GB2041391A - Improvements in or relating to monoazo dyes - Google Patents
Improvements in or relating to monoazo dyes Download PDFInfo
- Publication number
- GB2041391A GB2041391A GB8002572A GB8002572A GB2041391A GB 2041391 A GB2041391 A GB 2041391A GB 8002572 A GB8002572 A GB 8002572A GB 8002572 A GB8002572 A GB 8002572A GB 2041391 A GB2041391 A GB 2041391A
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- United Kingdom
- Prior art keywords
- alkoxy
- alkyl
- chlorine
- bromine
- compound according
- 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
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- 239000000975 dye Substances 0.000 title claims description 9
- 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 1
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 37
- -1 cyano, hydroxy Chemical group 0.000 claims abstract description 36
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims abstract description 30
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 30
- 239000000460 chlorine Substances 0.000 claims abstract description 26
- 150000001875 compounds Chemical class 0.000 claims abstract description 26
- 229910052801 chlorine Inorganic materials 0.000 claims abstract description 25
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims abstract description 23
- 229910052794 bromium Inorganic materials 0.000 claims abstract description 23
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 18
- 125000001309 chloro group Chemical group Cl* 0.000 claims abstract description 17
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims abstract description 8
- 125000001424 substituent group Chemical group 0.000 claims abstract description 7
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims abstract description 3
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims abstract description 3
- 125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 claims abstract description 3
- 125000001302 tertiary amino group Chemical group 0.000 claims abstract description 3
- 125000000217 alkyl group Chemical group 0.000 claims description 22
- 229910052739 hydrogen Inorganic materials 0.000 claims description 20
- 239000001257 hydrogen Substances 0.000 claims description 20
- 238000000034 method Methods 0.000 claims description 14
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 13
- 125000003342 alkenyl group Chemical group 0.000 claims description 9
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 claims description 9
- 125000005708 carbonyloxy group Chemical group [*:2]OC([*:1])=O 0.000 claims description 9
- 229920000728 polyester Polymers 0.000 claims description 9
- 125000000304 alkynyl group Chemical group 0.000 claims description 8
- 238000004043 dyeing Methods 0.000 claims description 7
- 125000001731 2-cyanoethyl group Chemical group [H]C([H])(*)C([H])([H])C#N 0.000 claims description 6
- 150000001412 amines Chemical class 0.000 claims description 5
- 239000000758 substrate Substances 0.000 claims description 5
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 4
- 125000005195 alkyl amino carbonyloxy group Chemical group 0.000 claims description 4
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 4
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 4
- 238000005859 coupling reaction Methods 0.000 claims description 4
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 3
- 230000008878 coupling Effects 0.000 claims description 3
- 238000010168 coupling process Methods 0.000 claims description 3
- 230000002209 hydrophobic effect Effects 0.000 claims description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 3
- 125000005394 methallyl group Chemical group 0.000 claims description 3
- 239000011368 organic material Substances 0.000 claims description 3
- 239000004753 textile Substances 0.000 claims description 3
- 229920002284 Cellulose triacetate Polymers 0.000 claims description 2
- 239000004952 Polyamide Substances 0.000 claims description 2
- 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 claims description 2
- 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 claims description 2
- 125000004442 acylamino group Chemical group 0.000 claims description 2
- 125000003302 alkenyloxy group Chemical group 0.000 claims description 2
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 2
- 125000005133 alkynyloxy group Chemical group 0.000 claims description 2
- 125000005336 allyloxy group Chemical group 0.000 claims description 2
- 125000003118 aryl group Chemical group 0.000 claims description 2
- 125000000043 benzamido group Chemical group [H]N([*])C(=O)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 2
- 125000006515 benzyloxy alkyl group Chemical group 0.000 claims description 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 2
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 2
- 125000005359 phenoxyalkyl group Chemical group 0.000 claims description 2
- 125000003884 phenylalkyl group Chemical group 0.000 claims description 2
- 229920002647 polyamide Polymers 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims 2
