US2220598A - Monoazo-dyestuffs insoluble in water - Google Patents
Monoazo-dyestuffs insoluble in water Download PDFInfo
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- US2220598A US2220598A US277017A US27701739A US2220598A US 2220598 A US2220598 A US 2220598A US 277017 A US277017 A US 277017A US 27701739 A US27701739 A US 27701739A US 2220598 A US2220598 A US 2220598A
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- methyl
- phenyl
- pyrazolone
- water
- carbonyl
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- 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
- C09B29/34—Monoazo dyes prepared by diazotising and coupling from other coupling components
- C09B29/36—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds
- C09B29/3604—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds containing only a nitrogen as heteroatom
- C09B29/3647—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds containing only a nitrogen as heteroatom containing a five-membered ring with two nitrogen atoms as heteroatoms
- C09B29/3652—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds containing only a nitrogen as heteroatom containing a five-membered ring with two nitrogen atoms as heteroatoms containing a 1,2-diazoles or hydrogenated 1,2-diazoles
- C09B29/366—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds containing only a nitrogen as heteroatom containing a five-membered ring with two nitrogen atoms as heteroatoms containing a 1,2-diazoles or hydrogenated 1,2-diazoles containing hydroxy-1,2-diazoles, e.g. pyrazolone
Definitions
- the present invention relates to monoaZo-dyestufi's insoluble in water; more particularly it relates to dyestufis of the following general formula:
- Y-O NZ 1 N wherein X represents the group 'CO- or SO2-, R1 and R2 represent alkyl-, -aralkyl-,
- benzeneradical-a stands for methyl, a' carboxlic acid ester group" or phenyl, and Z for a radicalcof the benzene series, and wherein-the benzeneradical-a may be further substituted byalkyl-,' alkoXy-, aryloxygroups or halogen atoms.
- R1 and R2 represent alkyl-,' aralkyl-, aryl' or hydroaromatic radicals which 'may be connected in a heterocyclic ring system,and-wh'erein' the benzene radicala may be further'substituted by alkyl-, alkoxy-, aryloxy-groups orhalogenatoms,
- the new dyestuffs yield vivid yellow and orange tints of good properties'offastness,;especially of goodfastnessto--light; They; are insoluble in water, butvery easilysoluble'in" many bility in organic solvents, p artly'by their considerably better fastness properties; such as higher fastness'to light; the "dyeings produced on rubber by means of the new-dyestuffs bleed during the vulcanisation'process to a considerably small er extent.
- 1 g V p The following examples serve to illustrate the invention, but they are not intended to limit it thereto; the parts are by weight:
- dyestufi formed is filtered with suction, washed well and dried. It dissolves easily in ethyl alcohol, xylene and other organic solvents and colors nitrocellulose lacquers and acetylcellulose lacquers as well as varnishes vivid yellow tints of good fastness to light.
- Example 3 If there are used, in Example 1, instead of 8.7 parts of 1-phenyl-3-methyl-5-pyrazo1one, 11.6 parts of 1-phenyl-5-pyrazolone-3-carboxylic acid ethyl ester, a yellow dyestufi having similar properties is obtained; it colors the various organic solvents and the lacquers prepared by means of these solvents as well as candles and fats yellow tints.
- a yellow dyestuff is prepared, in the manner described in Examples 1 and 2,; from the diazocompound of 11.4 parts of l-amonobenzene-Z- (sulfonyl-diethyl-amine) and 12.2 parts of 1- (2'.5' -dichlorophenyl) -3-methyl 5 pyrazolone. It dissolves easily in organic solvents and colors plastic masses and lacquers prepared by means of these solvents as well as candles and fats greenish yellow tints of good fastness to light.
- a pigment dyestufi is prepared, in the manner described in Example 1,-from the diazo-compound of 9.6 parts of l-aminobenzene-Z-(carbonyl-diethylamine) and 12.8 'parts of 1.3-diphenyl-5-pyrazo1one. It dissolves easily in butyl alcohol, butyl acetate and acetone and colors cellulose ester lacquers, varnishes, candles and fats yellow tints which are more reddish than those obtainable with the dyestufi of Example 1.
