GB2028857A - Monoazo dyestuff, process for the preparation thereof and use thereof - Google Patents
Monoazo dyestuff, process for the preparation thereof and use thereof Download PDFInfo
- Publication number
- GB2028857A GB2028857A GB7928179A GB7928179A GB2028857A GB 2028857 A GB2028857 A GB 2028857A GB 7928179 A GB7928179 A GB 7928179A GB 7928179 A GB7928179 A GB 7928179A GB 2028857 A GB2028857 A GB 2028857A
- Authority
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- United Kingdom
- Prior art keywords
- modification
- temperature
- dyestuff
- formula
- dyeing
- 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.)
- Granted
Links
- 238000000034 method Methods 0.000 title claims abstract description 45
- 239000000975 dye Substances 0.000 title claims abstract description 25
- 238000002360 preparation method Methods 0.000 title claims abstract description 7
- NYGZLYXAPMMJTE-UHFFFAOYSA-M metanil yellow Chemical group [Na+].[O-]S(=O)(=O)C1=CC=CC(N=NC=2C=CC(NC=3C=CC=CC=3)=CC=2)=C1 NYGZLYXAPMMJTE-UHFFFAOYSA-M 0.000 title description 3
- 238000012986 modification Methods 0.000 claims abstract description 51
- 238000004043 dyeing Methods 0.000 claims abstract description 25
- 239000000203 mixture Substances 0.000 claims abstract description 18
- 230000004048 modification Effects 0.000 claims abstract description 14
- 238000000227 grinding Methods 0.000 claims abstract description 12
- 239000007900 aqueous suspension Substances 0.000 claims abstract description 11
- 238000010438 heat treatment Methods 0.000 claims abstract description 11
- 238000002441 X-ray diffraction Methods 0.000 claims abstract description 10
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 10
- 239000006185 dispersion Substances 0.000 claims abstract description 10
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims description 12
- 159000000000 sodium salts Chemical class 0.000 claims description 7
- 239000007859 condensation product Substances 0.000 claims description 6
- 239000000725 suspension Substances 0.000 claims description 6
- 229920002678 cellulose Polymers 0.000 claims description 5
- 239000007788 liquid Substances 0.000 claims description 5
- 239000004094 surface-active agent Substances 0.000 claims description 5
- QTWJRLJHJPIABL-UHFFFAOYSA-N 2-methylphenol;3-methylphenol;4-methylphenol Chemical compound CC1=CC=C(O)C=C1.CC1=CC=CC(O)=C1.CC1=CC=CC=C1O QTWJRLJHJPIABL-UHFFFAOYSA-N 0.000 claims description 4
- DWAQJAXMDSEUJJ-UHFFFAOYSA-M Sodium bisulfite Chemical compound [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 claims description 4
- 125000000129 anionic group Chemical group 0.000 claims description 4
- 239000003945 anionic surfactant Substances 0.000 claims description 4
- 125000002091 cationic group Chemical group 0.000 claims description 4
- 239000003093 cationic surfactant Substances 0.000 claims description 4
- 229930003836 cresol Natural products 0.000 claims description 4
- 239000002736 nonionic surfactant Substances 0.000 claims description 4
- 239000004289 sodium hydrogen sulphite Substances 0.000 claims description 4
- 235000010267 sodium hydrogen sulphite Nutrition 0.000 claims description 4
- 239000000463 material Substances 0.000 claims description 3
- 239000003960 organic solvent Substances 0.000 claims description 3
- 229920000728 polyester Polymers 0.000 claims description 3
- BDHFUVZGWQCTTF-UHFFFAOYSA-N sulfonic acid Chemical compound OS(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-N 0.000 claims description 3
- ZMESHQOXZMOOQQ-UHFFFAOYSA-N 1-(naphthalen-1-ylmethyl)naphthalene Chemical compound C1=CC=C2C(CC=3C4=CC=CC=C4C=CC=3)=CC=CC2=C1 ZMESHQOXZMOOQQ-UHFFFAOYSA-N 0.000 claims description 2
- 239000002202 Polyethylene glycol Substances 0.000 claims description 2
- 239000000835 fiber Substances 0.000 claims description 2
- 229920001223 polyethylene glycol Polymers 0.000 claims description 2
- 239000000843 powder Substances 0.000 claims description 2
- KKEYFWRCBNTPAC-UHFFFAOYSA-L terephthalate(2-) Chemical compound [O-]C(=O)C1=CC=C(C([O-])=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-L 0.000 claims description 2
- 239000002657 fibrous material Substances 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 238000004040 coloring Methods 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- KBLAMUYRMZPYLS-UHFFFAOYSA-N 2,3-bis(2-methylpropyl)naphthalene-1-sulfonic acid Chemical compound C1=CC=C2C(S(O)(=O)=O)=C(CC(C)C)C(CC(C)C)=CC2=C1 KBLAMUYRMZPYLS-UHFFFAOYSA-N 0.000 description 4
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 230000008878 coupling Effects 0.000 description 3
- 238000010168 coupling process Methods 0.000 description 3
- 238000005859 coupling reaction Methods 0.000 description 3
