are disazo compounds of the formula I COOR
¦ COOR
¦ COOR
2 ~
N N No2 ,~ X ~
H3C~ NH~NH~h~ CH3 O O O O
in which R is alkyl with from 1 to 4 carbon atoms, X and Y are hydrogen, chlorine, bromine, methyl, ethyl, methoxy or ethoxy.
The invention further relates to a process for the manufacture of the abo~e-mentioned disa70 compounds, which comprises ~iazotizingcompollnds of the formula II
~2 20 ~ H2 II
ROOC
in which R has the meaning mentioned for formula I, and coupling two molar equivalents Or the diazonium compound obtained, or of the mixture of two or more diazonium compounds from compounds of formula II with one molar equivalent of a compound, or a mixture of two or more compounds of the formula III
O O ~ ~H ~ ~ ~ CH3 III
in which X and Y are 2S defined f`or formula I abo~e.
~L3~61~3 Another subject of the invention is the use of the disazo compounds of the invention as colorants, espe-cially as pigments.
Suitable amines of the formula II are, for example:
N N No2 ,~ X ~
H3C~ NH~NH~h~ CH3 O O O O
in which R is alkyl with from 1 to 4 carbon atoms, X and Y are hydrogen, chlorine, bromine, methyl, ethyl, methoxy or ethoxy.
The invention further relates to a process for the manufacture of the abo~e-mentioned disa70 compounds, which comprises ~iazotizingcompollnds of the formula II
~2 20 ~ H2 II
ROOC
in which R has the meaning mentioned for formula I, and coupling two molar equivalents Or the diazonium compound obtained, or of the mixture of two or more diazonium compounds from compounds of formula II with one molar equivalent of a compound, or a mixture of two or more compounds of the formula III
O O ~ ~H ~ ~ ~ CH3 III
in which X and Y are 2S defined f`or formula I abo~e.
~L3~61~3 Another subject of the invention is the use of the disazo compounds of the invention as colorants, espe-cially as pigments.
Suitable amines of the formula II are, for example:
3-Nitro-4-aminobenzoic acid methyl ester 3-Nitro-4-aminobenzoic acid ethyl ester 3-Nitro-4-aminobenzoic acid-n-propyl ester 3~Nitro-4-aminobenzoic acid-isopropyl ester 3-Nitro-4-aminobenzoic acid-n-butyl ester 3-Nitro-4-aminobenzoic acid-isobutyl ester 3-Nitro-4-aminobenzoic acid-1'-methyl-propyl ester.
The amine of the formula II may be diazotized for example with alkali metal nitrites or lower alkyl nitrites with sufficiently strong acids, especially a mineral acid, but also with nitrosylsulfuric acid.
In this process step as well as in the subsequent coupling it may be adv-antageous to add surface-active agents, such as non-ionic, anionic or cationic dis-persing agents. The diazotization is suitably carried out at -10 to ~30C, and the coupling is effected at 0 to 40C.
As coupling components there may be used, for examp]e:
1,4-Bisacetoacetylaminobenzene, 1,4-Bisacetoacetylamino-2-chlorobenzene, 1,4-Bisacetoacetylamino-2,5-dichlorobenzene, 1,4-Bisacetoacetylamino-2-methylbenzene, 1,4-Bisacetoacetylamino-2,5~dimethylbenzene, 1,4-Bisacetoacetylamino-2-methoxybenzene, 1,4-Bisacetcacetylamino-2,5-dimethoxybenze, 1,4-Bisacetoacetylamino-2--bromobenzene, 1,4-Bisacetoacetylamino-2,5-dibromobenzene 1,4-Bisacetoacetylamino-2-ethylbenzene, 1,4-Bis~cetoacetylamino-2~ethoxyben~e, 1,4-Bisacetoacetylamino-2-methoxy-5-methylbenzene, 1~3~t3 1,4-Bisacetoacetylamino-2~chloro-5-methylbenzene and 1,4-Bisacetoacetylamino-2-chloro-5-methoxybenzene.
