GB2054632A - Improvements in or relating to organic compounds - Google Patents
Improvements in or relating to organic compounds Download PDFInfo
- Publication number
- GB2054632A GB2054632A GB8019623A GB8019623A GB2054632A GB 2054632 A GB2054632 A GB 2054632A GB 8019623 A GB8019623 A GB 8019623A GB 8019623 A GB8019623 A GB 8019623A GB 2054632 A GB2054632 A GB 2054632A
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- 150000002894 organic compounds Chemical class 0.000 title description 2
- 238000012986 modification Methods 0.000 claims abstract description 30
- 150000001875 compounds Chemical class 0.000 claims abstract description 21
- 238000000034 method Methods 0.000 claims description 16
- 238000004043 dyeing Methods 0.000 claims description 15
- 238000002360 preparation method Methods 0.000 claims description 12
- 239000000758 substrate Substances 0.000 claims description 10
- 239000002609 medium Substances 0.000 claims description 9
- 238000010438 heat treatment Methods 0.000 claims description 7
- 238000002441 X-ray diffraction Methods 0.000 claims description 4
- 230000008878 coupling Effects 0.000 claims description 4
- 238000010168 coupling process Methods 0.000 claims description 4
- 238000005859 coupling reaction Methods 0.000 claims description 4
- ALYNCZNDIQEVRV-UHFFFAOYSA-N aniline-p-carboxylic acid Natural products NC1=CC=C(C(O)=O)C=C1 ALYNCZNDIQEVRV-UHFFFAOYSA-N 0.000 claims description 3
- 239000012736 aqueous medium Substances 0.000 claims description 2
- 230000002209 hydrophobic effect Effects 0.000 claims description 2
- 230000001747 exhibiting effect Effects 0.000 claims 2
- 229910017488 Cu K Inorganic materials 0.000 claims 1
- 229910017541 Cu-K Inorganic materials 0.000 claims 1
- 239000003795 chemical substances by application Substances 0.000 claims 1
- -1 para-aminobenzoic acid benzyl ester Chemical class 0.000 claims 1
- 239000013078 crystal Substances 0.000 abstract description 6
- 230000004048 modification Effects 0.000 abstract description 6
- 239000000975 dye Substances 0.000 description 19
- 239000000725 suspension Substances 0.000 description 11
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- 239000000203 mixture Substances 0.000 description 5
- 238000001035 drying Methods 0.000 description 4
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 4
- 239000004094 surface-active agent Substances 0.000 description 4
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 125000000129 anionic group Chemical group 0.000 description 3
- 239000007900 aqueous suspension Substances 0.000 description 3
- PHHWLDOIMGFHOZ-UHFFFAOYSA-L disodium;dinaphthalen-1-ylmethanedisulfonate Chemical compound [Na+].[Na+].C1=CC=C2C(C(C=3C4=CC=CC=C4C=CC=3)(S(=O)(=O)[O-])S([O-])(=O)=O)=CC=CC2=C1 PHHWLDOIMGFHOZ-UHFFFAOYSA-L 0.000 description 3
- 239000002270 dispersing agent Substances 0.000 description 3
- 239000000835 fiber Substances 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 229920000728 polyester Polymers 0.000 description 3
- 238000005406 washing Methods 0.000 description 3
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 2
- 229940093475 2-ethoxyethanol Drugs 0.000 description 2
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- BFNBIHQBYMNNAN-UHFFFAOYSA-N ammonium sulfate Chemical compound N.N.OS(O)(=O)=O BFNBIHQBYMNNAN-UHFFFAOYSA-N 0.000 description 2
- 229910052921 ammonium sulfate Inorganic materials 0.000 description 2
- 239000001166 ammonium sulphate Substances 0.000 description 2