- -1 diazonium azo compound Chemical class 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- PSZYNBSKGUBXEH-UHFFFAOYSA-N naphthalene-1-sulfonic acid Chemical class C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1 PSZYNBSKGUBXEH-UHFFFAOYSA-N 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- LOCWBQIWHWIRGN-UHFFFAOYSA-N 2-chloro-4-nitroaniline Chemical compound NC1=CC=C([N+]([O-])=O)C=C1Cl LOCWBQIWHWIRGN-UHFFFAOYSA-N 0.000 description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 2
- 229910052783 alkali metal Inorganic materials 0.000 description 2
- 239000012736 aqueous medium Substances 0.000 description 2
- 239000011324 bead Substances 0.000 description 2
- 239000001913 cellulose Substances 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- LQZZUXJYWNFBMV-UHFFFAOYSA-N dodecan-1-ol Chemical compound CCCCCCCCCCCCO LQZZUXJYWNFBMV-UHFFFAOYSA-N 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 2
- 229920005610 lignin Polymers 0.000 description 2
- 239000011574 phosphorus Substances 0.000 description 2
- 229910052698 phosphorus Inorganic materials 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 238000005507 spraying Methods 0.000 description 2
- LSNNMFCWUKXFEE-UHFFFAOYSA-L sulfite Chemical compound [O-]S([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-L 0.000 description 2
- 125000001273 sulfonato group Chemical group [O-]S(*)(=O)=O 0.000 description 2
- 239000002699 waste material Substances 0.000 description 2
- NPCCPMHHNIOSHL-UHFFFAOYSA-N 3-(n-ethyl-3-methylanilino)propanenitrile Chemical compound N#CCCN(CC)C1=CC=CC(C)=C1 NPCCPMHHNIOSHL-UHFFFAOYSA-N 0.000 description 1
- 229910016523 CuKa Inorganic materials 0.000 description 1
- 229920000954 Polyglycolide Polymers 0.000 description 1
- JXLHNMVSKXFWAO-UHFFFAOYSA-N azane;7-fluoro-2,1,3-benzoxadiazole-4-sulfonic acid Chemical compound N.OS(=O)(=O)C1=CC=C(F)C2=NON=C12 JXLHNMVSKXFWAO-UHFFFAOYSA-N 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 150000008049 diazo compounds Chemical class 0.000 description 1
- 239000012954 diazonium Substances 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 239000012065 filter cake Substances 0.000 description 1
- 230000003311 flocculating effect Effects 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- 239000004633 polyglycolic acid Substances 0.000 description 1
- 239000004576 sand Substances 0.000 description 1
- 238000000967 suction filtration Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B29/00—Monoazo dyes prepared by diazotising and coupling
- C09B29/06—Monoazo dyes prepared by diazotising and coupling from coupling components containing amino as the only directing group
- C09B29/08—Amino benzenes
- C09B29/0805—Amino benzenes free of acid groups
- C09B29/0807—Amino benzenes free of acid groups characterised by the amino group
- C09B29/0809—Amino benzenes free of acid groups characterised by the amino group substituted amino group
- C09B29/0811—Amino benzenes free of acid groups characterised by the amino group substituted amino group further substituted alkylamino, alkenylamino, alkynylamino, cycloalkylamino aralkylamino or arylamino
- C09B29/0823—Amino benzenes free of acid groups characterised by the amino group substituted amino group further substituted alkylamino, alkenylamino, alkynylamino, cycloalkylamino aralkylamino or arylamino substituted by CN
- C09B29/0825—Amino benzenes free of acid groups characterised by the amino group substituted amino group further substituted alkylamino, alkenylamino, alkynylamino, cycloalkylamino aralkylamino or arylamino substituted by CN having N(-alkenylene-CN/-alkynylene-CN)(-aliphatic residue-CN)
-
- 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
- C09B29/06—Monoazo dyes prepared by diazotising and coupling from coupling components containing amino as the only directing group
- C09B29/08—Amino benzenes
-
- 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
- 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
Abstract
The alpha -modification of the dyestuff of the formula <IMAGE> characterised by the X-ray diffraction pattern shown in Figure 2 is unstable under certain dyeing conditions. The invention relates to another modification, the beta -modification, characterised by the X-ray diffraction pattern shown in Figure 1 which is stable under dyeing conditions and so is suitable for use in dyeing such articles as cross-wound packages. Process for the preparation of the beta - modification from the alpha -modification and dyeing compositions comprising the beta -modification may be prepared by a) heating the alpha -modification in an aqueous suspension to a temperature of 80-130 DEG C; or b) grinding the alpha - modification in the presence of one or more dispersion agents at a temperature of 80-90 DEG C. <IMAGE>
Description
SPECIFICATION
Monoazo dyestuff, process for the preparation thereof and use thereof
The present invention relates to monoazo dyestuff, process for the preparation thereof and use thereof.