- aromatic nuclei of the general formulae appearing in the appended claims do not contain any substituents which are known to render organic compounds soluble in water or alkalies and to tend to depreciate the fastness of the dyestuffs to alkalies.
- substituents of this kind are, for instance, the sulfonic acid and the carboxylic acid group.
- X represents one of the groups CO and SO2--
- R1 and R2 stand for members of the group consisting of alkyl, benzyl, radicals of the benzene and naphthalene series and hydroaromatic radicals, which may be connected to form a heterocyclic ring system
- a1 stands for a member of the group consisting of hydrogen, alkyl, alkoxy, .phenoxy and halogen, and oz for a member of the group consisting of hydrogen and alkyl
- Y stands for a member of the groupconsis-ting of methyl, carboxylic acid ester and phenyl, and Z for a radical of the benzene series, being insoluble-in water, but very easily soluble Since an object of the present invention is toprovide dyestuffs of good fastness properties which dyestuffs are insoluble in water and alka- Diazo-compound irom- Coupled with- Shade 1 l-aminobenzene-Z-(carbonyl-
- alkyl XN ⁇ alkyl N OH wherein X represents one of the groups -CO- and SO2
- a stands for a member of the group consisting of hydrogen, alkyl, alkoxy, phenoxy and halogen
- Y stands for a member of the group consisting of methyl, carboxylic acid ester and phenyl
- Z for a radical of the benzene series, being insoluble in water, but very easily soluble in organic solvents and yielding vivid yellow and orange tints of good properties of fastness, especially of good fastness to light.
- cellulose ester lacquers yellow tints being a yellow powder which dissolves easily in organic solvents, such as acetone, xylene, butyl acetate, butyl alcohol and colors, for instance, cellulose ester lacquers yellow tints.
- organic solvents such as acetone, xylene, butyl acetate, butyl alcohol and colors, for instance, cellulose ester lacquers yellow tints.
- E E l CzHsO 0 0-0 N-CsHE being a yellow powder which dissolves easily in organic solvents, such as acetone, Xylene, butyl acetate, butyl alcohol and colors, for instance, cellulose ester lacquers yellow tints.
Description
Patented Nov. 5, 1940 UNITED STATES PATENT. critics.
MONOAZO-DYESTUFFSINS-OLUBLEIN 7 I I WATER; v r
Ernst Fischer, OiTenbach-on-the-Main, Germany, 1
assignor to General Aniline & Filin' Corporation, a, corporation of Delaware s No Drawing. Application June""2,i 1939, Serial No.2'7'7,017. In Germany June-4,1938
5 Claims.
The present inventionrelates to monoaZo-dyestufi's insoluble in water; more particularly it relates to dyestufis of the following general formula:
Y-O NZ 1 N wherein X represents the group 'CO- or SO2-, R1 and R2 represent alkyl-, -aralkyl-,
arylor-hydroaromatic radicals which-may beconnected to form a heterocylic ring system; Y
stands for methyl, a' carboxlic acid ester group" or phenyl, and Z for a radicalcof the benzene series, and wherein-the benzeneradical-a may be further substituted byalkyl-,' alkoXy-, aryloxygroups or halogen atoms. a
I have found that valuable pigmentdyestuffs may-be obtained by coupling with a 1-aryl-'3= methyI-S-pyrazolone, a '1-aryl 3-aryl-5-pyrazo lone, a 1-aryl-5-pyrazolone3-carboxylic acid estersor a substitution product-thereof the diazocompound from an amine of the general for mula:
Y-XN
where X represents the group CO- or --SOz-, R1 and R2 represent alkyl-,' aralkyl-, aryl' or hydroaromatic radicals which 'may be connected in a heterocyclic ring system,and-wh'erein' the benzene radicala may be further'substituted by alkyl-, alkoxy-, aryloxy-groups orhalogenatoms,
only'such dyestufi components :being used as do* not contain any group lendingsolubility in water, such as the sulfonic or carboxylic acid group.