The diazotization and coupling may also be carried out in the presence of suitable organic solvents, such as glacial acetic acid, lower alkanols, dioxan, formamide, dimethyl formamide, dimethyl sulfoxide, pyridine or N-methyl-pyrrolidone. In order to obtain the full tinctorial strength, it is often advantageous to heat the coupling mixture for some time, for example by boiling it or maintaining it under pressure at temperatu-res of more than 100C, optionally in the presence of organic solvents, such as lower alkanols, for example ethanol or isobutanol, halogenated aromatic hydrocarbons, 1~ such as chlorobenzene or dichlorobenzenes, e.g. o-dichlo-robenzene, dimethyl formamide, N-methyl pyrrolidone or in the presence of resin soap. Particularly pure pigments of high tinctorial strength are obtained with the products of the invention, if after coupling the moist press cakes or the dried powders are subjected to a thermal aftertreatment with organic solvents, such as alcohols, above all lower alkanols, pyridine, glacial acetic acid, dimethyl formamide, N-methyl pyrrolidone, dimethyl sulfoxide, halogenated aromatic hydrocarbons ~5 such as chlorobenzene or dichlorobenzenes t for example o-dichlorobenzene, or nitrobenzene, or if the pigments are subsequently ground with the addition of grindirg auxiliaries.
The term "lower" relating to alkyl radicals includes groups of from 1 to 5, especially 1 to 4, carbon atoms.
The pigments may also be prepared in the presence of a carrier r~.ater~a , for example baryte.
The novel compounds are water-insoluble and insoluble in the common organic solvents and are suitable for 1~L3561~8 pigmenting printing inks, varnished and dispersion ~ paints, for dyeing caoutchouc, plastics and natural ¦ or synthetic resins.
, 5 They are further appropriate for the pigment printing l on substrates, especially textile fiber materials or other flat articles, such as paper.
The pigments may also be used for other fields of application, for example in a finely devided form of the dyeing of rayon of viscose or cellulose ethers or esters, polyamides, polyurethanes, polyglycol terephtha-lates or polyacrylonitriles in the spinning mass, or for the dyeing of paper.
The pigments have a high tinctorial strength and can easily be processed in the mediums mentioned above.
The dyeings have a very good fastness to light and weather and are resistant to the influence of chemicals, especially to solvents.
The following Examples illustrate the invention, the percentages relating to the weight. Temperatures are given in C.
Example 1 10.5 grams of 3-nitro~ aminobenzoic acid ethyl ester are stirred for 1 hour at 10C in a mixture of 80 ml of glacia~l acetic acid and 15 ml of 31 % hydrochloric acid.
Thereafter 10 ml of 5N sodium nitrite solution are rapidly added dropwise, and stirring is continued for 30 minutes i (Disazo solution~. 7.3 g of 1,4-bisaceto-acetylamino-benzene are suspensed in 200 ml of water and dissolved with 5 ml of 33 % sodium hydroxide solution. For coupling the above-menticned d~ Sa70 solution is introduced into a stirring vessel and mixed with 200 ml of ice water and 10 ml of a 10 ~ aqueous solution of oleyl alcohol which h2s been re~cted with 30 mols of ethylene oxide.
Within one hour the alkaline solution of the 1,4-bi~-aceto-acetylamino-benzene is added dropwise, while maintaining the pH at about 3 - 4, with a 5 % aqueous solution of sodium acetate. After finishing the coupling stirring is continued for 30 minutes, the product is suction-filtered and washed with water until salt-free.
The press cake is suspensed in 800 ml of dimethyl formamide and after heating to 130, it is maintained at this temperature for 10 minutes. The pigment is suction-filtered again, washed with dimethyl formami,de, methanol and water and dried. Yield: 17.2 g of an intensely reddish yellow pigment of the formula 1 ' CC2H5 O2N ~ ~
,~
~I3~ H ~ MH ~ ~ CH3 O O
Example 2 l9,G g of 3-nitro-4-aminobenzoic acid methyl ester are stirred in a mix'cure of 160 ml of glacial acetic acid and 30 ml of 30 ~ hydrochloric acid. The reaction mix-ture is cooled to 10 and under the surface of this mixture there is rapidly introduced a solution of 20 ml of 5 :~50W.'_~. nitrite (diazo component.) 1~3~i61~3 j 16 g of 1,4-bisaceto-acetyl-amino-2-methoxy~benzene are dissol~ed in a mixture of 300 ml of' water and ' 10 ml of 33 % sodium hydroxide solution (coupling component). For coupling there are first introduced into a stirring vessel 300 ml of ice water, 30 ml of 2 N-sodium acetate solution, 6 ml of glacial acetic acid and 20 ml of a 10 % aqueous solution of oleyl alcohol which has been reacted with 30 mols of ethylene oxide. At 10~
the solutions of the diazo and the coupling componenet flow within one hour simultaneously to the buffer mixture. After coupling, the product is heated for 30 minutes to 80 and suction-filtered. The pigment is dried at 70, heated for a short time to 110 in 400 ml of N-methylpyrrolidone, suction-filtered, washed with methanol and water and dried. 34.8 g of reddish-yellow pigment with high tinctorial strength of the formula COOC
l COOC~3 2 ~ ~ ~ N02 N
~3C ~ ~ NH ~ NH ~ CH3 O O O O
are obtained.