The present invention provides a crystallographic modification (hereinafter termed the p- modification) of the dyestuff of the formula
which gives the X-ray diffraction pattern having reflections at the glancing angles 0 (CuK,rays) indicated below and the intensities specified:
6 6.0 8.6 9.5 12.1 12.7 13.4 14.8 relative intensity 100 22 27 57 49 38 31 The characteristic diffraction pattern is shown in Figure 1.
The dyestuff of the above formula may be obtained by diazotisation of 2-chloro-4-nitroaniline in aqueousvhydrochloric acid and the coupling of the resulting diazonium azo compound in solution to Nethyl-N-cyanoethyl-m-toluidine in a solution of dilute hydrochloric acid. Coupling yields the amodification which gives the X-ray diffraction pattern shown in Figure 2 with reflections having the intensities specified at the following glancing angles 6(CuKa rays)::
6 2.6 6.2 8.7 12.8 13.4 13.8 relative intensity 38 100 26 45 52 27 Under dyeing conditions, for example high temperatures, and in the presence of dyeing auxiliaries the p-modification undergoes substantially no further modification with regard to crystal size or form so that the colouring .properties and the stability of the dispersion remain unchanged contrary to the a- modification which is not stable under similar dyeing conditions.
The present invention also provides a process for the preparation of the ,B-modification which comprises
a) heating an aqueous suspension of the a-modification at a temperature in the range of from 80
to 1 300C for 2 hours and/or
b) grinding the a-modification in the presence of one or more dispersion agents at a temperature
in the range of from 80 to 900C.
Process (a) is preferably carried out at a temperature in the range of from 90 to 1 00C. Optionally this process may be carried out under pressure. It is also preferred to add, at any time during the process, one or more water-soluble organic solvents, for example ethanol or glycol, and/or one or more anionic, cationic or non-ionic surfactants. The addition of the solvents and/or surfactants may be before, during or after the heating of the suspension and, indeed, each solvent or surfactant may be added separately at different times. It is also possible to add the solvent and/or surfactant in portions for example at intervals throughout the process. However the anionic, cationic or non-ionic surfactants are generally added at a temperature in the range of from 80 to 1 000C.Suitable surfactants are, for example, the sodium salt of diisobutylnaphthalene sulphonic acid, the addition product of 25 moles of ethylene oxide and 1 mole of steryl alcohol, a mixture of alkyldimethylbenzylammonium chlorides, a fatty acid polyglycolic acid ester or tertiary organic phosphorus acid esters of the addition product of 2 moles of ethylene oxide and 1 mole of lauryl alcohol.
The heating of the aqueous suspension of the a-modification in process (a) is required until substantially all of the a-modification is converted into the 8-modification, generally until at least a 95% by weight conversion has been obtained. The time required for this degree of conversion is generally at least 1 hour but is preferably heated for 2 hours.
In process (b) the dispersion agents may be added at any time during the process, for example before or during a grinding operation, and may even be added in several portions, e.g. at intervals.
Where the grinding is carried out in several stages these agents may be added between one operation and another or even between each grinding operation. Usual dispersion agents are, for example, alkylated naphthalene sulphonic acids or salts thereof, polyvinylsu Iphonates, condensation products of naphthalene sulphonic acid or a phenol with formaldehyde, alkali metal salts of iignin sulphonates or sulphite cellulose waste liquors.
