CA1128501A - Azo dyes - Google Patents
Azo dyesInfo
- Publication number
- CA1128501A CA1128501A CA354,040A CA354040A CA1128501A CA 1128501 A CA1128501 A CA 1128501A CA 354040 A CA354040 A CA 354040A CA 1128501 A CA1128501 A CA 1128501A
- Authority
- CA
- Canada
- Prior art keywords
- weak
- compound
- medium
- formula
- modification
- 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
- 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
- C09B67/0001—Post-treatment of organic pigments or dyes
- C09B67/0014—Influencing the physical properties by treatment with a liquid, e.g. solvents
- C09B67/0015—Influencing the physical properties by treatment with a liquid, e.g. solvents of azoic 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
- 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
- C09B29/3617—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds containing only a nitrogen as heteroatom containing a six-membered heterocyclic with only one nitrogen as heteroatom
- C09B29/3621—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds containing only a nitrogen as heteroatom containing a six-membered heterocyclic with only one nitrogen as heteroatom from a pyridine ring
- C09B29/3626—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds containing only a nitrogen as heteroatom containing a six-membered heterocyclic with only one nitrogen as heteroatom from a pyridine ring from a pyridine ring containing one or more hydroxyl groups (or = O)
- C09B29/363—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds containing only a nitrogen as heteroatom containing a six-membered heterocyclic with only one nitrogen as heteroatom from a pyridine ring from a pyridine ring containing one or more hydroxyl groups (or = O) from diazotized amino carbocyclic rings
-
- 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
- C09B67/0025—Crystal modifications; Special X-ray patterns
- C09B67/0028—Crystal modifications; Special X-ray patterns of azo compounds
- C09B67/0029—Crystal modifications; Special X-ray patterns of azo compounds of monoazo compounds
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Coloring (AREA)
- Pyridine Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
Abstract of the Disclosure The present invention relates to a compound of formula I
Description
~^ ~
~l28S~
C~e 150-~1319 I~IPROVEMENTS IN OR_REL*TING T~ ORCANIC CO.~IPOUNDS
The present in~ention relates to pyrldone dispex~e ~
dye~tuffs. .
More partlcularly, the present inventlon provide~
a compound of formula I
C6H5~CH2-O-CO ~ ~ ~ N ~ ~I~
OH [C 2)3 3 .
Th~ compound of formula I exists in 4 diff~re~t ~rystal modlflcations.
When dlazotized Dara-amino benzoic acld benzyl ester is coupled with 1-n-butyl-3-cyano-4-methyl-6-hydroxy-pyridone-2 in accordance with known methods, preferably ln aqueous medlum having a p~l of from 3-6 at 0-10C, th~
a-modlflcatlon is obtalned. The ~-modificatlon may be obtained by recrystallizlng the dried ~-modificatlon from 2-ethoxyethanol.
The ~ -modlficat~on may b~ obtained by heating an ~queous suspenslon of the ~-modification whlch has been :
.~ ' ~ S~ ~ 150-4319 adjusted to a pH between 2 and 4 for t to 5 hour~ at temperatures between 80 and 100 C . Preferably a cold suspension of the dye is adjusted to p~ 3 and is heat~d at temperatures of rom 90 to ~5C i-or approximately 2 hours. In addition the suspenslon sultably contains an anionic suxface active agent. The suspension may be formed with the dried and isolated ~-modification or may be formed with the moist presscake or alternatively the unfiltered coupling suspension may be employed thus avoiding the separation and isolation steps.
The ~-modification can also be obtalned by repe~ted recrystallization of pure dry ~-modlflcatlon from 2-methoxy- or 2-ethoxyethanol.
The J-modificatlon may be obtalned by heatlng an aqueous suspen~lon of any of the other crystal forms at approximately 130C in an autoclave. Heatlng may be effected for from one to 4 hours~ Here again the suspenston sultably contalns an anlonlc surface active agen~. Once the J form has been obtained lt i~ advantageous to seed the suspen~ion before the heat treatment for further productlon.
The four modlflcatlons of the compound of formula I
may be distinguished by thelr X-ray dlffractlon spectra.