- 235000011130 ammonium sulphate Nutrition 0.000 description 2
- LLEMOWNGBBNAJR-UHFFFAOYSA-N biphenyl-2-ol Chemical compound OC1=CC=CC=C1C1=CC=CC=C1 LLEMOWNGBBNAJR-UHFFFAOYSA-N 0.000 description 2
- 150000001989 diazonium salts Chemical class 0.000 description 2
- 235000019253 formic acid Nutrition 0.000 description 2
- 239000002245 particle Substances 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- 229920002284 Cellulose triacetate Polymers 0.000 description 1
- IOVCWXUNBOPUCH-UHFFFAOYSA-M Nitrite anion Chemical compound [O-]N=O IOVCWXUNBOPUCH-UHFFFAOYSA-M 0.000 description 1
- 239000004952 Polyamide Substances 0.000 description 1
- 238000004279 X-ray Guinier Methods 0.000 description 1
- NNLVGZFZQQXQNW-ADJNRHBOSA-N [(2r,3r,4s,5r,6s)-4,5-diacetyloxy-3-[(2s,3r,4s,5r,6r)-3,4,5-triacetyloxy-6-(acetyloxymethyl)oxan-2-yl]oxy-6-[(2r,3r,4s,5r,6s)-4,5,6-triacetyloxy-2-(acetyloxymethyl)oxan-3-yl]oxyoxan-2-yl]methyl acetate Chemical compound O([C@@H]1O[C@@H]([C@H]([C@H](OC(C)=O)[C@H]1OC(C)=O)O[C@H]1[C@@H]([C@@H](OC(C)=O)[C@H](OC(C)=O)[C@@H](COC(C)=O)O1)OC(C)=O)COC(=O)C)[C@@H]1[C@@H](COC(C)=O)O[C@@H](OC(C)=O)[C@H](OC(C)=O)[C@H]1OC(C)=O NNLVGZFZQQXQNW-ADJNRHBOSA-N 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 1
- 239000004744 fabric Substances 0.000 description 1
- 238000000227 grinding Methods 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- LVWZTYCIRDMTEY-UHFFFAOYSA-N metamizole Chemical compound O=C1C(N(CS(O)(=O)=O)C)=C(C)N(C)N1C1=CC=CC=C1 LVWZTYCIRDMTEY-UHFFFAOYSA-N 0.000 description 1
- 235000010292 orthophenyl phenol Nutrition 0.000 description 1
- 239000004306 orthophenyl phenol Substances 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Substances [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- PYBOTXJDCXMILP-ICYLSCGJSA-M sodium;(z,12r)-12-hydroxy-2-sulfooctadec-9-enoate Chemical compound [Na+].CCCCCC[C@@H](O)C\C=C/CCCCCCC(C([O-])=O)S(O)(=O)=O PYBOTXJDCXMILP-ICYLSCGJSA-M 0.000 description 1
- GGHPAKFFUZUEKL-UHFFFAOYSA-M sodium;hexadecyl sulfate Chemical compound [Na+].CCCCCCCCCCCCCCCCOS([O-])(=O)=O GGHPAKFFUZUEKL-UHFFFAOYSA-M 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 238000009987 spinning Methods 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 239000002351 wastewater Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B67/00—Influencing the physical, e.g. the dyeing or printing properties of dyestuffs without chemical reactions, e.g. by treating with solvents grinding or grinding assistants, coating of pigments or dyes; Process features in the making of dyestuff preparations; Dyestuff preparations of a special physical nature, e.g. tablets, films
- C09B67/0001—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
The present invention relates to a compound of formula I <IMAGE> and the use of the gamma and delta crystal modifications thereof as dyestuffs.
Description
SPECIFICATION
Improvements in or relating to organic compounds
The present invention relates to pyridone disperse dyestuffs.
More particularly, the present invention provides a compound of formula I
The compound of formula I exists in 4 different crystal modifications.
When diazotized para-amino benzoic acid benzyl ester is coupled with 1-n-butyl-3-cyano-4- methyl-6-hydroxy-pyridone-2 in accordance with known methods, preferably in aqueous medium having a pH of from 3-6 at 0-1 0 C, the a-modification is obtained. The ssmodification may be obtained by recrystallizing the dried a modification from 2-ethoxyethanol.