- 241000237519 Bivalvia Species 0.000 claims 1
- 125000004466 alkoxycarbonylamino group Chemical group 0.000 claims 1
- 125000004457 alkyl amino carbonyl group Chemical group 0.000 claims 1
- 229920002678 cellulose Polymers 0.000 claims 1
- 239000001913 cellulose Substances 0.000 claims 1
- 235000020639 clam Nutrition 0.000 claims 1
- 125000001140 1,4-phenylene group Chemical group [H]C1=C([H])C([*:2])=C([H])C([H])=C1[*:1] 0.000 abstract description 2
- 125000001786 isothiazolyl group Chemical group 0.000 abstract description 2
- 239000000986 disperse dye Substances 0.000 abstract 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 6
- 239000000203 mixture Substances 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- 150000002431 hydrogen Chemical group 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 4
- 150000003254 radicals Chemical class 0.000 description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 3
- 229960000583 acetic acid Drugs 0.000 description 3
- 239000012362 glacial acetic acid Substances 0.000 description 3
- 235000019260 propionic acid Nutrition 0.000 description 3
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 3
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- 239000000835 fiber Substances 0.000 description 2
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
- 125000006563 (C1-3) alkylaminocarbonyl group Chemical group 0.000 description 1
- PJQFZPWSFDVYIF-UHFFFAOYSA-N 5-amino-3-methyl-1,2-thiazole-4-carbonitrile Chemical compound CC1=NSC(N)=C1C#N PJQFZPWSFDVYIF-UHFFFAOYSA-N 0.000 description 1
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N N-phenyl amine Natural products NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 1
- DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical compound [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 description 1
- 239000004141 Sodium laurylsulphate Substances 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- SYKNUAWMBRIEKB-UHFFFAOYSA-N [Cl].[Br] Chemical group [Cl].[Br] SYKNUAWMBRIEKB-UHFFFAOYSA-N 0.000 description 1
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 description 1
- 150000001241 acetals Chemical class 0.000 description 1
- 150000001555 benzenes Chemical class 0.000 description 1
- 125000001231 benzoyloxy group Chemical group C(C1=CC=CC=C1)(=O)O* 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000006193 diazotization reaction Methods 0.000 description 1
- 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 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 238000000227 grinding Methods 0.000 description 1
- 238000009998 heat setting Methods 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- VQTGUFBGYOIUFS-UHFFFAOYSA-N nitrosylsulfuric acid Chemical compound OS(=O)(=O)ON=O VQTGUFBGYOIUFS-UHFFFAOYSA-N 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 235000019333 sodium laurylsulphate Nutrition 0.000 description 1
- 235000010288 sodium nitrite Nutrition 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- GGHPAKFFUZUEKL-UHFFFAOYSA-M sodium;hexadecyl sulfate Chemical compound [Na+].CCCCCCCCCCCCCCCCOS([O-])(=O)=O GGHPAKFFUZUEKL-UHFFFAOYSA-M 0.000 description 1
- 238000001694 spray drying Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000000859 sublimation Methods 0.000 description 1
- 230000008022 sublimation Effects 0.000 description 1
- 239000001117 sulphuric acid Substances 0.000 description 1
- 235000011149 sulphuric acid Nutrition 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 229920002994 synthetic fiber Polymers 0.000 description 1
- 239000004758 synthetic textile Substances 0.000 description 1
- 238000001291 vacuum drying 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
- C09B29/0025—Monoazo dyes prepared by diazotising and coupling from diazotized amino heterocyclic compounds
- C09B29/0074—Monoazo dyes prepared by diazotising and coupling from diazotized amino heterocyclic compounds the heterocyclic ring containing nitrogen and sulfur as heteroatoms
- C09B29/0077—Monoazo dyes prepared by diazotising and coupling from diazotized amino heterocyclic compounds the heterocyclic ring containing nitrogen and sulfur as heteroatoms containing a five-membered heterocyclic ring with one nitrogen and one sulfur as heteroatoms
- C09B29/0081—Isothiazoles or condensed isothiazoles
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Coloring (AREA)
- Plural Heterocyclic Compounds (AREA)
- Thiazole And Isothizaole Compounds (AREA)
Abstract
The present invention relates to isothiazolyl-containing azo compounds of formula I, <IMAGE> in which R1 is (C1-4)alkyl optionally mono- substituted by chlorine, bromine, cyano, hydroxy, (C1-2)alkoxy, (C1-2)alkoxy-carbonyl or phenyl; or phenyl optionally substituted by up to two substituents selected from chlorine, bromine, methyl and (C1-2)alkoxy, K is a radical of the 1,4-phenylene series, and A is a secondary or tertiary amino group which contains an unsaturated aliphatic radical, which compounds are useful as disperse dyes.