Table 1 shows the lnterplanar spacing ~d-values) in Angstrom unlts of the observed lines ln the X-ray dlffractlon spectrum as measured by a Gulnier/De Wolff ~Z~35Q~
~ 50-43 19 .
camera uslng Cu~ radiation. The intensity II~ of the lines was e~t~mated on a 4 step s.-ale: ~crong l~3), med~um ~m) t weak lw) vexy weak ~vw~ . A dllffuse line 1~ indicated by the letter d.
s~
T A B L E
, - modifi~ation ~~modification Line Nod~value I Line No . d ~a3ue 16,8 ~ 1 8,6wd 214,0 w 2 8,0vwd 3ll,S v~ 3 7,4wd 410,0 m 4 S,6wd 8,0 vw 5 4,5 w 6 7,55 vw 6 4,3vwd 7 7,0 w 7 3,9vwd 8 6,8 w 8 ~ 3,6vwd 9 5,99 vw 9 3,38vwd 10 S,8 vw lO 3,15 vwd 11 S,7 ~w 11 2,6vwd 12 5,4 ~rw 135,35 v~
144, 75 vw ~:
154, 35 vw 16 4J2 v~
17 4,0 ~7w 183,95 vw 193,85 ~w 203,48 213,38 m 223,29 m 233, lg vw 243,09 vw 252 ~ 25 v~
' ~
' :'
~l28S~
C~e 150-~1319 I~IPROVEMENTS IN OR_REL*TING T~ ORCANIC CO.~IPOUNDS
The present in~ention relates to pyrldone dispex~e ~
dye~tuffs. .
More partlcularly, the present inventlon provide~
a compound of formula I
C6H5~CH2-O-CO ~ ~ ~ N ~ ~I~
OH [C 2)3 3 .
Th~ compound of formula I exists in 4 diff~re~t ~rystal modlflcations.
When dlazotized Dara-amino benzoic acld benzyl ester is coupled with 1-n-butyl-3-cyano-4-methyl-6-hydroxy-pyridone-2 in accordance with known methods, preferably ln aqueous medlum having a p~l of from 3-6 at 0-10C, th~
a-modlflcatlon is obtalned. The ~-modificatlon may be obtained by recrystallizlng the dried ~-modificatlon from 2-ethoxyethanol.
The ~ -modlficat~on may b~ obtained by heating an ~queous suspenslon of the ~-modification whlch has been :
.~ ' ~ S~ ~ 150-4319 adjusted to a pH between 2 and 4 for t to 5 hour~ at temperatures between 80 and 100 C . Preferably a cold suspension of the dye is adjusted to p~ 3 and is heat~d at temperatures of rom 90 to ~5C i-or approximately 2 hours. In addition the suspenslon sultably contains an anionic suxface active agent. The suspension may be formed with the dried and isolated ~-modification or may be formed with the moist presscake or alternatively the unfiltered coupling suspension may be employed thus avoiding the separation and isolation steps.
The ~-modification can also be obtalned by repe~ted recrystallization of pure dry ~-modlflcatlon from 2-methoxy- or 2-ethoxyethanol.
The J-modificatlon may be obtalned by heatlng an aqueous suspen~lon of any of the other crystal forms at approximately 130C in an autoclave. Heatlng may be effected for from one to 4 hours~ Here again the suspenston sultably contalns an anlonlc surface active agen~. Once the J form has been obtained lt i~ advantageous to seed the suspen~ion before the heat treatment for further productlon.
The four modlflcatlons of the compound of formula I
may be distinguished by thelr X-ray dlffractlon spectra.
Table 1 shows the lnterplanar spacing ~d-values) in Angstrom unlts of the observed lines ln the X-ray dlffractlon spectrum as measured by a Gulnier/De Wolff ~Z~35Q~
~ 50-43 19 .
camera uslng Cu~ radiation. The intensity II~ of the lines was e~t~mated on a 4 step s.-ale: ~crong l~3), med~um ~m) t weak lw) vexy weak ~vw~ . A dllffuse line 1~ indicated by the letter d.
