GB2106923A - Monoazo compounds - Google Patents
Monoazo compounds Download PDFInfo
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- GB2106923A GB2106923A GB08227462A GB8227462A GB2106923A GB 2106923 A GB2106923 A GB 2106923A GB 08227462 A GB08227462 A GB 08227462A GB 8227462 A GB8227462 A GB 8227462A GB 2106923 A GB2106923 A GB 2106923A
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- 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 2
- 150000001875 compounds Chemical class 0.000 claims abstract description 30
- 239000000460 chlorine Chemical group 0.000 claims abstract description 16
- 229910052801 chlorine Inorganic materials 0.000 claims abstract description 9
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims abstract description 8
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims abstract description 8
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims abstract description 8
- 229910052794 bromium Inorganic materials 0.000 claims abstract description 8
- 239000001257 hydrogen Substances 0.000 claims abstract description 8
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 8
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 4
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims abstract description 3
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims abstract description 3
- 239000011630 iodine Chemical group 0.000 claims abstract description 3
- 229910052740 iodine Chemical group 0.000 claims abstract description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 3
- 238000012986 modification Methods 0.000 claims description 17
- 230000008878 coupling Effects 0.000 claims description 9
- 238000010168 coupling process Methods 0.000 claims description 9
- 238000005859 coupling reaction Methods 0.000 claims description 9
- 238000000034 method Methods 0.000 claims description 9
- 239000000758 substrate Substances 0.000 claims description 5
- 238000002441 X-ray diffraction Methods 0.000 claims description 3
- 230000001747 exhibiting effect Effects 0.000 claims description 3
- 150000002431 hydrogen Chemical class 0.000 claims 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- 125000001309 chloro group Chemical group Cl* 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract description 5
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 abstract 1
- 238000004043 dyeing Methods 0.000 description 15
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
- 239000000975 dye Substances 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
- 238000002360 preparation method Methods 0.000 description 5
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000002270 dispersing agent Substances 0.000 description 3
- 229920000728 polyester Polymers 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- 239000007900 aqueous suspension Substances 0.000 description 2
- 238000000889 atomisation Methods 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 239000012954 diazonium Substances 0.000 description 2
- 150000001989 diazonium salts Chemical class 0.000 description 2
- 239000000986 disperse dye Substances 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 238000000227 grinding Methods 0.000 description 2
- 229920005610 lignin Polymers 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- 230000007935 neutral effect Effects 0.000 description 2
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 210000002268 wool Anatomy 0.000 description 2
- YHRUOJUYPBUZOS-UHFFFAOYSA-N 1,3-dichloropropane Chemical compound ClCCCCl YHRUOJUYPBUZOS-UHFFFAOYSA-N 0.000 description 1
- 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 description 1
- AZUYLZMQTIKGSC-UHFFFAOYSA-N 1-[6-[4-(5-chloro-6-methyl-1H-indazol-4-yl)-5-methyl-3-(1-methylindazol-5-yl)pyrazol-1-yl]-2-azaspiro[3.3]heptan-2-yl]prop-2-en-1-one Chemical compound ClC=1C(=C2C=NNC2=CC=1C)C=1C(=NN(C=1C)C1CC2(CN(C2)C(C=C)=O)C1)C=1C=C2C=NN(C2=CC=1)C AZUYLZMQTIKGSC-UHFFFAOYSA-N 0.000 description 1
- LOCWBQIWHWIRGN-UHFFFAOYSA-N 2-chloro-4-nitroaniline Chemical compound NC1=CC=C([N+]([O-])=O)C=C1Cl LOCWBQIWHWIRGN-UHFFFAOYSA-N 0.000 description 1
- 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 1
- 229920002284 Cellulose triacetate Polymers 0.000 description 1
- 229920000742 Cotton Polymers 0.000 description 1
- 229910017488 Cu K Inorganic materials 0.000 description 1
- 229910017541 Cu-K Inorganic materials 0.000 description 1