Description
SPECIFICATION
Improvements in or relating to organic compounds
The present invention relates to isothiazolyl-containing azo compounds, their preparation and use as disperse dyestuffs.
More particularly, the present invention provides compounds of formula I,
in which R1 is (C1-4)alkyl optionally mono-substituted by chlorine, bromine, cyano, hydroxy,
(C1-2)alkoxy, (C1-2)alkoxycarbonyl or phenyl; or phenyl optionally substituted by up to two
substituents selected from the group consisting of chlorine, bromine, methyl and
(C1-2)alkoxy,
K is a radical of the 1 ,4-phenylene series, and
A is a secondary or tertiary amino group which contains an unsaturated aliphatic radical.
Suitable unsaturated aliphatic radicals are radicals of the alkenyl or alkynyl series.
The radical - K - A is preferably of formula
in which R2 is hydrogen, chlorine, bromine, (C1~2) alkyl or (C1-2)alkoxy,
R3 si hydrogen, methyl or acylamino,
R4 is (C3-4)alkynyl; or (C3-4)alkenyl optionally monosubstituted by chlorine, bromine, or phenyl,
R5 is hydrogen; (C3-4)alkynyl; (C3-4)alkenyl optionally monosubstituted by chlorine bromine, or
phenyl;(C1-3)alkyl optionally monomsubstituted by chlorine, bromine, hydroxyl, cyano,
thiocyano, (C1-3)alkoxy, (C3-4)alkenyloxy, (C3-4)alkynyloxy, formyloxy, alkyl(C1-3)carbonyloxy,
alkoxy(C1-3)carbonyl, alkoxy(C1-3)carbonyloxy, chloro- or bromo-alkyl(C1-2)carbonyloxy, benzoy
loxy, phenyl, phenoxy, phenyl(C1-2), alkoxy, aminocarbonyl, aminocarbonyloxy, (C1-3)-alkyl- or
di(C1-3)alkyl-amino-carbonyl or - carbonyloxy or phenylaminocarbonyl or - carbonyloxy; (C5-7)
cycloalkyl optionally substituted by up to three methyl groups; or phenyl optionally
substituted by up to two substituents selected from the group consisting of chlorine, bromine,
methyl and (C1-2) alkoxy,
It will be appreciated that the molecule is free from acetal e.g. -N-C-O- and O-C-O moieties.
By acyamino as a significance for R3 is meant radical of the carbonylamino and sulphonylamino
series.
Any alkyl radical as R1 preferably contains 1 to 3, more preferably 1 to 2, carbon atoms and is
preferably unsubstituted.
Any alkyl as R2 is preferably methyl.
R1 is preferably R;, where R1' is (C1-3)alkyl; or phenyl optionally substituted by up to two
substituents selected from chlorine, bromine, methyl and (C1-2)alkoxy. More preferably R't is methyl.
R2 is preferably R2 where R2 is hydrogen, methyl, chlorine or (C1-2)alkoxy, more preferably
hydrogen or (C1-2)alkoxy, with hydrogen being especially preferred.
R3 is preferably R3, where F3, is hydrogen; methyl; alkyl(C1-2)carbonylamino; benzoylamino; (C1-2)-
alkoxycarbonylamino; benzyloxycarbonylamino; hydroxy-, chloro-, bromo-, (C1-2)alkoxy-, phenyl-,
phenoxy- or benzyloxy-alkyl(C1-2)carbonylamino; 2-(C1-2)alkoxyethoxycarbonylamino; or
methylsulphonylamino. Most preferably R3' is alkyl(C1-2)carbonylamino.
R4 is preferably R4', where R4' is (C3-4)alkynyl; or (C3-4)alkenyl optionally monosubstituted by
chlorine or bromine. More preferably R4 is F'4, where R'4 is allyl, 3-chloroallyl or 2-methylallyl, with 3
chloroallyl being especially preferred.
R5 is preferably R5', where R5' is hydrogen, (C3-4) alkynyl; (C3-4)alkenyl optionally monosubstituted
by chlorine or bromine; (C1-3)alkyl optionally monosubstituted by chlorine, bromine, hydroxyl, cyano,
thiocyano, allyloxy, benzyloxy, propynyloxy, alkyl(C1-2)carbonyloxy, alkoxy(C12)carbonyl, alkoxy(C1~2)- carbonyloxy, (C1-2)alkoxy, phenyl, aminocarbonyl, (C1-2)alkylaminocarbonyloxy or phenylamino
carbonyloxy. More preferably R5 is Razz where R'5 is allyl, 3-chloroallyl, 2-methylallyl, cyanoethyl,
alkyl(C1-2)carbonyloxyethyl alkoxy(C1~2)carbonylethyl or benzyl, with cyanoethyl, acetoxyethyl and alkoxy(C1-2)carbonylethyl being most preferred.