s~
T A B L E
, - modifi~ation ~~modification Line Nod~value I Line No . d ~a3ue 16,8 ~ 1 8,6wd 214,0 w 2 8,0vwd 3ll,S v~ 3 7,4wd 410,0 m 4 S,6wd 8,0 vw 5 4,5 w 6 7,55 vw 6 4,3vwd 7 7,0 w 7 3,9vwd 8 6,8 w 8 ~ 3,6vwd 9 5,99 vw 9 3,38vwd 10 S,8 vw lO 3,15 vwd 11 S,7 ~w 11 2,6vwd 12 5,4 ~rw 135,35 v~
144, 75 vw ~:
154, 35 vw 16 4J2 v~
17 4,0 ~7w 183,95 vw 193,85 ~w 203,48 213,38 m 223,29 m 233, lg vw 243,09 vw 252 ~ 25 v~
' ~
' :'
2~
. 150-431 Ta~le 1 contin;ued ~ modi-Fica~ion S- ~odification Line No d~value Lin~ ~0 d (Aa) ue 1 16,5 vw 1 14~1 m 2 11,5 w 2 11,5 vw
. 150-431 Ta~le 1 contin;ued ~ modi-Fica~ion S- ~odification Line No d~value Lin~ ~0 d (Aa) ue 1 16,5 vw 1 14~1 m 2 11,5 w 2 11,5 vw
3 10,6 w 3 10,3 YW
4 8,4 vw 4 8,2 m ~,0 w 5 7,~
6. 7~5 w 6 7,2 w 7 5,65 vw 7 5,08 w 8 5,48 m 8 4,9 ~
9 5,43 m 9 4,5 vw 4,9g vw 10 4,25 vw 11 4,8 w 11 3,69 m 12 4,62 w 12 3,48 w 13 4,4S w 13 3,4 m 14 4,21 vw 14 3,19 w ~,13 vw 15 3,14 vw 16 4,09; vw 16 3,1 w 17 3,92 vw ` 18 3,63 vw 19 3,55 vw 3,4 ~ ~
21 3,18 m 22 2,94 w 23 2,9 w 2~ . 2,78 . vw 25. 2,73 vw 26 2,48 vw ~7 2~23 vw 28 2>18 vw 29 1 ~ 873 wd
6. 7~5 w 6 7,2 w 7 5,65 vw 7 5,08 w 8 5,48 m 8 4,9 ~
9 5,43 m 9 4,5 vw 4,9g vw 10 4,25 vw 11 4,8 w 11 3,69 m 12 4,62 w 12 3,48 w 13 4,4S w 13 3,4 m 14 4,21 vw 14 3,19 w ~,13 vw 15 3,14 vw 16 4,09; vw 16 3,1 w 17 3,92 vw ` 18 3,63 vw 19 3,55 vw 3,4 ~ ~
21 3,18 m 22 2,94 w 23 2,9 w 2~ . 2,78 . vw 25. 2,73 vw 26 2,48 vw ~7 2~23 vw 28 2>18 vw 29 1 ~ 873 wd
- 5 -~8~
The compound of formula I is useful for dyeing and printing synthetic or semi-synthetic high moleaular weight, hydrophobic organic substrates from aqueous suspension~
The preferred substrates are those consisting of or comprising linear, aromatic polyesters, cellulose 21J2 ac~tate,cellulose triacetate and synthetic polyamides. The substrate may be in loose fibre,yarn o:r fabric form. For dyeing the dyestuff is made up into dyeing preparations in accordance with known methods e.g. grinding in the presence of dispersing agents etc. Dyeing and printing may be carried out in accordance with known methods. However, the ~- and ~-modifications are unsuitable for dyeing at high temperatures, e.g. temperatures of over 100C, under pressure as they have a tendency to form large crystals under these conditions, therefore when the dyestuff ls to be employed for high-temperature dyeings the ~- and ~-modiflcations should be converted to the ~ - and/or ~ -modifications or alter-natively they should be admixed with at least 10 times their welght of the stable ~ - and ~ -modifications. The dyestuff of the invention, especially the ~ and ~-modific-ations, has good resistance to hydrolysis and good build-up--power on the above-mentioned substrates and gives dyeings having notable fastnesses, in particular light-, wet- (e.g.
sweat-, water- and wash-),thermofixation- and sublimation-fastness and fastness to solvents and dry-rubbing.
The following Examples further serve to illustrate the invention. In the Examples all parts are by weight and the temperatures are in degrees Centigrade.
~- - 6 -,, ~ ~Z85~
Example t 1~.2~ Parts ~-aminobenzoic acid benzylester /97% pure~
are dissolved in 70 parts glacial acetic at 50 and reacted with 20 parts conc, hydrochloric acid, 40 parts ice and a further 20 parts conc. hydrochloric acid. At 4-6~ the fine crystal suspension is quickly reacted with 22 parts 4N-sodium nitrite solution. The mixture is stirred for 10 minutes at 10-12 and ~hen cooled to 0-5 with ice. The excess nitrite is destroyed with amldosulphonic acid and the solution is filtered clear.