- FZERHIULMFGESH-UHFFFAOYSA-N N-phenylacetamide Chemical compound CC(=O)NC1=CC=CC=C1 FZERHIULMFGESH-UHFFFAOYSA-N 0.000 description 1
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 1
- 239000004952 Polyamide Substances 0.000 description 1
- 239000004902 Softening Agent Substances 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
- VJMAITQRABEEKP-UHFFFAOYSA-N [6-(phenylmethoxymethyl)-1,4-dioxan-2-yl]methyl acetate Chemical compound O1C(COC(=O)C)COCC1COCC1=CC=CC=C1 VJMAITQRABEEKP-UHFFFAOYSA-N 0.000 description 1
- 229960000583 acetic acid Drugs 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 150000001447 alkali salts Chemical class 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- BFNBIHQBYMNNAN-UHFFFAOYSA-N ammonium sulfate Chemical compound N.N.OS(O)(=O)=O BFNBIHQBYMNNAN-UHFFFAOYSA-N 0.000 description 1
- 229910052921 ammonium sulfate Inorganic materials 0.000 description 1
- 239000001166 ammonium sulphate Substances 0.000 description 1
- 235000011130 ammonium sulphate Nutrition 0.000 description 1
- 125000000129 anionic group Chemical group 0.000 description 1
- 239000003945 anionic surfactant Substances 0.000 description 1
- 125000003118 aryl group Chemical group 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
- 239000007853 buffer solution Substances 0.000 description 1
- 125000002091 cationic group Chemical group 0.000 description 1
- 239000003093 cationic surfactant Substances 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000004044 disperse dyeing Methods 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 238000005108 dry cleaning Methods 0.000 description 1
- 239000004744 fabric Substances 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 239000003517 fume Substances 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 230000002209 hydrophobic effect Effects 0.000 description 1
- 239000000395 magnesium oxide Substances 0.000 description 1
- CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 1
- AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical compound [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 0.000 description 1
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 1
- 239000002736 nonionic surfactant Substances 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 239000011368 organic material Substances 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 239000004576 sand Substances 0.000 description 1
- 235000010288 sodium nitrite Nutrition 0.000 description 1
- 239000002689 soil Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-N sulfonic acid Chemical compound OS(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-N 0.000 description 1
- 239000004753 textile Substances 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000002699 waste material 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
- 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
- C09B29/082—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 halogen
-
- 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
- C09B29/0003—Monoazo dyes prepared by diazotising and coupling from diazotized anilines
-
- 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
- C09B29/0828—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 (Image)
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Coloring (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
A compound of formula <IMAGE> in which R1 is hydrogen, chlorine, bromine or iodine; R2 is hydrogen, chlorine or bromine; R3 is -CO-R5; -COOR5; -COOCH2CH2OR5; CO &lparstr& OCH2CH2 &rparstr& 2OR5 or -SO2-R6; where R5 is C1-4alkyl R6 is methyl or ethyl; R4 is (C2-3) alkyl monosubstituted by cyano, or alpha -chloroallyl.
Description
SPECIFICATION
Improvements in or relating to organic compounds
The invention relates to monoazo compounds par ticularlyforthe use as disperse dyes.
According to the invention there is provided a compound of formula I
in which R1 is hydrogen, chlorine, bromine or iodine;
R2 is hydrogen, chlorine or bromine;
R3 is-COR; -COOR5; -COOCH2CH2OR5; -COSOCH2CH2s20Rs or -SO2-R6; where R5 is C,-,alkyl R6 is methyl or ethyl; R4 is (C2 3)alkyl monosubstituted by cyano, or y-chloroally.
preferably R1 is R' where R'1 is chlorine or bromine.
Preferably R2 is hydrogen.
Preferably R3 is R'3 where R'3 is -CO-R6; -CO-OR6; -COOCH2CH2O-R6 or -SO2CH3, more preferably -COR6; where the symbol R6 is defined above.
Preferably R4 is-CH3-CHCN.
Preferred compounds of formula I are of formula II
where R', and R'3 are as defined above.