Preferred dyestuffs are those of formula 1a
especially those where R3 is R3'.
More preferred are those of formula la, where R2 is R2', R3 is R3', R4 si R4' and R5 is R5', especially those where R2 is hydrogen or (Ct~2)alkoxy, R3 is alkyl(C12)carbonylamino, R4 is R'4 and R5 is Razz Even more preferred compounds of formula 1a are those where R; is methyl, R2 is hydrogen or (C12)alkoxy, preferably hydrogen, R3 is alkyl(C1-2)carbonylamino, R4 is 3-chloroallyl and R5 is cyanoethyl, acetoxyethyl or alkoxy(Ct~2)carbonylethyl.
The present invention further provides a process for the preparation of compounds of formula I, as defined above, comprising coupling a diazotised amine of formula 11,
with an amine of formula Ill, H- K -A Ill The coupling reaction may be carried out in accordance with known methods. Similarly diazotization of the amine of formula II may be effected by conventional techniques. The compounds of formulae II and Ill are either known or may be prepared in accordance with known methods from available starting materials.
The compounds of formula I are useful as disperse dyestuffs for dyeing or printing textile substrates consisting of or comprising synthetic or semi-synthetic, hydrophobic, high molecular weight.
organic materials, especially those consisting of or comprising linear, aromatic polyesters, cellulose-2 2 acetate, cellulose triacetate and synthetic polyamides.
The processing of the compounds of formula I to form dyestuff preparations may be effected in accordance with known methods for example, grinding in the presence of dispersing agents andXor fillers optionally with vacuum or spray drying.
Dyeing and printing may be effected in accordance with known methods for example, in analogy with the procedure described in French Patent 1,445,371.
The dyestuffs give brilliant dyeings and prints having good fastness notably light fastness, thermofixation fastness, sublimation fastness and pleating fastness. Furthermore, the dyestuffs are stable to hydrolysis.
The following Examples further serve to illustrate the invention. In the Examples all parts are by weight and all temperatures are in degrees Centigrade.
EXAMPLE 1
13.9 parts 5-amino-4-cyano-3-methyl-isothiazole are added slowly at O to 50 to a mixture of 107 parts nitrosylsulphuric acid (prepared by dissolving 7 parts sodium nitrite in 100 parts conc. sulphuric acid), 85 parts glacial acetic acid and 15 parts propionic acid.The mixture is then added at 0 t0 5 to a mixture of 85 parts glacial acetic acid and 15 parts propionic acid and subsequently stirred for 3 hours at O to 5 . A solution of 27.8 parts 1-acetylamino-3-(N-2'-cyanoethyl)-(N-3'-chloro-allyl)- aminobenzene in 85 parts glacial acetic acid and 1 5 parts propionic acid is added dropwise and the
resulting coupling mixture is stirred for 3 hours at O to 5 . The reaction mixture is then poured onto a
mixture of 600 parts ice and 300 parts water, whereupon the dyestuff precipitates. The dyestuff is filtered, washed salt- and acid-free with water and dried. The dyestuff obtained of formula
dyes synthetic fabrics in red shades with good fastness In the following Table further dyestuffs, which may be prepared in analogy with the procedure of Example 1, are given. TABLE
Ex. Shade on polyester No. R1 R2 R3 R4 R5 fibres 1 -CH3 H -NHCOCH3 -CH2CH=CHCl -C2H4CN red 2 -C2H5 H do. do. do. do.
3 -CH3 H -NHCOC2H5 do. do. do.
4 -C6H5 H -NHCOCH3 do. do. do.
5 do. H do. -CH2CH=CH2 do. do.
6 do. H do. -CH2C(CH3)=CH2 do. do.
7 -CH3 H do. -CH2CH=CH2 do. do.
8 do. H do. -CH2C(CH3)=CH2 do. do.
9 do. H do. -CH2CH=CHCl -CH2CH=CHCl do.
10 do. H do. -CH2CH=CH2 -CH2CH=CH2 do.
11 do. H do. -CH2CH=CH -CH2CH=CN do.