The following table gives further Examples of disazo compounds which are o~tained by coupling th.e diazotized aromatic amines (diazo component) of the formula II with the coupling componen~ of the formula III:
1 ~356~3 ExampleFormula II Formula III tint ! No. R X Y
____ _ _. __ i 3 CH3 H H reddish-yellow CH3 Cl H ..
CH3 052H5 H orange 10 6 CH3 CH3 H reddish-yellow 7 CH3 Cl Cl yellow 8 CH3 OCH3 OCH3 yellowish-brown 9 CH3 CH3 CH3 orange C2H~ Cl H reddish-yellow 201~ C2H5 CH3 H yellowish~
orange 12 C2H5 OCH3 H orange 13 C2H5 Cl Cl greeni.sh-, yellow 14 C2H5 CH3 CH3 yellowish~
orange C2H5 OCH3 OCH3 yellowish-brown 3016 C2H5 Br H reddish-yellow 17 CH3 OCH3 CH3 orange t 18 n C3H7 H H reddish-yellow 19 n~C4H9 ~ H
il3S6~8 g .
ExampleFormula II Formula III tint No. R X Y
20 CH3 Cl OCH3 yello~ish-orange 21C2~5 C2H5 H reddish-- yello~7 22C2H5 Cl CH3 yello~7
The amine of the formula II may be diazotized for example with alkali metal nitrites or lower alkyl nitrites with sufficiently strong acids, especially a mineral acid, but also with nitrosylsulfuric acid.
In this process step as well as in the subsequent coupling it may be adv-antageous to add surface-active agents, such as non-ionic, anionic or cationic dis-persing agents. The diazotization is suitably carried out at -10 to ~30C, and the coupling is effected at 0 to 40C.
As coupling components there may be used, for examp]e:
1,4-Bisacetoacetylaminobenzene, 1,4-Bisacetoacetylamino-2-chlorobenzene, 1,4-Bisacetoacetylamino-2,5-dichlorobenzene, 1,4-Bisacetoacetylamino-2-methylbenzene, 1,4-Bisacetoacetylamino-2,5~dimethylbenzene, 1,4-Bisacetoacetylamino-2-methoxybenzene, 1,4-Bisacetcacetylamino-2,5-dimethoxybenze, 1,4-Bisacetoacetylamino-2--bromobenzene, 1,4-Bisacetoacetylamino-2,5-dibromobenzene 1,4-Bisacetoacetylamino-2-ethylbenzene, 1,4-Bis~cetoacetylamino-2~ethoxyben~e, 1,4-Bisacetoacetylamino-2-methoxy-5-methylbenzene, 1~3~t3 1,4-Bisacetoacetylamino-2~chloro-5-methylbenzene and 1,4-Bisacetoacetylamino-2-chloro-5-methoxybenzene.
The diazotization and coupling may also be carried out in the presence of suitable organic solvents, such as glacial acetic acid, lower alkanols, dioxan, formamide, dimethyl formamide, dimethyl sulfoxide, pyridine or N-methyl-pyrrolidone. In order to obtain the full tinctorial strength, it is often advantageous to heat the coupling mixture for some time, for example by boiling it or maintaining it under pressure at temperatu-res of more than 100C, optionally in the presence of organic solvents, such as lower alkanols, for example ethanol or isobutanol, halogenated aromatic hydrocarbons, 1~ such as chlorobenzene or dichlorobenzenes, e.g. o-dichlo-robenzene, dimethyl formamide, N-methyl pyrrolidone or in the presence of resin soap. Particularly pure pigments of high tinctorial strength are obtained with the products of the invention, if after coupling the moist press cakes or the dried powders are subjected to a thermal aftertreatment with organic solvents, such as alcohols, above all lower alkanols, pyridine, glacial acetic acid, dimethyl formamide, N-methyl pyrrolidone, dimethyl sulfoxide, halogenated aromatic hydrocarbons ~5 such as chlorobenzene or dichlorobenzenes t for example o-dichlorobenzene, or nitrobenzene, or if the pigments are subsequently ground with the addition of grindirg auxiliaries.