More preferred compounds of formula I are the a and p-modifications of the compound of formula III
where the a-modification has an X-ray diffraction spectra (Cu-Kut-radiation) exhibiting lines at d-values of 19.0 (weak, diffuse); 15.5 (weak); 10.0 (very weak, diffuse); 8.5 (medium); 7.9 (medium); 3.4 (strong, diffuse) and 3.28 (weak, diffuse) A; and
where the p-modification has an X-ray diffraction spectra (Cu-K,,-radiation) exhibiting lines at d-values of 16.0 (very weak); 8.4 (strong); 8.0 (weak); 6.7 (medium); 5.65 (medium); 5.10 (weak); 5.05 (weak); 4.25 (weak); 4.15 (weak); 4.02 (weak); 3.92 (weak); 3.86 (medium); 3.78 (weak); 3.65 (medium); 3.58 (medium); 3.51 (very strong); 3.39 (very weak); 3.34 (weak); 3.28 (weak); 3.22 (weak); 3.01 (very weak) and 2.74 (very weak) A.
The p-modification is preferred to the a-modification ofthe compound of formula lil The compounds of formul I may be prepared by diazotising a compound of formula IV
and the coupling it with a compound of formula V
where the symbols R, to R4 are defined above.
The amine of formula IV and the coupling compound of formula V are known or may be produced from known compounds according to known methods. Diazotisation and coupling may be carried out according to known methods.
The p-modification of the compound of formula Ill may be formed directly after coupling by heating the a-modification (so formed on coupling) in an aqueous suspension at a pH above 3 (preferably about 4) to a temperature above 65"C (preferably 75-85"C).
Alternatively, the p-modification may be formed from the a-modification by recrystallisation in an organic medium (for example acetone or a lower alcohol such as ethanol).
When conversion of the a-modification to the p-modification is in an aqueous suspension it is desirable to perform the conversion in the presence of an anionic, cationic or non-ionic surfactant preferably a dispersing agent for example polyvinylsulphonate, dinaphthylmethane disulphonate, an alkali salt of lignin sulphonicacid orcellulosesulphite waste liquor.
The compounds of formula I are useful as disperse dyes particularly in dyeing, padding or printing processes of fibres, threads of substrates derived from synthetic or semi-synthetic hydrophobic high molecular weight organic material. Preferred substrates are linear, aromatic polyesters, cellulose 2'/2 acetate, cellulose triacetate and synthetic polyamides. The substrates may be in losse fibre, yarn or fabric form.
Dyeing, printing or padding may be carried out according to known methods, for example as described in British patent 1,114,433.
The compounds of formula I can be prepared as dyeing preparations. Such preparations are known and may be prepared for example by grinding the dyestuff in the presence of dispersing agents and/or filling agents after which the preparation may be dried by vacuum or dried by atomisation and then on the addition of water dyed, printed or padded in a short or long aqueous dyebath.
The compounds of formula I have good fastness properties. In particular they have good light fastness, thermofixation-, sublimation-, pleatingfastness, wet-fastness (such as water-, sea-water-, wash- and sweat-fastnesses), fastness to solvents, (particularly to dry-cleaning solvents), fastness to softening agents, fastness to rubbing, fastness to over-dyeing, fastness to ozone, fastness to gas fumes, fastness to corrosion, reduction fastness (when dyeing with wool), reserve on wool or cotton and fastness to chlorine properties. The compound of formula I are extremely useful in variuos permanent press processes and in "Soil Release" textile finish processes.
The p-modification of the compound formula Ill also shows good stability and is particularly useful for dyeing at temperatures over 7O'C, especially for cross spool dyeing (where the dyeing liquor is passed through the spool). it is important in cross spool dyeing not to form large crystals that agglomerate on the outer surfaces of the substrates being dyed but to form a fine dispersion (circa 1 s in size) of the dyestuff in solution in dyeing conditions.
The invention will now be illustrated by the following Examples in which all percentages and parts are by weight and all temperatures are in "C.