12 do. H do. -CH2CH=CHCl -C2H4OCONHC6H5 do.
13 do. H do. do. -C2H4OCOCH3 do.
14 do. H do. do. -C2H4OCOOCH3 do.
15 do. H do. do. -C2H4OCOOC2H5 do.
16 do. H do. do. -C2H4COOC2H5 do.
TABLE (cont.)
Ex. Shade on polyester No. R1 R2 R3 R4 R5 fibres 17 -CH3 H -NHCOCH3 -CH2CH=CHCl -C2H4COOCH2 red 18 do. H do. do. -CH2C6H5 do.
19 do. H -NHCOOCH3 do. -C2H4CN do.
20 do H -NHCOOC2H5 do. do. do.
21 do. H -NHCOC6H5 do. do. do.
22 do. H -CH3 do. do. do 23 do. H do. do. do. scarlet 24 do. H do. -CH2CH=CH2 -CH2CH=CH2 red 25 do. H H do. do. do.
26 do. H H -CH2CH=CHCl -CH2CH=CHCl do.
27 do. H H do. -C2H5 do.
28 do. H -CH3 do. do.
29 do. H -NHCOCH3 do. do. violet 30 do. H -NHCOOC2H4OCH3 do. -C2H4CN red 31 do. H -NHSO2CH3 do. do. do.
32 do. H -NHCOC2H4Cl do. do. do.
TABLE (cont.)
Ex. - Shade on polyester Oo 33 -OH3 H z -OH2OH=OHOI -O2H4SON red 34 L > do. C) O L -O P 0 (o 37 do. do. do. -OH2OH=OHOI do. do.
I I, G IN IN do. do. do. do.
n I I I I oo"o"o" o" U H ~ ci 41 V I O O OOI O 0 0, 0, 3, -n0 On 8 8 03 0, oO 8 III I I I I I I I ii C 43 r H do. do. do. do.
I G Q X n n n x n n O n X I aN I I I a: OK o Un x o s co a) o Sz X X X e X X X * t t t .
TABLE (cont.)
Ex. Shade on polyester No. R1 R2 R3 R4 R5 fibres 44 -CH3 -OCH3 -NHCOCH3 -CH3C#CH -C2H4CN violet 45 do. -CH3 do. -CH2CH=CH2 do. red 46 do. do. do. -CH2CH=CHCl do. do.
47 do. do. do. do. H do.
48 do. Cl do. -CH2CH=CH2 -CH2CH=CH2 do.
49 do. do. do. do. H do.
50 do. H -NHCOOC2H4OC2H5 -CH2CH=CHCl -C2H4CN do.
51 do. H -NHCOCHClCH3 do. do. do.
52 do. H -NHCOCHOHCH3 do. do. do.
53 do. H -NHCOCHBrCH3 do. do. do.
54 do. H -NHCOCH2CH3Br do. do. do.
55 do. H -NHCOOCH2C6H5 do. do. do.
56 do. H -NHCOCH2OC6H5 do. do. do.
57 do. H -NHCOCH2C6H5 do. do. do.
58 do. H -NHCOCH2OCH2CH3 do. do. do.
59 do. H -NHCOCH3 -CH(CH3)-C#CH -C2H4COOC2H5 do.
TABLE (cont.)
Ex. Shade on polyester No. R1 R2 R3 R4 R5 fibres 60 -CH2 H -NHCOCH3 -CH(CH3-C#CH -C2H4CN red 61 do. H do. -CH2-CBr=CH2 do. do.
62 do. H do. -CH2-CCl=CH2 do. do.
63 do. H do. -CH2C#CH -CH2C=CH do.
64 do. H do. -CH2C(CH3)=CH2 -CH2C(CH3)=CH2 do.
65 do. H do. -CH2CBr=CH2 -CH2CBr=CH2 do.
66 do. -OCH2 do. -CH2CH=CHCl H violet 67 do. H do. do. -C2H4OCOC2H5 rot 68 do. H do. do. -C2H4OCONHC2H5 do.
69 do. H do. do. -C2H4CONH2 rot 70 do. H do. do. -C2H5 violet 71 do. H do. do. -C2H4OCH3 do.
72 do. H do. do. -C2H4OC2H5 do.
73 do. H do. do. -C2H4OCH2CH=CH2 do.
74 do. H CH2 do. do. rot 75 do. H do. do. -C2H4OCH3 do.
76 do. H do. do. -C2H5 do.