The ,B-modification when obtained in the presence of a liquid may be separated from the liquid phase by filtration and subsequently submitted to known finishing operations, for example grinding with the addition of dispersion agents, for example as indicated above, i.e. alkylated naphthalene sulphonic acids or salts thereof, polyvinylsulphonates, condensation products of napththalene sulphonic acid or a phenol with formaldehyde, alkali metal salts of lignin sulphonates or sulphite cellulose waste liquors, at a temperature usual for this purpose. To obtain a fine distribution, the usual devices, for example ball
mills or sand mills, may be used.
The liquid or pulverulent compositions of the ss-modification obtained may be used without any
restrictions or limitations contrary to comparable compositions of the a-modification which is unstable
under dyeing conditions flocculating in an uncontrolled manner in aqueous medium at high
temperatures, for the dyeing of fibre materials of cellulose esters or of synthetic linear polyesters, for
example polyethylene glycol terephthalate, at a temperature in the range of from 100 to 2200 C. These
compositions do not flocculate in aqueous medium or under the action of high temperatures. This
property is of importance for the dyeing of packages, for example cross-wound packages. Moreover
dyeing tests carried out with these compositions gave better results than those of comparable, usable
compositions.
Therefore the present invention further provides a dyeing composition which comprises the /3- modification in admixture or conjunction with a suitable carrier or auxiliary and the present invention
also provides a process for the dyeing of an article which comprises contacting the articie with the - modification or dyeing composition of the invention.
The following examples illustrate the invention. Parts and percentages are be weight unless otherwise stated.
EXAMPLE 1
100 parts of a dyestuff prepared by the diazotisation of 2-chloro-4-nitroaniline in aqueous
hydrochloric acid and subsequent coupling of the diazo compound obtained in solution to a solution of
N-ethyl-N-cyanoethyl-m-toluidine in dilute hydrochloric acid, were heated in an aqueous suspension for
2 hours at 90 to 950 C. During this step the a-modification was converted into the p-modification. The dyestuff was then separated by filtration and ground with 110 parts of a condensation product of cresol, formaldehyde and sodium bisulphite, and with 20 parts of the sodium salt of diisobutylnaphthalene sulphonic acid and water in a bead mill at a temperature of not more than 500C until a fine distribution was reached. Subsequently, the composition was dried in a spraying apparatus.Upon drying a desired
content of pure dyestuff was adjusted with the sodium salt of dinaphthylmethane sulphonic acid. The
resulting powder complies with colouring requirements.
EXAMPLE 2
100 parts of the starting dyestuff obtained as described in Example 1 and being moist with water
were ground with 110 parts of a condensation product of cresol, formaldehyde and sodium bisulphite
and with 20 parts of the sodium salt of diisobutylnaphthalene sulphonic acid and water in a mill at a
temperature of from 80 to 900C until a satisfactory fine distribution is reached. There was no after
treatment prior to this step. During the grinding the a-modification was converted into the p- modification. The composition was dried in a spraying apparatus as described in Example 1 and
subsequently the content of pure dyestuff was adjusted to a desired level.
EXAMPLE 3
100 parts of the starting dyestuff obtained as described in Example 1 were converted into the ,B- modification in the manner specified in Example 1, i.e. by a 2 hours' heating of an aqueous suspension
at 90 to 950C. The cake obtained upon suction filtration being moist with water was ground with 60
parts of a condensation product of cresol, formaldehyde and sodium bisulphite, with 60 parts of the
sodium salt of a lignin sulphonate and with 20 parts of the sodium salt of diisobutylnaphthalene sulphonic acid, in the manner described in Example 1, subsequently dried and adjusted to a desired
content of pure dyestuff. The resulting pulverulent composition complies with colouring requirements in prdstice.
EXAMPLE 4
100 parts of the starting dyestuff obtained as described in Example 1 were heated in an aqueous suspension containing 10% of glycol for two hours at a temperature of from 90 to 95 C, cooled and suction filtered. The filter cake, moist with water, was ground in a bead mill with the dispersion agents
specified in Example 1, at a temperature up to 500C until the desired fine distribution was reached. A
liquid dyestuff composition was obtained having flawless colouring properties and a good stability.