Example 1
a) 34.5 Parts of 2 - chloro - 4- nitroaniline, 88 parts of concentrated hydrochloric acid and 250 parts of water are stirred together for 12 hours after which 40 parts of ice are added and over a period of 40 minutes 13.8 parts of sodium nitrite in 50 parts of water are added to the mixture at 0 to 2 . The mixture is stirred for a further 2 hours whilst cooling to keep the temperature between 0 and 5" and then the soformed diazonium salt solution is filtered to remove any residual solids.A solution of 55.5 parts of 1 - (N ss- cyanoethyl - N - y- chloroallyl) - amino - 3acetylamino - benzene in 100 parts of glacial acetic acid and 200 parts of 30% hydrochloric acid at 0 to 5 is added dropwise over 45 minutes whilst stirring and cooling (by the addition of ice) to the above formed diazonium salt solution.
b) At the end of the coupling the dyestuff suspension is adjusted to pH 4with approximately 400 parts of a 30% sodium hydroxide solution, whereby the temperature rises to 40-45", after which the dyestuff suspension is heated to 80-85 by introducing steam directly into the solution and this temperature is held for 45 minutes whilst stirring. The p-modification so formed is then filtered off, washed neutral with water and dried.
c) Instead of treating the suspension as in part b) above the dyestuff may be filtered after coupling, washed neutral with water, dried and then recrystallised from ethanol or acetone. In this way the p-modification is formed having a h max in dimethylformamide of 515 nm and is a red shade.
d) The coupling component 1 - (N-ss- cyanoethyl - N - y- chloroallyl) - amino - 3- acetylamino - benzene may be prepared by reacting 40.6 parts of 1 - (N - p - cyanoethyl)amino, 3,acetylamino benzene in 50 parts of water with 10 parts of magnesium oxide, 27 parts of 92% 1,3-dichloropropane (cis,trans) and stirring the mixture for 24 hours at 80"C. After stirring it is cooled and 200 parts of water are added and the reaction product is extracted with chloroform.
EXAMPLES 2 to 12
Further compounds of formula I
in which the symbols R, to R4 are given in the
Table below and where the nuances shown in the
Table are on polyester material; the dyestuffs being applied to polyester material according to known methods) may be prepared in a similar manner to
Example 1a) foliowed by pouring the mixture into 500 parts of water, filtering, washing in non-acidic water and then drying.
TABLE
Example R1 R2 R3 R4 shade h max No.
2 CI H -COC2H5 -CH,CH,CN Red 516 3 Br H -COCH3 do. do. 517 4 H H do. do. scarlet 495 5 Cl CI -COOCH2CH3OC2H5 do. red 517 6 CI H -COCH3 -CH2CH=CHCl do. 521 7 Cl H -CO(CH2)3CH3 -CH2CH2CN do. 516 3 Cl H -COOCH3 do. do. 511 9 Cl H -COO(CH2)3CH3 do. do. 513 10 Cl H -COOCH2CH2OC2H5 do. do. 511 11 Cl H -SO2CH3 do. do. 508 12 Cl H do. -CH2CH=CHCl do. L 514 Application Example
a) An ultra disperse dyeing preparation is produced by sand grinding the p-modification of the dyestuff of Example 1 [formed according to Example 1b) or lc)J in the presence of a lignin sulphonate dispersing agent followed by atomisation to give particles of average size 1 y or less and a coupage ratio of 3:10.
b) 6 Parts of the ultra disperse preparation of a) above are dispersed in 1000 parts of water and then introduced into a dyeing autoclave having a circulating liquor of 13,000 parts water and a buffer solution of 30 parts ammonium sulphate and 0.3 parts of formic acid at 60". A precleaned and pressed cross spool (1000 parts of P.E. yarn on a plastic spool) is introduced into the autoclave which is then closed and the liquor is heated over 35 minutes from 60 to 130 . After 15 minutes at 1303 the liquor is cooled to 80 , the bath emptied and the spool thoroughly washed with cold water. The spool is then spin-dried and then further dried in a drying machine. A pure, level red dyeing having a deep shade is produced, substantially free of undesired deposits with extremely good wet- and rub-fastnesses. The backwater of the dyeing is practically colourless and no traces of deposits are found in the dyeing apparatus which can immediately be used for the next dyeing.
Claims (11)
1. A compound of formula I
in which Ri is hydrogen, chlorine, bromine or iodine;
R2 is hydrogen, chlorine or bromine;
R3 is-COR5; -COORs; -COOCH2CH2OR5; -COSOCH2)2ORs or-SO3-116; where 115 is C,~4alkyl R6 is methyl or ethyl; R4 is (X2~3)alkyl monosubstituted by cyano, or y-chloroallyl.