A solution of 16.2 parts 1-n-butyl-3-cyano-6-hydroxy 4-methylpyridone-2 in 200 parts water at pH 5 to 7 at 0 to 5 is reacted, with stirring, for 1 hour with the diazo solution whereby the pH and the temperature are maintained constant by the addition of aqueous sodium hydroxide and ice, respectively. A small excess of di-azonium compound remains, the mixture is stirred over-night whereupon the suspension reaches room temperature and the excess diazonium compound disappears. After filtering, washing and drying at ~0 in vacuo good yields of pure dyestuff are obtained. The dyestuff obtained is in the ~-crystal modificatlon form.
Example 2 Pre~aration of the ~-modification ___ ______________ _____________ 10 gms. of the dyestuff prepared as described in Example 1 either in dried form or as a moist presscake are made into a thin paste by stirring with water~ 1 gm , ............................ .
~ 150-4319 of a surface active agent (e.gO sodium dinaphthylmetXane disulphonateJ is added, the pH is adjusted to 3 with hydrochloric acid and the mixture is heated to 85-9S
for ~ hours. After filtering, washing and drying the ~-modification of the dyestuff is obtained.
Th~ unfiltered coupling suspension of the dyestuf may also be subjected to the above heat treatment in order to obtain the stable ~-modification.
The stable ~-modification may also be obtained by repeated recrystallization of the dried dyestuff from methyl- or ethylglycol.
Example 3 Pre2aration of the J modification .___ _______ ______________________ 10 Parts of the dyestuff obtained as described in Example 1 either dried or in the moist presscake are made into a thin paste with water. 1 part of an anionic surface active agent (e.g. sodium dinaphthylmethanedisulphonate~
are added thereto and the mixture is heated in an auto-clave to a temperature of 130 to 132 for 2 hoursO After cooling, filtering, wafihing and Arying the ~-modification is obtained The unfiltered coupling suspension of the dye of Example 1 may also be used and subjected to the heat treatment described above.
Dyeinq Example A
The stable modification of Example 2 or 3 is ground in the presence of a dispersing agent, e.g. lignin-~1~8S~
15~-4319 sulphonate and spray dried to obtain a dye preparation having a particle si~e of less than or equal to 1 ~, the blend containing 3 parts dye and 7 parts dispersing agenta 10 Parts of the finely dispersed dyestuff oreparation is added to 1000 parts water and the whole is added at 60 to a circulating bath containing 13000 parts of which 30 parts are ammonium sulphate, 0,3 paxts formic acid and the rest is water. Prewashed cross-wound spool (1000 parts polyester yarn) is put in the bathO The autoclave is closed and heated from 60 to 130 over 35 minutes.
After 15 minutes at 130 the autoclave is cooled to 80~, the dyebath i.s run-off and the dyed substrate is washed thoroughly with cold water. Subsequently, the substrate is subjected to spinning and dried in a drying cabinet.
A deep (approx. ~wice standard depth), level dyeing of a greenish yellow shade free from undissolved particles on the surface having good wet and rubbing fastnesses is obtainedO The dyeing apparatus is also free from deposits of dyèstuff and can be employed as such for the next dyeing. The waste water is practically colourless indicating good build-up of the dyestuff.
Dyeing Example B
7 Parts of the dyestuff prepared as de~cribed in Example 1 are ground with 4 parts sodium dinaphthylmethan-disulphonate, 4 parts sodium cetyl sulphate and 5 parts anhydrous sodium sulphate in a ball mill for 48 hours.
_ g _ 1 Part of the dyestuff preparation is made into a paste wlth water and the suspension ls added through a si~ve to a dyebath containing 1:2 parts sodium sulphoric^
lnoleate (80% sulphonated~ and 8 parts anhydrous ammonium sulphate in 4000 parts water.
The dyebath is adjusted to pH 5 with formic acid.
100 parts polyester fibre are added to the bath at room temperature and the dyebath i5 heated to 98C over 30 minutes (12 parts ortho-phenylphenol carrier are added at 60) and the substrate is dyed for 2 hours at this temperature. The greenish-yellow dyed fibre is washed, soaped, washed again and dried. An even dyeing with good fastnesses is obtained.