TABLE (cont.)
Ex. Shade on polyester No. R1 R2 R3 R4 R5 fibres 77 -CH3 H H -CH2CH=CHCl -C2H5 orange 78 do. H H do. -C2H4OCH3 do.
79 do. H -NHCOCH3 do. -C2H4OCH2C6H5 violet 80 do. H do. do. -C2H4Cl red 81 do. H do. do. -C2H4Br do.
82 do. H do. do. -C2H4OH violet 83 do. H do. do. -C2H4OCH2C#CH do.
84 -C2H5 H do. do. -C2H4CONH2 red 85 CH3 H do. do. -CH2CH(CH3)O-COCH3 do.
86 CH3 H -NHCOCH2OCH2C6H5 do. do. do.
5 10
15 20 25 30 35 40 45 50
APPLICATION EXAMPLE
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 3 parts sodium laurylsulphate in 4000 parts water. 100 Parts polyester fibre is added to the bath at 40 to 500 and 20 parts of a chlorinated benzene dispersed in water is added thereto. The bath is slowly heated to 1000 and dyeing is effected for 1 to 2 hours at 95 to 1000. The red dyed fibre is washed, soaped, washed again and dried. An even dyeing with good fastness is obtained.
Claims (22)
1. A compound of formula 1,
in which R, is (C1-4)alkyl optionally mono-substituted by chlorine, bromine, cyano, hydroxy,
(C1-2)alkoxy, (C1~2)alkoxycarbonyl or phenyl: or phenyl optionally substituted by up to two
substituents selected from the group consisting of chlorine, bromine, methyl and
(C1-2)alkoxy,
K is a radical of the 1 4-phenylene series, and
A is a secondary or tertiary amino group which contains an unsaturated aliphatic radical.
2. A compound according to Claim 1, in which the radical -K-A is of formula
in which R2 is hydrogen, chlorine, bromine, (C1-2) alkyl or (C1-2)alkoxy,
R3 is hydrogen, methyl or acylamino,
R4 is (C3~4)alkynyl; or (C3-4)alkenyl optionally monosubstituted by chlorine, bromine, or phenyl,
R5 is hydrogen; (C3~4)alkynyl; (C3-4)alkenyl optionally monosubstituted by chlorine, bromine, or
phenyl;; (CI~3)alkyl optionally monosubstituted by chlorine, bromine, hydroxy, cyano, thiocyano,
(C1-3)alkoxy, (C3-4)alkenyloxy, (C3-4)alkynyloxy, formyloxy, alkyl(C1-3)carbonyloxy, alkoxy(C1~3)carbonyl, alkoxy(C13)carbonyIoxy, chloro- or bromo-alkyl(C1-2)carbonyloxy,
benzyloxy, phenyl, phenoxy, phenyI(C12)alkoxy, aminocarbonyl, aminocarbonyloxy, (C1-3)-
alkyl- or di(CI~3)alkyl-amino-carbonyl or - carbonyloxy or phenylaminocarbonyl or
carbonyloxy; (C5-7)cycloalkyl optionally substituted by up to three methyl groups; or phenyl
optionally substituted by up to two substituents selected from the group consisting of chlorine,
bromine, methyl and (C1-2)alkoxy.
3. A compound according to Claim 2, in which F3 is R3, where R3' is hydrogen; methyl; alkyl(C1-2)- carbonylamino; benzoylamino; (C1-2)alkoxycarbonylamino; benzyloxycarbonylamino; hydroxychloro-, bromo-, (C1-2)alkoxy-, phenyl-, phenoxy- or benzyloxy-alkyl(C1-2)carbonylamino; 2 (C1-2)alkoxyethoxycarbonylamino; or methylsulphonylamino.
4. A compound according to any one of Claims 1 to 3 in which F1 is R,, where R1' is (C1-3)alkyl; or phenyl optionally substituted by up to two substituents selected from chlorine, bromine, methyl and (C1-2)alkoxy.
5. A compound according to any one of Claims 2 to 4, in which R2 is F2,, where R2 is hydrogen, methyl, chlorine or (C1-2)alkoxy.
6. A compound according to Clams 2 to 5, in which R4 is R4', where R4' is (C3-4)alkynyl; or (C3-4)alkenyl optionally monosubstituted by chlorine or bromine.