The term "lower" relating to alkyl radicals includes groups of from 1 to 5, especially 1 to 4, carbon atoms.
The pigments may also be prepared in the presence of a carrier r~.ater~a , for example baryte.
The novel compounds are water-insoluble and insoluble in the common organic solvents and are suitable for 1~L3561~8 pigmenting printing inks, varnished and dispersion ~ paints, for dyeing caoutchouc, plastics and natural ¦ or synthetic resins.
, 5 They are further appropriate for the pigment printing l on substrates, especially textile fiber materials or other flat articles, such as paper.
The pigments may also be used for other fields of application, for example in a finely devided form of the dyeing of rayon of viscose or cellulose ethers or esters, polyamides, polyurethanes, polyglycol terephtha-lates or polyacrylonitriles in the spinning mass, or for the dyeing of paper.
The pigments have a high tinctorial strength and can easily be processed in the mediums mentioned above.
The dyeings have a very good fastness to light and weather and are resistant to the influence of chemicals, especially to solvents.
The following Examples illustrate the invention, the percentages relating to the weight. Temperatures are given in C.
Example 1 10.5 grams of 3-nitro~ aminobenzoic acid ethyl ester are stirred for 1 hour at 10C in a mixture of 80 ml of glacia~l acetic acid and 15 ml of 31 % hydrochloric acid.
Thereafter 10 ml of 5N sodium nitrite solution are rapidly added dropwise, and stirring is continued for 30 minutes i (Disazo solution~. 7.3 g of 1,4-bisaceto-acetylamino-benzene are suspensed in 200 ml of water and dissolved with 5 ml of 33 % sodium hydroxide solution. For coupling the above-menticned d~ Sa70 solution is introduced into a stirring vessel and mixed with 200 ml of ice water and 10 ml of a 10 ~ aqueous solution of oleyl alcohol which h2s been re~cted with 30 mols of ethylene oxide.
Within one hour the alkaline solution of the 1,4-bi~-aceto-acetylamino-benzene is added dropwise, while maintaining the pH at about 3 - 4, with a 5 % aqueous solution of sodium acetate. After finishing the coupling stirring is continued for 30 minutes, the product is suction-filtered and washed with water until salt-free.
The press cake is suspensed in 800 ml of dimethyl formamide and after heating to 130, it is maintained at this temperature for 10 minutes. The pigment is suction-filtered again, washed with dimethyl formami,de, methanol and water and dried. Yield: 17.2 g of an intensely reddish yellow pigment of the formula 1 ' CC2H5 O2N ~ ~
,~
~I3~ H ~ MH ~ ~ CH3 O O
Example 2 l9,G g of 3-nitro-4-aminobenzoic acid methyl ester are stirred in a mix'cure of 160 ml of glacial acetic acid and 30 ml of 30 ~ hydrochloric acid. The reaction mix-ture is cooled to 10 and under the surface of this mixture there is rapidly introduced a solution of 20 ml of 5 :~50W.'_~. nitrite (diazo component.) 1~3~i61~3 j 16 g of 1,4-bisaceto-acetyl-amino-2-methoxy~benzene are dissol~ed in a mixture of 300 ml of' water and ' 10 ml of 33 % sodium hydroxide solution (coupling component). For coupling there are first introduced into a stirring vessel 300 ml of ice water, 30 ml of 2 N-sodium acetate solution, 6 ml of glacial acetic acid and 20 ml of a 10 % aqueous solution of oleyl alcohol which has been reacted with 30 mols of ethylene oxide. At 10~
the solutions of the diazo and the coupling componenet flow within one hour simultaneously to the buffer mixture. After coupling, the product is heated for 30 minutes to 80 and suction-filtered. The pigment is dried at 70, heated for a short time to 110 in 400 ml of N-methylpyrrolidone, suction-filtered, washed with methanol and water and dried. 34.8 g of reddish-yellow pigment with high tinctorial strength of the formula COOC
l COOC~3 2 ~ ~ ~ N02 N
~3C ~ ~ NH ~ NH ~ CH3 O O O O
are obtained.