'
The compound of formula I is useful for dyeing and printing synthetic or semi-synthetic high moleaular weight, hydrophobic organic substrates from aqueous suspension~
The preferred substrates are those consisting of or comprising linear, aromatic polyesters, cellulose 21J2 ac~tate,cellulose triacetate and synthetic polyamides. The substrate may be in loose fibre,yarn o:r fabric form. For dyeing the dyestuff is made up into dyeing preparations in accordance with known methods e.g. grinding in the presence of dispersing agents etc. Dyeing and printing may be carried out in accordance with known methods. However, the ~- and ~-modifications are unsuitable for dyeing at high temperatures, e.g. temperatures of over 100C, under pressure as they have a tendency to form large crystals under these conditions, therefore when the dyestuff ls to be employed for high-temperature dyeings the ~- and ~-modiflcations should be converted to the ~ - and/or ~ -modifications or alter-natively they should be admixed with at least 10 times their welght of the stable ~ - and ~ -modifications. The dyestuff of the invention, especially the ~ and ~-modific-ations, has good resistance to hydrolysis and good build-up--power on the above-mentioned substrates and gives dyeings having notable fastnesses, in particular light-, wet- (e.g.
sweat-, water- and wash-),thermofixation- and sublimation-fastness and fastness to solvents and dry-rubbing.
The following Examples further serve to illustrate the invention. In the Examples all parts are by weight and the temperatures are in degrees Centigrade.
~- - 6 -,, ~ ~Z85~
Example t 1~.2~ Parts ~-aminobenzoic acid benzylester /97% pure~
are dissolved in 70 parts glacial acetic at 50 and reacted with 20 parts conc, hydrochloric acid, 40 parts ice and a further 20 parts conc. hydrochloric acid. At 4-6~ the fine crystal suspension is quickly reacted with 22 parts 4N-sodium nitrite solution. The mixture is stirred for 10 minutes at 10-12 and ~hen cooled to 0-5 with ice. The excess nitrite is destroyed with amldosulphonic acid and the solution is filtered clear.
A solution of 16.2 parts 1-n-butyl-3-cyano-6-hydroxy 4-methylpyridone-2 in 200 parts water at pH 5 to 7 at 0 to 5 is reacted, with stirring, for 1 hour with the diazo solution whereby the pH and the temperature are maintained constant by the addition of aqueous sodium hydroxide and ice, respectively. A small excess of di-azonium compound remains, the mixture is stirred over-night whereupon the suspension reaches room temperature and the excess diazonium compound disappears. After filtering, washing and drying at ~0 in vacuo good yields of pure dyestuff are obtained. The dyestuff obtained is in the ~-crystal modificatlon form.
Example 2 Pre~aration of the ~-modification ___ ______________ _____________ 10 gms. of the dyestuff prepared as described in Example 1 either in dried form or as a moist presscake are made into a thin paste by stirring with water~ 1 gm , ............................ .
~ 150-4319 of a surface active agent (e.gO sodium dinaphthylmetXane disulphonateJ is added, the pH is adjusted to 3 with hydrochloric acid and the mixture is heated to 85-9S
for ~ hours. After filtering, washing and drying the ~-modification of the dyestuff is obtained.
Th~ unfiltered coupling suspension of the dyestuf may also be subjected to the above heat treatment in order to obtain the stable ~-modification.
The stable ~-modification may also be obtained by repeated recrystallization of the dried dyestuff from methyl- or ethylglycol.
Example 3 Pre2aration of the J modification .___ _______ ______________________ 10 Parts of the dyestuff obtained as described in Example 1 either dried or in the moist presscake are made into a thin paste with water. 1 part of an anionic surface active agent (e.g. sodium dinaphthylmethanedisulphonate~
are added thereto and the mixture is heated in an auto-clave to a temperature of 130 to 132 for 2 hoursO After cooling, filtering, wafihing and Arying the ~-modification is obtained The unfiltered coupling suspension of the dye of Example 1 may also be used and subjected to the heat treatment described above.