EXAMPLE 5
100 parts of the starting dyestuff obtained as described in Example 1 were stirred for 2 hours at 90CC in an aqueous suspension containing 0.5 volume % of the reaction product of the tertiary organic phosphorus acid ester of lauryl alcohol with 2 moles of ethylene oxide. The dyestuff filtered off was ground as indicated in Example 1. This gives a liquid dyestuff composition having flawless colouring properties.
Claims (1)
1. The i3-modification of the dyestuff of the formula
which gives the X-ray diffraction pattern having reflections at the following glancing angles 0 and relative intensities specified
f | 6.0 8.6 9.5 | 12.1 12.7 13.4 14.8 relative intensity | 10 22 27 L57 57 49 38 31
2. The p-modification as claimed in claim 1, which gives the X-ray diffraction pattern shown in
Figure 1.
3. A process for the preparation of the p-modification claimed in claim 1, which comprises
a)
heating the a-modification of the formula (I) given in claim 1 in aqueous suspension to a
temperature in the range of from 80 to 1300C: or
b)
grinding the a-modification of the formula (I) given in claim 1 in the presence of one or more
dispersion agents at a temperature in the range of from 80 to 900C.
4. A process as claimed in claim 3, wherein, in process (a), the suspension is heated to a temperature in the range of from 90 to 11 OOC.
5. A process as claimed in claim 3 or claim 4, wherein the suspension is heated for at least 1 hour.
6. A process as claimed in claim 6, wherein the suspension is heated for 2 hours.
7. A process as claimed in any one of claims 3 to 6, wherein, in process (a), one or more watersoluble organic solvents are added.
8. A process as claimed in any one of claims 3 to 7, wherein in process (a), one or more anionic, cationic or non-ionic surfactants are added.
9. A process as claimed in claim 8, wherein the surfactant(s) is/are added at a temperature in the range of from 80 to 1000C.
1 0. A process as claimed in any one of claims 3 to 9, wherein the resulting suspension is filtered.
1 A process as claimed in claim 10, wherein the residue given is subsequently ground.
1 2. A process as claimed in claim 11, wherein the temperature during grinding does not exceed 50 C.
1 3. A process as claimed in claim 11 or claim 12, wherein one or more dispersion agents are present during grinding.
14. A process as claimed in claim 3 and 11 to 13, wherein a condensation product of cresol, formaldehyde and sodium bisulphite is present during grinding.
1 5. A process as claimed in claim 3, which is carried out substantially as described in Examples 1 to 5 herein.
1 6. A process for the preparation of a modification of the formula I given in claim 1, wherein an aqueous suspension of the a-modification is heated until substantially all of the a-modification is converted into the p-modification.
17. A process as claimed in claim 16, wherein 95% by weight of the a-modification is converted.
18. The -modification as claimed in claim 1 , whenever prepared by a process as claimed in any one of claims 3 to 1 7.
1 9. The ssmodification as claimed in claim 1 obtainable by heating an aqueous suspension of the a-modification at a temperature in the range of from 80 to 1 300C.
20. The ,B-modification as claimed in claim 19, wherein the temperature is in the range of from 90 to 1 100C.
21. The ,3-modification as claimed in claim 19 or claim 20, wherein the suspension is heated for 2 hours.
22. A dyestuff modification obtainable by heating the dyestuff of the formula I given in claim 1.
23. A dyeing composition which comprises the p-modification as claimed in any one of claims 1, 2 and 1 8 to 21 in admixture or conjunction with a suitable carrier or auxiliary.
24. A dyeing composition as claimed in claim 23, which also contains the sodium salt of dinaphthylmethane sulphonic acid.
25. A dyeing composition as claimed in claim 23 or claim 24 which is in liquid or powder form.
26. A process for the dyeing of an article which comprises contacting the article with the modification as claimed in any one of claims 1,2 and 18 to 22 or with a dyeing composition as claimed in any one of claims 23 to 25.
27. A process as claimed in claim 26, wherein the article comprises a fibre material.
28. A process as claimed in claim 27, wherein the article comprises a cellulose ester or a synthetic linear polyester material.
29. A process as claimed in claim 28, wherein the article comprises polyethylene glycol terephthalate.
30. A process as claimed in any one of claims 26 to 29, wherein the article is a package.
31. A process as claimed in claim 30, wherein the package is across-wound package.
32. A process as claimed in any one of claims 26 to 31, which is carried out at a temperature in the range of from 100 to 2200C.