The y-modification may be obtained by heating an aqueous suspension of the a-modification which has been adjusted to a pH between 2 and 4 for 1 to 5 hours at temperatures between 80 and 1 00 C. Preferably a cold suspension of the dye is adjusted to pH 3 and is heated at temperatures of from 90 to 95"C for approximately 2 hours. In addition the suspension suitably contains an anionic surface active agent. The suspension may be formed with the dried and isolated a-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 y-modification can also be obtained by repeated recrystallization of pure dry amodification from 2-methoxy- or 2-ethoxyethanol.
The 6modification may be obtained by heating an aqueous suspension of any of the other crystal forms at approximately 1 30 C in an autoclave. Heating may be effected for from one to 4 hours. Here again the suspension suitably contains an anionic surface active agent. Once the Bform has been obtained it is advantageous to seed the suspension before the heat treatment for further production.
The four modifications of the compound of formula I may be distinguished by their X-ray diffraction spectra. Table 1 shows the interplanar spacing (d-values) in Angström units of the observed lines in the X-ray diffraction spectrum as measured by a Guinier/De Wolff camera using Cu-Ka- radiation. The intensity (I) of the lines was estimated on a 4 step scale: strong (s), medium (m), weak (w) very weak (vw). A diffuse line is indicated by the letter d.
TABLE 1 a-modification ss-modification d-value d-value
Line No. ( ) I Line No. (A) 1 16,8 vw 1 8,6 wd 2 14,0 w 2 8,0 vwd 3 11,5 vw 3 7,4 wd 4 10,0 m 4 5,6 wd 5 8,0 vw 5 4,5 w 6 7,55 vw 6 4,3 vwd 7 7,0 w 7 3,9 vwd 8 6,8 w 8 3,6 vwd 9 5,99 vw 9 3,38 vwd 10 5,8 vw 10 3,15 vwd 11 5,7 vw 11 2,6 vwd 12 5,4 vw 13 5,35 vw 14 4,75 vw 15 4,35 vw d 16 4,2 vw 17 4,0 vw 18 3,95 vw 19 3,85 vw 20 3,48 s 21 3,38 m 22 3,29 m 23 3,19 vw 24 3,09 vw 25 2,25 vw
Table 1 continued y-modification 8-modification d-value d-value
Line No. (A) I Line No. ( ) 1 16,5 vw 1 14,1 m
2 11,5 w 2 11,5 vw
3 10,6 w 3 10,3 vw
4 8,4 vw 4 8,2 m
5 8,0 w 5 7,8 m
6 7,5 w 6 7,2 w
7 5,65 vw 7 5,08 w
8 5,48 m 8 4,9 vw
9 5,43 m 9 4,5 vw 10 4,99 vw 10 4,25 vw 11 4,8 w 11 3,69 m 12 4,62 w 12 3,48 w 13 4,45 w 13 3,4 m 14 4,21 vw 14 3,19 w 15 4,13 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 20 3,4 s 21 3,18 m 22 2,94 w 23 2,9 w 24 2,78 vw 25 2,73 vw 26 2,48 vw 27 2,23 vw 28 2,18 vw 29 1,873 wd
The compound of formula I is useful for dyeing and printing synthetic or semi-synthetic high molecular weight, hydrophobic organic substrates from aqueous suspension. The preferred substrates are those consisting of or comprising linear, aromatic polyesters, cellulose 2+ acetate, cellulose triacetate and synthetic polyamides.The substrate may be in loose fibre, yarn or 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 a- and ss-modifications are unsuitable for dyeing at high temperatures, e.g. temperatures of over 1 00,C, under pressure as they have a tendency to form large crystals under these conditions, therefore when the dyestuff is to be employed for high-temperature dyeings the a- and ss-modifications should be converted to the y- and/or 6modifications or alternatively they should be admixed with at least 10 times their weight of the stable y- and 6modifications.The dyestuff of the invention, especially the yand 6modifications, has good resistance to hydrolysis and good build-up power on the abovementioned substrates and gives dyeings having notable fastness, 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.