The following table gives further Examples of disazo compounds which are o~tained by coupling th.e diazotized aromatic amines (diazo component) of the formula II with the coupling componen~ of the formula III:
1 ~356~3 ExampleFormula II Formula III tint ! No. R X Y
____ _ _. __ i 3 CH3 H H reddish-yellow CH3 Cl H ..
CH3 052H5 H orange 10 6 CH3 CH3 H reddish-yellow 7 CH3 Cl Cl yellow 8 CH3 OCH3 OCH3 yellowish-brown 9 CH3 CH3 CH3 orange C2H~ Cl H reddish-yellow 201~ C2H5 CH3 H yellowish~
orange 12 C2H5 OCH3 H orange 13 C2H5 Cl Cl greeni.sh-, yellow 14 C2H5 CH3 CH3 yellowish~
orange C2H5 OCH3 OCH3 yellowish-brown 3016 C2H5 Br H reddish-yellow 17 CH3 OCH3 CH3 orange t 18 n C3H7 H H reddish-yellow 19 n~C4H9 ~ H
il3S6~8 g .
ExampleFormula II Formula III tint No. R X Y
20 CH3 Cl OCH3 yello~ish-orange 21C2~5 C2H5 H reddish-- yello~7 22C2H5 Cl CH3 yello~7
Claims (15)
I claim:
1. A compound of the formula I
wherein R is alkyl of 1 to 4 carbon atoms and X and Y are hydrogen, chlorine, bromine, methyl, ethyl, methoxy or ethoxy.
wherein R is alkyl of 1 to 4 carbon atoms and X and Y are hydrogen, chlorine, bromine, methyl, ethyl, methoxy or ethoxy.
2. A compound as claimed in Claim 1, wherein R is methyl or ethyl.
3. A compound as claimed in Claim 1, wherein X and Y
are hydrogen, chlorine, methyl or methoxy.
are hydrogen, chlorine, methyl or methoxy.
4. The compound as claimed ln Claim 1, wherein R is ethyl and X and Y are hydrogen.
5. The compound as claimed in Claim 1, wherein R is methyl, X is methoxy and Y is hydrogen.
6. The compound as claimed in Claim 1, wherein R is methyl and X and Y are hydrogen.
7. The compound as claimed in Claim 1, wherein R is methyl and X and Y are chlorine.
8. The compound as claimed in Claim 1, wherein R, X
and Y are methyl.
and Y are methyl.
9. The compound as claimed in Claim 1. wherein R is ethyl and X and Y are methyl.
10. The compound as claimed in Claim 1, wherein R is ethyl and X and Y are chlorine.
11. A process for the preparation of a compound as claimed in Claim 1 which comprises diazotizing two molar equivalents of a compound of the ,formula II
II
and coupling onto a compound of the formula III
III
wherein R, X and Y are as defined in Claim 1.
II
and coupling onto a compound of the formula III
III
wherein R, X and Y are as defined in Claim 1.
12. A process as claimed in Claim 11, wherein a mixture of amines of formula II are diazotized.
13. A process as claimed in Claims 11 and 12, wherein the diazotized amine or mixture of amines is coupled onto a mixture of compounds of formula III.