The new dyestuffs yield vivid yellow and orange tints of good properties'offastness,;especially of goodfastnessto--light; They; are insoluble in water, butvery easilysoluble'in" many bility in organic solvents, p artly'by their considerably better fastness properties; such as higher fastness'to light; the "dyeings produced on rubber by means of the new-dyestuffs bleed during the vulcanisation'process to a considerably small er extent. 1 g V p The following examples serve to illustrate the invention, but they are not intended to limit it thereto; the parts are by weight:
1. 9.6 parts of; lamino=benz'ene-'2-(carbonyl-d1 ethylamine) are diazotized in the usual manner. In order to bind the excess of mineral acid, so dium acetate is added to the diazo-solutionand the whole is then stirred into an aqueous suspen- 1 sion of 8.7 parts of 1-phenyl-3-rnethyl 5-pyrazolone prepared by dissolving this-compound in dilute caustic soda solution andreprecipitating it by means of acetic acid. When the coupling is 'complete,'the-dyestufi formed is filtered with suction, washed Welland dried, It is a yellow 1 powder which easily dissolves in acetone, butyl acetate and Otherbrganicsolvents to a yellowsolution and'colors cellulose ester lacquers vivid and fast tints. The dyestufi corresponds with the 1 [following formula.
'2." 1012f parts of" 1-aminobenz ene-2 (carbonylsolution is made neutral to Congo paper by means of sodium acetate, and then stirred into a suspension of 9.4 parts of 1-(4'-methylpheny1) 3- methyl-5-pyrazolone prepared by dissolving this compound in dilute caustic soda solution and reprecipitating it by means of acetic acid. The
dyestufi formed is filtered with suction, washed well and dried. It dissolves easily in ethyl alcohol, xylene and other organic solvents and colors nitrocellulose lacquers and acetylcellulose lacquers as well as varnishes vivid yellow tints of good fastness to light.
3. If there are used, in Example 1, instead of 8.7 parts of 1-phenyl-3-methyl-5-pyrazo1one, 11.6 parts of 1-phenyl-5-pyrazolone-3-carboxylic acid ethyl ester, a yellow dyestufi having similar properties is obtained; it colors the various organic solvents and the lacquers prepared by means of these solvents as well as candles and fats yellow tints.
4. A yellow dyestuff is prepared, in the manner described in Examples 1 and 2,; from the diazocompound of 11.4 parts of l-amonobenzene-Z- (sulfonyl-diethyl-amine) and 12.2 parts of 1- (2'.5' -dichlorophenyl) -3-methyl 5 pyrazolone. It dissolves easily in organic solvents and colors plastic masses and lacquers prepared by means of these solvents as well as candles and fats greenish yellow tints of good fastness to light.
5. A pigment dyestufi is prepared, in the manner described in Example 1,-from the diazo-compound of 9.6 parts of l-aminobenzene-Z-(carbonyl-diethylamine) and 12.8 'parts of 1.3-diphenyl-5-pyrazo1one. It dissolves easily in butyl alcohol, butyl acetate and acetone and colors cellulose ester lacquers, varnishes, candles and fats yellow tints which are more reddish than those obtainable with the dyestufi of Example 1.
The following table illustrates a number of other mono-azo-dyestufis obtainable by the pres- "ent invention which are likewise easily soluble in solvents usually applied for these purposes an have good properties of iastness.
lies, it is to be understood that the aromatic nuclei of the general formulae appearing in the appended claims do not contain any substituents which are known to render organic compounds soluble in water or alkalies and to tend to depreciate the fastness of the dyestuffs to alkalies. Substituents of this kind are, for instance, the sulfonic acid and the carboxylic acid group.