Dyeinq Example A
The stable modification of Example 2 or 3 is ground in the presence of a dispersing agent, e.g. lignin-~1~8S~
15~-4319 sulphonate and spray dried to obtain a dye preparation having a particle si~e of less than or equal to 1 ~, the blend containing 3 parts dye and 7 parts dispersing agenta 10 Parts of the finely dispersed dyestuff oreparation is added to 1000 parts water and the whole is added at 60 to a circulating bath containing 13000 parts of which 30 parts are ammonium sulphate, 0,3 paxts formic acid and the rest is water. Prewashed cross-wound spool (1000 parts polyester yarn) is put in the bathO The autoclave is closed and heated from 60 to 130 over 35 minutes.
After 15 minutes at 130 the autoclave is cooled to 80~, the dyebath i.s run-off and the dyed substrate is washed thoroughly with cold water. Subsequently, the substrate is subjected to spinning and dried in a drying cabinet.
A deep (approx. ~wice standard depth), level dyeing of a greenish yellow shade free from undissolved particles on the surface having good wet and rubbing fastnesses is obtainedO The dyeing apparatus is also free from deposits of dyèstuff and can be employed as such for the next dyeing. The waste water is practically colourless indicating good build-up of the dyestuff.
Dyeing Example B
7 Parts of the dyestuff prepared as de~cribed in Example 1 are ground with 4 parts sodium dinaphthylmethan-disulphonate, 4 parts sodium cetyl sulphate and 5 parts anhydrous sodium sulphate in a ball mill for 48 hours.
_ g _ 1 Part of the dyestuff preparation is made into a paste wlth water and the suspension ls added through a si~ve to a dyebath containing 1:2 parts sodium sulphoric^
lnoleate (80% sulphonated~ and 8 parts anhydrous ammonium sulphate in 4000 parts water.
The dyebath is adjusted to pH 5 with formic acid.
100 parts polyester fibre are added to the bath at room temperature and the dyebath i5 heated to 98C over 30 minutes (12 parts ortho-phenylphenol carrier are added at 60) and the substrate is dyed for 2 hours at this temperature. The greenish-yellow dyed fibre is washed, soaped, washed again and dried. An even dyeing with good fastnesses is obtained.
'
Claims (7)
PROPERTY OR PRIVILEGE IS CLAIMED ARE DEFINED AS FOLLOWS:
1. The compound of formula I, (I)
2. The ?-modification of the compound of formula I, according to Claim 1, having the X-ray diffraction spectra (Cu-K.alpha.1-radiation) exhibiting lines at d-values of 11.5 (weak), 10.6 (weak), 8.0 (weak), 7.5 (weak), 5.48 (medium), 5.43 (medium), 4,8 (weak), 4.62 (weak), 4,45 (weak), 3,4 (strong), 3.18 (medium), 2.94 (weak) and 2,9 (weak) Angstrom.
3. The ?-modification of the compound of formula I, according to Claim 1, having the X-ray diffraction spectra (Cu-K.alpha.1-radiation) exhibiting lines at d-values of 14.1 (medium), 8.2 (medium), 7.8 (medium), 7.2 (weak), 5.08 (weak), 3,69 (medium), 3.48 (weak), 3.4 (medium), 3.19 (weak) and 3.1 (weak) Angstrom.
4. A process for the preparation of a compound of formula I, as defined in Claim 1, comprising coupling diazotized para-aminobenzoic acid benzyl ester with 1-n-butyl-3-cyano-4-methyl-6-hydroxypyridone-2.
5. A process for the preparation of the ?-modification of the compound of formula I, as defined in Claim 2, comprising treating an aqueous paste of the compound of formula I, whenever produced by a process according to Claim 4, having a pH of from 2 to 4 at temperatures of from 80 to 100°C.
6. A process for the preparation of the ?-modification of the compound of formula I, as defined in Claim 3, comprising heating the .alpha.-, .beta.-, or ?-modific-ation of the compound of formula I in an aqueous medium to a temperature of at least 130°C under pressure.
7. A process for dyeing or printing substrates consisting of or comprising synthetic or semi-synthetic high molecular weight, hydrophobic organic substrates comprising employing a compound according to Claim 1 2, or 3 as dyeing or printing agent.