7. A compound according to Claims 2 to 6, in which R5 is R5, where R5' is hydrogen, (C3~4)-alkynyl; (C3~4)alkenyl optionally monosubstituted by chlorine or bromine; (C1-3)alkyl optionally monosubstituted by chlorine, bromine, hydroxyl, cyano, thiocyano, allyloxy, benzyloxy, propynyloxy, alkyl(C1-2)carbonyloxy, alkoxy(C1-2)carbonyl, alkoxy(C1-2)carbonyloxy, (C1-2)alkoxy, phenyl, aminocarbonyl, (C1-2)alkylaminocarbonyloxy or phenylaminocarbonyloxy.
8. A compound according to any one of Claims 2 to 7, in which R2 is hydrogen or (C1-2)alkoxy,
9. A compound according to any one of Claims 2 to 8, in which R3 is alkyl(C1-2)carbonylamino.
10. A compound according to any one of Claims 2 to 9, in which R4 is Razz where R'4 is allyl, 3chloroallyl or-2-methylallyl.
11. A compound according to any one of Claims 2 to 10, in which R5 is Razz where R'5 is allyl, 3chloroally, 2-methylallyl, cyanoethyl, alkyl(C,~2)carbonyloxyethyl alkoxy(C1~2)carbonylethyl or benzyl, with cyanoethyl, acetoxyethyl and al koxy(C1 2)carbonylethyl.
12. A compound according to any one of Claims 2 to 1 in which R2 is hydrogen.
13. A compound according to any one of Claims 2 to 12, in which R, is methyl, R2 is hydrogen, R3 is alkyl(C1~2)carbonylamino, R4 is 3-chloroallyl and R5 cyanoethyl, acetoxyethyl or alkoxy(C1-2)carbonylethyl.
14. A compound of formula
15. A compound according to any one of Examples 2 to 86.
1 6. A process for the production of a compound of formula I, as defined in Claim 1, comprising coupling a diazotized amine of formula II,
in which R, is as defined in Claim 1, with an amine of formula III H - K-A III in which K and A are as defined in Claim 1.
1 7. A process for the production of a compound of formula I, as defined in Claim 1 substantially as hereinbefore described with reference to any one of Examples 1 to 86.
18. A compound of formula I, as defined in Claim 1, whenever obtained by a process according to
Claim 16 or Claim 17.
19. A process for dyeing or printing textile substrates consisting of or comprising synthetic or semi-synthetic, hydrophobic, high molecular weight organic materials comprising applying a compound according to any one of Claims 1 to 15 or 18, thereto as dyestuff.
20. A process according to Claim 19, in which the substrate consists of or comprises linear, aromatic polyesters, cellulose 2 acetate, cellulose triacetate or synthetic polyamide.
21. A process for dyeing or printing textile substrates comprising synthetic or semi-synthetic, hydrophobic, high molecular weight organic materials substantially as hereinbefore described with reference to the Application Example.
22. Dyed or printed substrate whenever obtained by a process according to any one of Claims 19 to 21.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH88879A CH638549A5 (en) | 1979-01-30 | 1979-01-30 | AZO CONNECTIONS. |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| GB2041391A true GB2041391A (en) | 1980-09-10 |
| GB2041391B GB2041391B (en) | 1982-11-17 |
Family
ID=4197515
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB8002572A Expired GB2041391B (en) | 1979-01-30 | 1980-01-25 | Mono azo dyes |
Country Status (10)
| Country | Link |
|---|---|
| JP (1) | JPS55102655A (en) |
| KR (1) | KR830001915A (en) |
| BR (1) | BR8000554A (en) |
| CA (1) | CA1133473A (en) |
| CH (1) | CH638549A5 (en) |
| DE (1) | DE3001945A1 (en) |
| ES (1) | ES8101637A1 (en) |
| FR (1) | FR2447954A1 (en) |
| GB (1) | GB2041391B (en) |
| IT (1) | IT8047723A0 (en) |
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0039054A1 (en) * | 1980-04-28 | 1981-11-04 | CASSELLA Aktiengesellschaft | Water-insoluble azo dyes, process for their production and their application |