Example 1
18.25 Parts paminobenzoic 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 then cooled to 0-5" with ice. The excess nitrite is destroyed with amidosulphonic acid and the solution is filtered clear.
A solution of 1 6.2 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 diazonium compound remains, the mixture is stirred overnight whereupon the suspension reaches room temperature and the excess diazonium compound disappears. After filtering, washing and drying at 60 in vacuo good yields or pure dyestuff are obtained. The dyestuff obtained is in the a-crystal modification form.
Example 2
Preparation of the y-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 of a surface active agent (e.g.
sodium dinaphthylmethane disulphonate) is added, the pH is adjusted to 3 with hydrochloric acid and the mixture is heated to 85-95" for 2 hours. After filtering, washing and drying the ymodification of the dyestuff is obtained,
The unfiltered coupling suspension of the dyestuff may also be subjected to the above heat treatment in order to obtain the stable y-modification.
The stable y-modification may also be obtained by repeated recrystallization of the dried dyestuff from methyl- or ethylglycol.
Example 3
Preparation of the y-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 autoclave to a temperature of 1 30 to 132" for 2 hours. After cooling, filtering, washing and drying the Bmodification is obtained.
The unfiltered coupling suspension of the dye of Example 1 may also be used and subjected to the heat treatment described above.
Dyeing Example A
The stable modification of Example 2 or 3 is ground in the presence of a dispersing agent, e.g. ligninsulphonate and spray dried to obtain a dye preparation having a particle size of less than or equal to 1 ju, the blend containing 3 parts dye and 7 parts dispersing agent.
10 Parts of the finely dispersed dyestuff preparation is added to 1000 parts water and the whole is added at 60 to a circulating bath containing 1 3000 parts of which 30 parts are ammonium sulphate, 0,3 parts formic acid and the rest is water. Prewashed cross-wound spool (1000 parts polyester yarn) is put in the bath. The autoclave is closed and heated from 60 to 130 over 35 minutes. After 1 5 minutes at 130 the autoclave is cooled to 80 , the dyebath is 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. twice standard depth), level dyeing of a greenish yellow shade free from undissolved particles on the surface having good wet and rubbing fastnesses is obtained. The dyeing apparatus is also free from deposits of dyestuff 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 described in Example 1 are ground with 4 parts sodium dinaphthylmethandisulphonate, 4 parts sodium cetyl sulphate and 5 parts anhydrous sodium sulphate in a ball mill for 48 hours.
1 Part of the dyestuff preparation is made into a paste with water and the suspension is added through a sieve to a dyebath containing 1:2 parts sodium sulphoricinoleate (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 is heated to 98"C over 30 minutes (12 parts orthophenylphenol carrier are added at 60 ) and the substrate is dyed for 2 hours at this temperatue,
The greenish-yellow dyed fibre is washed, soaped, washed again and dried. An even dyeing with good fastnesses is obtained.
Claims (14)
1. The compound of formula I,
2. The y-modification of the compound of formula I, according to Claim 1, having the X-ray diffraction spectra (Cu-K,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) Angström.
3. The 8-modification of the compound of formula I, according to Claim 1, having the X-ray diffraction spectra (Cu-Kat-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) Angström .
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 a compound of formula I, as defined in Claim 1, substantially as hereinbefore described with reference to Example 1.
6. A compound of formula I, whenever prepared by a process according to Claim 4 or Claim 5.
7. A process for the preparation of the y-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 1 00'C.
8. A process for the preparation of the y-modification of the compound of formula I as defined in Claim 2, substantially as hereinbefore described with reference to Example 2.
9. The y-modification of the compound of formula I as defined in Claim 2, whenever obtained by a process according to Claim 7 or Claim 8.
10. A process for the preparation of the 8-modification of the compound of formula I, as defined in Claim 3, comprising heating the a-, ss or y-modification of the compound of formula I in an aqueous medium to a temperature of at least 130"C under pressure.