I claim:
1. The water-insoluble monoazo-dyestufl's of the following general formula:
wherein X represents one of the groups CO and SO2--, R1 and R2 stand for members of the group consisting of alkyl, benzyl, radicals of the benzene and naphthalene series and hydroaromatic radicals, which may be connected to form a heterocyclic ring system; a1 stands for a member of the group consisting of hydrogen, alkyl, alkoxy, .phenoxy and halogen, and oz for a member of the group consisting of hydrogen and alkyl; Y stands for a member of the groupconsis-ting of methyl, carboxylic acid ester and phenyl, and Z for a radical of the benzene series, being insoluble-in water, but very easily soluble Since an object of the present invention is toprovide dyestuffs of good fastness properties which dyestuffs are insoluble in water and alka- Diazo-compound irom- Coupled with- Shade 1 l-aminobenzene-Z-(carbonyl-N-ethyl-cyclohexylamine) 1-(4'-methylphenyl)-3-methyl-5-pyrazolone .Yellow 2 l-amm?benzene-2-(sulfony1-N-(n)-butyl-[2-methyl]-phenyla- 1-(2- methylphenyl)-3-methy1-5-pyrazolone Do.
mine 3 do 1-(2.5-dich1oropheny1)-3-methyl5-pyrazo1one Do. 4 1-ammobenzeue-2-(su1fonyl-d1benzy1amme) 1-(2-ch1orophenyl)-3-methyl-5-pyrazolone Do. 5 1-aminobenzene-2-sulfonyl-N-bepzyl-cyclohexylamine) l-phenyl-Ii-methyl-fi-pyrazolone D0. 6 l-ami nobenzene-2- carbonyl-N-plpendlne) 1-phenyl-fi-pyrazolone-3-carboxylic acid ethyl ester Do. 7 1-ammo-3-methylbeuzene-6-(carbonyl-dlmethylamlne) l-phenyl-3-methyl-apyrazolone Do. 8 l-aminO-B-methyIbenZene-G-(carbonyl-N-benzylphenylamine) dn Do. 9 l-amino-E-methylbcnzene-S-(carbonyl-dicyclo-hexylamine) do D 10 l-amino-Ii-methylbenzene-d(carbonyl-diphenylamine) Do, 11 l-amin)-4-chlor0benzene-6-(carbonyl-N-phenyl-2'-naphthyl- D amine 12 l-aminoi-chlorobenzene-6-(carbonyl-N-carbazole) do D 13 l-amino i-phenoxybenzene-G-(carbonyl-N-methyl-benzylamine). l-(4-methyl-phenyl)-3-methyl-5-pyrazolone Do. 14 1-aminol-methoxybenzene-6-(sulfonyl-n-dibutylamine) D0. 15 l-amino-4-ethoxybenzene-6-(sulfonyl-diethylamine) 1-(4'-chloro-phenyl)-3-methyl-5-pyrazolone Do. 16 l-amino33-methyl-4-chlorobenzene-6-(sulfonyl-N-methyl-phenyldn Do, l amine 17 1-aminobenzene-2-(carbonyl-dibenzylamine) 1- henyl--pyrazolone-S-carboxylic acid ethyl ester Do. 18 i-aminobenzene-2-(carbonyl-N-ethyl-cyc1ohexylamine) l- 3'-nitropheny1)-3-methy1-5-pyrazolone Do. 19 1-amino-s-methoxybenzene-fi-(carbonyl-nfdibutylamine) 1-phenyl-3-methyl-5-pyrazolone Do. 20 l-amino-8-methoxybenzene-6- (carbonyl-drethylamine) dn D 21 n v l-phenyl-5- yrezolone-3-carboxylic acid ethyl est Do. 22 d0 l-22-ch1oro -phenyl-B-methyl-S-pyrazolone Do. 23 do i 1- 2.5'-dichloro)-phenyl-3-methy1-5-pyrazolone. Do. 24 i-amino-Zi-ethoxybenzene-fi-(carbonyl-dlethylamme) do D 25 i-zminobenzene-Z-(sulfonyl-dimethylamine) 1-(2-methyl-6-ch1oro)-phenyl-3-methyl-6-pyrazolono Do. 26 l-agiiilio-s-methylbenzene-fi-(carbonyl-N-phenyl-2'-naphl-phenyl-a-methyl-fi-pyrazolone Do.