14. A process for pigmenting articles which comprises incorporating into said article a compound as claimed in Claim 1.
15. A process for pigmenting articles which comprises coating said article with a layer containing a compound as claimed in Claim 1.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19792935974 DE2935974A1 (en) | 1979-09-06 | 1979-09-06 | DISAZO CONNECTIONS, METHOD FOR THEIR PRODUCTION AND THEIR USE |
| DEP2935974.8 | 1979-09-06 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1135688A true CA1135688A (en) | 1982-11-16 |
Family
ID=6080167
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000359611A Expired CA1135688A (en) | 1979-09-06 | 1980-09-05 | Disazo compounds, process for their manufacture and their use |
Country Status (5)
| Country | Link |
|---|---|
| EP (1) | EP0025164B1 (en) |
| JP (1) | JPS5649758A (en) |
| CA (1) | CA1135688A (en) |
| DE (2) | DE2935974A1 (en) |
| DK (1) | DK148634C (en) |
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5428136A (en) * | 1992-07-31 | 1995-06-27 | Hoechst Ag | Water-insoluble azo colorants having two azo groups and a 1,4-bis (acetoacetylamino) benzene coupling component |
| US5559216A (en) * | 1992-09-02 | 1996-09-24 | Hoechst Ag | Single-step process for the preparation of bis-(acetoacetylamino) benzene disazo pigments |
| US5616778A (en) * | 1989-12-22 | 1997-04-01 | Sandoz Ltd. | Modified form of bis-1,4-[2'-(2",5"-dimethoxycarbonylphenylazo)-3'-oxobutyramido]benzene and process for its synthesis |
| US5889162A (en) * | 1998-08-10 | 1999-03-30 | Engelhard Corporation | Strong green-shade yellow disazo pigment |
| US6254671B1 (en) | 1999-11-15 | 2001-07-03 | Engelhard Corporation | Very green-shade yellow metallized disazo pigment |
| US6756486B1 (en) | 2003-09-18 | 2004-06-29 | Engelhard Corporation | Non-migrating metallized disazo green shade yellow pigment |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS59228883A (en) * | 1983-06-08 | 1984-12-22 | 松田 巌 | Assembling method of hand drum ornament |
| JP6869720B2 (en) | 2013-06-13 | 2021-05-12 | アンチセンス セラピューティクス リミテッド | Combination therapy |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CH565220A5 (en) * | 1970-02-04 | 1975-08-15 | Sandoz Ag | |
| CH568365A5 (en) * | 1973-03-07 | 1975-10-31 | Ciba Geigy Ag | |
| DE2336915A1 (en) * | 1973-07-20 | 1975-03-13 | Hoechst Ag | NEW DISAZOPIGMENTS AND METHODS OF MANUFACTURING AND USE |
-
1979
- 1979-09-06 DE DE19792935974 patent/DE2935974A1/en not_active Withdrawn
-
1980
- 1980-08-26 EP EP80105050A patent/EP0025164B1/en not_active Expired
- 1980-08-26 DE DE8080105050T patent/DE3062751D1/en not_active Expired
- 1980-09-05 DK DK379480A patent/DK148634C/en not_active IP Right Cessation
- 1980-09-05 JP JP12244080A patent/JPS5649758A/en active Granted
- 1980-09-05 CA CA000359611A patent/CA1135688A/en not_active Expired
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5616778A (en) * | 1989-12-22 | 1997-04-01 | Sandoz Ltd. | Modified form of bis-1,4-[2'-(2",5"-dimethoxycarbonylphenylazo)-3'-oxobutyramido]benzene and process for its synthesis |
| US5428136A (en) * | 1992-07-31 | 1995-06-27 | Hoechst Ag | Water-insoluble azo colorants having two azo groups and a 1,4-bis (acetoacetylamino) benzene coupling component |
| US5559216A (en) * | 1992-09-02 | 1996-09-24 | Hoechst Ag | Single-step process for the preparation of bis-(acetoacetylamino) benzene disazo pigments |
| US5889162A (en) * | 1998-08-10 | 1999-03-30 | Engelhard Corporation | Strong green-shade yellow disazo pigment |
| US6254671B1 (en) | 1999-11-15 | 2001-07-03 | Engelhard Corporation | Very green-shade yellow metallized disazo pigment |
| US6756486B1 (en) | 2003-09-18 | 2004-06-29 | Engelhard Corporation | Non-migrating metallized disazo green shade yellow pigment |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS5649758A (en) | 1981-05-06 |
| DE2935974A1 (en) | 1981-04-09 |
| EP0025164B1 (en) | 1983-04-13 |
| DK148634B (en) | 1985-08-19 |
| DK379480A (en) | 1981-03-07 |
| JPH0147498B2 (en) | 1989-10-13 |
| DK148634C (en) | 1986-01-20 |
| EP0025164A1 (en) | 1981-03-18 |
| DE3062751D1 (en) | 1983-05-19 |
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