| EP0087677A1 (en) * | 1982-02-27 | 1983-09-07 | BASF Aktiengesellschaft | Isothiazolazo dyestuffs |
| EP0151287A3 (en) * | 1984-01-07 | 1985-09-25 | Basf Aktiengesellschaft | Isothiazole azodyes |
| EP0156216A1 (en) * | 1984-03-14 | 1985-10-02 | BASF Aktiengesellschaft | Isothiazole azo dyestuffs |
| US4764600A (en) * | 1982-02-16 | 1988-08-16 | Basf Aktiengesellschaft | Isothiazolylazo dyes having aminophenyl and aminonaphthyl components |
| EP0344487A3 (en) * | 1988-05-17 | 1990-01-17 | Basf Aktiengesellschaft | Azo dyes of the 5-aminoisothiazole series |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3036576A1 (en) | 1980-09-27 | 1982-05-19 | Cassella Ag, 6000 Frankfurt | WATER-INSOLUBLE AZO DYE, METHOD FOR THE PRODUCTION AND USE THEREOF |
| JPS60155269A (en) * | 1984-01-24 | 1985-08-15 | Sumitomo Chem Co Ltd | isothiazole azo dye |
| KR100711762B1 (en) * | 2005-07-15 | 2007-04-30 | 주식회사 포스코 | Pelletizer for Fine Powder Assembly |
-
1979
- 1979-01-30 CH CH88879A patent/CH638549A5/en not_active IP Right Cessation
-
1980
- 1980-01-21 DE DE19803001945 patent/DE3001945A1/en not_active Withdrawn
- 1980-01-25 GB GB8002572A patent/GB2041391B/en not_active Expired
- 1980-01-28 CA CA344,554A patent/CA1133473A/en not_active Expired
- 1980-01-28 IT IT8047723A patent/IT8047723A0/en unknown
- 1980-01-29 FR FR8001849A patent/FR2447954A1/en active Granted
- 1980-01-29 BR BR8000554A patent/BR8000554A/en unknown
- 1980-01-29 KR KR1019800000319A patent/KR830001915A/en not_active Ceased
- 1980-01-29 JP JP841980A patent/JPS55102655A/en active Pending
- 1980-01-30 ES ES488376A patent/ES8101637A1/en not_active Expired
Cited By (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0039054A1 (en) * | 1980-04-28 | 1981-11-04 | CASSELLA Aktiengesellschaft | Water-insoluble azo dyes, process for their production and their application |
| US4440681A (en) * | 1980-04-28 | 1984-04-03 | Cassella Aktiengesellschaft | Water-insoluble monoazo dyestuffs and their preparation |
| US4764600A (en) * | 1982-02-16 | 1988-08-16 | Basf Aktiengesellschaft | Isothiazolylazo dyes having aminophenyl and aminonaphthyl components |
| US4960874A (en) * | 1982-02-16 | 1990-10-02 | Basf Aktiengesellschaft | Isothiazolylazo dyes having aminophenyl and aminonaphthyl components |
| EP0087677A1 (en) * | 1982-02-27 | 1983-09-07 | BASF Aktiengesellschaft | Isothiazolazo dyestuffs |
| US4496480A (en) * | 1982-02-27 | 1985-01-29 | Basf Aktiengesellschaft | Isothiazolazo dyes having coupling components which are free from unsaturated aliphatic radicals |
| EP0151287A3 (en) * | 1984-01-07 | 1985-09-25 | Basf Aktiengesellschaft | Isothiazole azodyes |
| EP0156216A1 (en) * | 1984-03-14 | 1985-10-02 | BASF Aktiengesellschaft | Isothiazole azo dyestuffs |
| US4619992A (en) * | 1984-03-14 | 1986-10-28 | Basf Aktiengesellschaft | 3-(β-aminoethyl)-4-cyano-isothiazolylazo dyes |
| EP0344487A3 (en) * | 1988-05-17 | 1990-01-17 | Basf Aktiengesellschaft | Azo dyes of the 5-aminoisothiazole series |
Also Published As
| Publication number | Publication date |
|---|---|
| DE3001945A1 (en) | 1980-08-07 |
| IT8047723A0 (en) | 1980-01-28 |
| FR2447954A1 (en) | 1980-08-29 |
| FR2447954B1 (en) | 1983-11-25 |
| GB2041391B (en) | 1982-11-17 |
| ES488376A0 (en) | 1980-12-16 |
| CA1133473A (en) | 1982-10-12 |
| CH638549A5 (en) | 1983-09-30 |
| KR830001915A (en) | 1983-05-19 |
| JPS55102655A (en) | 1980-08-06 |
| ES8101637A1 (en) | 1980-12-16 |
| BR8000554A (en) | 1980-10-21 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PCNP | Patent ceased through non-payment of renewal fee |