33. An article whenever dyed by a process as claimed in any one of claims 26 to 32.
34. A package whenever dyed by a process as claimed in any one of claims 26 to 32.
35. A cross-wound package whenever dyed by a process as claimed in any one of claims 26 to 32.
36. The ss-modification of the dyestuff of the formula
that is stable under dyeing conditions, characterized by the X-ray diffraction pattern shown in FIGURE 1 with the characteristic reflections at the following glancing angles 6 and the relative intensities specified hereinu nder:
I 6 6.0 8.6 9.5 12.1 12.7 j 13.4 14.8 relative intensity I, 100 22 27 57 49 1 38 31 37.A process for the manufacture of the p-modification of the dyestuff of the formula
that is stable under dyeing conditions and is distinguished by the X-ray diffraction pattern shown in
FIGURE 1 with the characteristic reflections at the following glancing angles 0 and the intensities specified hereinunder::
6 l 6.0 r 8.6 | 9.5 | 12.1 j 12,7 | 13.4 | 14.8 relative intensity 100 22 27 57 49 38 31 which comprises
a) heating the a-modification unstable under dyeing conditions of the dyestuff of the formula (1)
characterized by the X-ray diffraction pattern of FIGURE 2 in aqueous suspension to a
temperature of from 80 to 1300C or
b) grinding the a-modification unstable under dyeing conditions of the dyestuff of the formula (1)
characterized by the X-ray diffraction pattern shown in FIGURE 2 in the presence of dispersion
agents at a temperature of from 80 to 900C.
38. The process as claimed in claim 37a, which comprises heating with the addition of watersoluble organic solvents.
39. The process as claimed in claim 37a, which comprises heating with the addition of anionic, cationic or non-ionic surfactants.
40. Use of the B-modification stable under dyeing conditions as claimed in claim 36 for the dyeing of fiber materials of cellulose esters or synthetic linear polyesters.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2835544A DE2835544B1 (en) | 1978-08-14 | 1978-08-14 | Color-stable monoazo dye, its production and use |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| GB2028857A true GB2028857A (en) | 1980-03-12 |
| GB2028857B GB2028857B (en) | 1983-03-09 |
Family
ID=6046988
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB7928179A Expired GB2028857B (en) | 1978-08-14 | 1979-08-14 | Monoazo dyestuff process for the preparation thereof and use thereof |
Country Status (8)
| Country | Link |
|---|---|
| JP (1) | JPS5525497A (en) |
| BE (1) | BE878252A (en) |
| BR (1) | BR7905189A (en) |
| DE (1) | DE2835544B1 (en) |
| FR (1) | FR2433559A1 (en) |
| GB (1) | GB2028857B (en) |
| IT (1) | IT1122483B (en) |
| MX (1) | MX150601A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB2123845A (en) * | 1982-06-21 | 1984-02-08 | Synthetic Dyestuff Res Ass | Crystalline monoazo dye and its production |
-
1978
- 1978-08-14 DE DE2835544A patent/DE2835544B1/en not_active Ceased
-
1979
- 1979-07-13 MX MX178483A patent/MX150601A/en unknown
- 1979-08-10 IT IT25072/79A patent/IT1122483B/en active
- 1979-08-13 JP JP10231179A patent/JPS5525497A/en active Granted
- 1979-08-13 BR BR7905189A patent/BR7905189A/en unknown
- 1979-08-14 GB GB7928179A patent/GB2028857B/en not_active Expired
- 1979-08-14 FR FR7920654A patent/FR2433559A1/en active Granted
- 1979-08-14 BE BE0/196743A patent/BE878252A/en not_active IP Right Cessation
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB2123845A (en) * | 1982-06-21 | 1984-02-08 | Synthetic Dyestuff Res Ass | Crystalline monoazo dye and its production |
Also Published As
| Publication number | Publication date |
|---|---|
| FR2433559B1 (en) | 1983-09-09 |
| JPS5525497A (en) | 1980-02-23 |
| DE2835544B1 (en) | 1979-05-31 |
| BR7905189A (en) | 1980-05-06 |
| IT1122483B (en) | 1986-04-23 |
| MX150601A (en) | 1984-06-06 |
| JPS637224B2 (en) | 1988-02-16 |
| FR2433559A1 (en) | 1980-03-14 |
| GB2028857B (en) | 1983-03-09 |
| IT7925072A0 (en) | 1979-08-10 |
| BE878252A (en) | 1980-02-14 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PCNP | Patent ceased through non-payment of renewal fee |