t y amlne. V 1 27 1-amino-i-chlorobenzene-fi-(carbonyl-N-methyl-benzylamine) I Do, 28 1-amino-3-methyl-4-chlorobenzene-6-(sulfonyl-n-dibutylamine) do Do. 29 1-aminobenzene-2-(sulfonyl-dlmethylamine) 1-(2-chloro)-phenyl-3-methyI-5-pyrazolone; Do.
pecially of good fastness to light,
2. The water-insoluble monoazo-dyestuffs of the following general formula:
alkyl XN\ alkyl N OH wherein X represents one of the groups -CO- and SO2, a stands for a member of the group consisting of hydrogen, alkyl, alkoxy, phenoxy and halogen, Y stands for a member of the group consisting of methyl, carboxylic acid ester and phenyl, and Z for a radical of the benzene series, being insoluble in water, but very easily soluble in organic solvents and yielding vivid yellow and orange tints of good properties of fastness, especially of good fastness to light.
3. The water-insoluble monoazo-dyestufi of the following formula:
being a yellow powder which dissolves easily in organic solvents, such as acetone, xylene, butyl acetate, butyl alcohol and colors, for instance, cellulose ester lacquers yellow tints.
4. The water-insoluble monoazo-dyestuff of the following formula:
CzHs
C ON
- CzH5 t E E l CzHsO 0 0-0 N-CsHE being a yellow powder which dissolves easily in organic solvents, such as acetone, Xylene, butyl acetate, butyl alcohol and colors, for instance, cellulose ester lacquers yellow tints.
ERNST FISCHER.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2220598X | 1938-06-04 |
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| Publication Number | Publication Date |
|---|---|
| US2220598A true US2220598A (en) | 1940-11-05 |
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| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US277017A Expired - Lifetime US2220598A (en) | 1938-06-04 | 1939-06-02 | Monoazo-dyestuffs insoluble in water |
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Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2898178A (en) * | 1955-09-27 | 1959-08-04 | Bayer Ag | Process of dyeing polyester materials |
| US3234207A (en) * | 1962-05-29 | 1966-02-08 | Hoechst Ag | Water-soluble yellow monoazo-dyestuffs and process for preparing them |
| US4055557A (en) * | 1972-08-12 | 1977-10-25 | Bayer Aktiengesellschaft | Sulfonamidobenzene-azo-aminopyrazole dyestuffs |
| US4594411A (en) * | 1981-08-24 | 1986-06-10 | Basf Aktiengesellschaft | Sulfonated monoazo colorant lake obtained by di-azo coupling of 5-acetylamino-2-aminobenzene-1-sulfonic acid with 1-(3'-sulfophenyl)-3-methylphyrazol-5-one |
| US4965345A (en) * | 1986-10-09 | 1990-10-23 | Basf Aktiengesellschaft | Solvent azo dyes having carboxylic acid functions |
-
1939
- 1939-06-02 US US277017A patent/US2220598A/en not_active Expired - Lifetime
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2898178A (en) * | 1955-09-27 | 1959-08-04 | Bayer Ag | Process of dyeing polyester materials |
| US3234207A (en) * | 1962-05-29 | 1966-02-08 | Hoechst Ag | Water-soluble yellow monoazo-dyestuffs and process for preparing them |
| US4055557A (en) * | 1972-08-12 | 1977-10-25 | Bayer Aktiengesellschaft | Sulfonamidobenzene-azo-aminopyrazole dyestuffs |
| US4594411A (en) * | 1981-08-24 | 1986-06-10 | Basf Aktiengesellschaft | Sulfonated monoazo colorant lake obtained by di-azo coupling of 5-acetylamino-2-aminobenzene-1-sulfonic acid with 1-(3'-sulfophenyl)-3-methylphyrazol-5-one |
| US4965345A (en) * | 1986-10-09 | 1990-10-23 | Basf Aktiengesellschaft | Solvent azo dyes having carboxylic acid functions |
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