11. A process for the preparation of the 8-modification of the compound of formula I, as defined in Claim 3, substantially as hereinbefore described with reference to Example 3.
1 2. The 8-modification of the compound of formula I, as defined in Claim 3, whenever obtained by a process according to Claim 10 or 11.
1 3. A process for dyeing or printing substrates consisting of or comprising synthetic or semisynthetic high molecular weight, hydrophobic organic substrates comprising employing a compound according to any one of Claims 1, 2, 3, 9 and 12, as dyeing or printing agent.
14. A process according to Claim 13, in which a compound according to any one of Claims 2, 3, 9 and 1 2 is employed.
1 5. Dyed or printed substrates whenever obtained by a process according to Claim 1 3.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| 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 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| GB2054632A true GB2054632A (en) | 1981-02-18 |
| GB2054632B GB2054632B (en) | 1983-05-05 |
Family
ID=25698182
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB8019623A Expired GB2054632B (en) | 1979-06-18 | 1980-06-16 | Organic compounds |
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) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0068186A1 (en) * | 1981-06-26 | 1983-01-05 | CASSELLA Aktiengesellschaft | Colour-stable modification of a dispersion dye, its preparation process and its use |
| EP0091882A1 (en) * | 1982-04-07 | 1983-10-19 | Ciba-Geigy Ag | Stable dyestuff, process for preparing it and its use in dyeing and printing synthetic and semi-synthetic fibres |
| US5069682A (en) * | 1990-01-10 | 1991-12-03 | Cassella Aktiengesellschaft | Color-stable beta-modification of a monoazo dye, a process for its preparation, and its 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 DD DD80221831A patent/DD151953A5/en unknown
- 1980-06-13 IT IT48961/80A patent/IT1128162B/en active
- 1980-06-16 YU YU1591/80A patent/YU42510B/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
- 1980-06-17 ES ES492523A patent/ES8105367A1/en not_active Expired
- 1980-06-17 BR BR8003764A patent/BR8003764A/en not_active IP Right Cessation
- 1980-06-17 AT AT0318980A patent/AT382632B/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
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0068186A1 (en) * | 1981-06-26 | 1983-01-05 | CASSELLA Aktiengesellschaft | Colour-stable modification of a dispersion dye, its preparation process and its use |
| EP0091882A1 (en) * | 1982-04-07 | 1983-10-19 | Ciba-Geigy Ag | Stable dyestuff, process for preparing it and its use in dyeing and printing synthetic and semi-synthetic fibres |
| US5069682A (en) * | 1990-01-10 | 1991-12-03 | Cassella Aktiengesellschaft | Color-stable beta-modification of a monoazo dye, a process for its preparation, and its 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 |
Also Published As
| Publication number | Publication date |
|---|---|
| BR8003764A (en) | 1981-01-13 |
| CA1128501A (en) | 1982-07-27 |
| HK31784A (en) | 1984-04-19 |
| ES492523A0 (en) | 1981-05-16 |
| IT1128162B (en) | 1986-05-28 |
| FR2459269A1 (en) | 1981-01-09 |
| ATA318980A (en) | 1986-08-15 |
| YU42510B (en) | 1988-10-31 |
| YU159180A (en) | 1983-02-28 |
| ES8105367A1 (en) | 1981-05-16 |
| DE3021555C2 (en) | 1988-12-08 |
| DE3021555A1 (en) | 1981-01-22 |
| GB2054632B (en) | 1983-05-05 |
| IT8048961A0 (en) | 1980-06-13 |
| FR2459269B1 (en) | 1986-07-18 |
| AT382632B (en) | 1987-03-25 |
| DD151953A5 (en) | 1981-11-11 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 732E | Amendments to the register in respect of changes of name or changes affecting rights (sect. 32/1977) | ||
| PCNP | Patent ceased through non-payment of renewal fee |
Effective date: 19990616 |