2. A compound as claimed in Claim 1, in which R, is R' where R' is chlorine or bromine.
3. A compound as claimed in Claim 1 or Claim 2, in which 113 is hydrogen.
4. A compound as claimed in any one of Claim 1 to 3, in which R3 is R'3 where R'3 is-CO-R6,-COOR6; -COOCH2CH2O-R6 or SO2CH3 where 116 is as defined in Claim 1.
5. A compound as claimed in any one of the preceding claims in which R4 is-CH2-CH2CN.
6. A compound as claimed in Claim 1 of the formula Ill
7. The p-modification of the compound of Claim 6,
where the p-modification has an X-ray diffraction spectra (CU-Kα1-radiation) exhibiting lines at d-values of 16.0 (very weak); 8.4 (strong); 8.0 (weak); 6.7 (medium); 5.65 (medium); 5.10 (weak); 5.05 (weak); 4.25 (weak); 4.15 (weak); 4.02 (weak); 3.92 (weak); 3.86 (medium); 3.78 (weak); 3.65 (medium); 3.58 (medium); 3.51 (very strong); 3.39 (very weak); 3.34 (weak); 3.28 (weak); 3.22 (weak); 3.01 (very weak) and 2.74 (very weak) A.
8. A process for preparing a compound as claimed in Claim 1 comprising diazotising a compound of formula IV
and then coupling it with a compound of formula V
where the symbols R, to R4 are defined in Claim 1.
9. A compound according to Claim 1 substantially as herein described with reference to any one of Examples 1 to 12.
10. A process according to Claim 8 substantially as herein described with reference to any one of
Examples 1 to 12.
11. A substrate when dyed with a compound according to Claim 1 or according to a method substantially as herein described with reference to the application example.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE3139092 | 1981-10-01 | ||
| DE3146835 | 1981-11-26 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| GB2106923A true GB2106923A (en) | 1983-04-20 |
| GB2106923B GB2106923B (en) | 1984-09-26 |
Family
ID=25796483
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB08227462A Expired GB2106923B (en) | 1981-10-01 | 1982-09-27 | Monoazo compounds |
Country Status (7)
| Country | Link |
|---|---|
| BR (1) | BR8205710A (en) |
| CA (1) | CA1182449A (en) |
| CH (1) | CH653047A5 (en) |
| ES (1) | ES516113A0 (en) |
| FR (1) | FR2514017B1 (en) |
| GB (1) | GB2106923B (en) |
| IT (1) | IT1189368B (en) |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR1487636A (en) * | 1965-07-23 | 1967-07-07 | Hoechst Ag | Azo dyes and their preparation |
| NL6915769A (en) * | 1968-11-08 | 1970-05-12 | ||
| DE2249217A1 (en) * | 1972-10-07 | 1974-04-18 | Hoechst Ag | PROCESS FOR COLORING SYNTHETIC FIBER MATERIALS FROM ORGANIC SOLVENTS |
-
1982
- 1982-09-21 CH CH5579/82A patent/CH653047A5/en not_active IP Right Cessation
- 1982-09-24 FR FR8216261A patent/FR2514017B1/en not_active Expired
- 1982-09-27 GB GB08227462A patent/GB2106923B/en not_active Expired
- 1982-09-29 IT IT49185/82A patent/IT1189368B/en active
- 1982-09-29 CA CA000412454A patent/CA1182449A/en not_active Expired
- 1982-09-29 BR BR8205710A patent/BR8205710A/en unknown
- 1982-09-30 ES ES516113A patent/ES516113A0/en active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| GB2106923B (en) | 1984-09-26 |
| ES8400471A1 (en) | 1983-11-01 |
| FR2514017A1 (en) | 1983-04-08 |
| BR8205710A (en) | 1983-08-30 |
| CA1182449A (en) | 1985-02-12 |
| IT1189368B (en) | 1988-02-04 |
| IT8249185A0 (en) | 1982-09-29 |
| CH653047A5 (en) | 1985-12-13 |
| ES516113A0 (en) | 1983-11-01 |
| FR2514017B1 (en) | 1986-11-07 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PCNP | Patent ceased through non-payment of renewal fee |