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH5671/79 | 1979-06-18 | ||
| CH567179A CH642095A5 (en) | 1979-06-18 | 1979-06-18 | Azo compounds |
| CH919379A CH650522A5 (en) | 1979-10-11 | 1979-10-11 | Dyeing-stable modification of an azo dye |
| CH9193/79 | 1979-10-11 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1128501A true CA1128501A (en) | 1982-07-27 |
Family
ID=25698182
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA354,040A Expired CA1128501A (en) | 1979-06-18 | 1980-06-16 | Azo dyes |
Country Status (11)
| Country | Link |
|---|---|
| AT (1) | AT382632B (en) |
| BR (1) | BR8003764A (en) |
| CA (1) | CA1128501A (en) |
| DD (1) | DD151953A5 (en) |
| DE (1) | DE3021555A1 (en) |
| ES (1) | ES8105367A1 (en) |
| FR (1) | FR2459269B1 (en) |
| GB (1) | GB2054632B (en) |
| HK (1) | HK31784A (en) |
| IT (1) | IT1128162B (en) |
| YU (1) | YU42510B (en) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3125159A1 (en) * | 1981-06-26 | 1983-01-13 | Cassella Ag, 6000 Frankfurt | COLORABLE STABLE MODIFICATION OF A DISPERSION DYE, METHOD FOR THEIR PRODUCTION AND USE |
| US4453944A (en) * | 1982-04-07 | 1984-06-12 | Ciba-Geigy Corporation | Dye stable to dyeing, processes for producing it, and its use for dyeing and printing synthetic and semi-synthetic fibre materials |
| DE4000529A1 (en) * | 1990-01-10 | 1991-07-11 | Cassella Ag | FAERBESTABILE SS MODIFICATION OF A MONOAZO DYE, PROCESS FOR THEIR PRODUCTION AND THEIR USE |
| CN106675083A (en) * | 2016-12-16 | 2017-05-17 | 江苏道博化工有限公司 | Synthetic method for disperse yellow 231 |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4140684A (en) * | 1968-05-15 | 1979-02-20 | Fidelity Union Trust Company, Executive Trustee Under The Sandoz Trust | Azo dyes having a 6-hydroxy-pyridone-2 coupling component radical having a substituent in the 1-position |
| CH503781A (en) * | 1968-05-15 | 1971-02-28 | Sandoz Ag | Process for the production of basic dyes |
| DE1917278B2 (en) * | 1969-04-03 | 1974-06-27 | Basf Ag, 6700 Ludwigshafen | Monoazo dyes, processes for their production and dye preparations |
| BE789191A (en) * | 1971-09-24 | 1973-03-22 | Cassella Farbwerke Mainkur Ag | WATER INSOLUBLE MONO-AZOIC COLORANTS |
| GB1539054A (en) * | 1976-06-24 | 1979-01-24 | Yorkshire Chemicals Ltd | Water-insoluble monoazo pyridone dyestuffs |
-
1980
- 1980-06-07 DE DE19803021555 patent/DE3021555A1/en active Granted
- 1980-06-13 IT IT48961/80A patent/IT1128162B/en active
- 1980-06-13 DD DD80221831A patent/DD151953A5/en unknown
- 1980-06-16 GB GB8019623A patent/GB2054632B/en not_active Expired
- 1980-06-16 CA CA354,040A patent/CA1128501A/en not_active Expired
- 1980-06-16 YU YU1591/80A patent/YU42510B/en unknown
- 1980-06-17 AT AT0318980A patent/AT382632B/en not_active IP Right Cessation
- 1980-06-17 ES ES492523A patent/ES8105367A1/en not_active Expired
- 1980-06-17 BR BR8003764A patent/BR8003764A/en not_active IP Right Cessation
- 1980-06-18 FR FR8013503A patent/FR2459269B1/en not_active Expired
-
1984
- 1984-04-12 HK HK317/84A patent/HK31784A/en not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| IT8048961A0 (en) | 1980-06-13 |
| FR2459269A1 (en) | 1981-01-09 |
| GB2054632A (en) | 1981-02-18 |
| ES492523A0 (en) | 1981-05-16 |
| IT1128162B (en) | 1986-05-28 |
| AT382632B (en) | 1987-03-25 |
| FR2459269B1 (en) | 1986-07-18 |
| ATA318980A (en) | 1986-08-15 |
| HK31784A (en) | 1984-04-19 |
| GB2054632B (en) | 1983-05-05 |
| DD151953A5 (en) | 1981-11-11 |
| YU159180A (en) | 1983-02-28 |
| DE3021555C2 (en) | 1988-12-08 |
| DE3021555A1 (en) | 1981-01-22 |
| YU42510B (en) | 1988-10-31 |
| ES8105367A1 (en) | 1981-05-16 |
| BR8003764A (en) | 1981-01-13 |
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