GB2034733A - Azo dyes - Google Patents
Azo dyes Download PDFInfo
- Publication number
- GB2034733A GB2034733A GB7931821A GB7931821A GB2034733A GB 2034733 A GB2034733 A GB 2034733A GB 7931821 A GB7931821 A GB 7931821A GB 7931821 A GB7931821 A GB 7931821A GB 2034733 A GB2034733 A GB 2034733A
- Authority
- GB
- United Kingdom
- Prior art keywords
- hydrogen
- dye
- unsubstituted
- substituted
- chlorine
- 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.)
- Withdrawn
Links
- 239000000987 azo dye Substances 0.000 title claims abstract description 6
- -1 nitro- Chemical class 0.000 claims abstract description 39
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 23
- 239000001257 hydrogen Substances 0.000 claims abstract description 21
- 239000000975 dye Substances 0.000 claims abstract description 18
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 13
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims abstract description 9
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 8
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 7
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims abstract description 6
- 239000000460 chlorine Substances 0.000 claims abstract description 6
- 238000004043 dyeing Methods 0.000 claims abstract description 6
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims abstract description 5
- 229910052801 chlorine Inorganic materials 0.000 claims abstract description 5
- 125000004076 pyridyl group Chemical class 0.000 claims abstract description 5
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 4
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 4
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims abstract description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 4
- 239000001301 oxygen Substances 0.000 claims abstract description 4
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 4
- 125000001424 substituent group Chemical group 0.000 claims abstract description 4
- 125000002130 sulfonic acid ester group Chemical group 0.000 claims abstract description 4
- 125000001931 aliphatic group Chemical group 0.000 claims abstract description 3
- 125000003118 aryl group Chemical group 0.000 claims abstract description 3
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims abstract description 3
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims abstract description 3
- 229910052794 bromium Inorganic materials 0.000 claims abstract description 3
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims abstract description 3
- 239000008199 coating composition Substances 0.000 claims abstract description 3
- 125000002541 furyl group Chemical class 0.000 claims abstract description 3
- 125000000623 heterocyclic group Chemical group 0.000 claims abstract description 3
- 239000010985 leather Substances 0.000 claims abstract description 3
- 125000001624 naphthyl group Chemical class 0.000 claims abstract description 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 3
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims abstract description 3
- 125000000286 phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 claims abstract description 3
- 125000001544 thienyl group Chemical class 0.000 claims abstract description 3
- 239000003960 organic solvent Substances 0.000 claims abstract 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 11
- 238000000034 method Methods 0.000 claims description 9
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 9
- 230000008878 coupling Effects 0.000 claims description 7
- 238000010168 coupling process Methods 0.000 claims description 7
- 238000005859 coupling reaction Methods 0.000 claims description 7
- 239000000203 mixture Substances 0.000 claims description 4
- 150000001412 amines Chemical class 0.000 claims description 3
- 150000001989 diazonium salts Chemical class 0.000 claims description 3
- 229920002994 synthetic fiber Polymers 0.000 claims description 2
- 239000012209 synthetic fiber Substances 0.000 claims description 2
- 238000009472 formulation Methods 0.000 claims 2
- 239000000470 constituent Substances 0.000 claims 1
- 239000000463 material Substances 0.000 claims 1
- 238000002360 preparation method Methods 0.000 claims 1
- 229920001169 thermoplastic Polymers 0.000 claims 1
- 239000004416 thermosoftening plastic Substances 0.000 claims 1
- 229920000728 polyester Polymers 0.000 abstract description 4
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 abstract description 3
- 239000004744 fabric Substances 0.000 abstract description 2
- 150000002431 hydrogen Chemical group 0.000 abstract 2
- 150000003254 radicals Chemical class 0.000 description 12
- FFRBMBIXVSCUFS-UHFFFAOYSA-N 2,4-dinitro-1-naphthol Chemical compound C1=CC=C2C(O)=C([N+]([O-])=O)C=C([N+]([O-])=O)C2=C1 FFRBMBIXVSCUFS-UHFFFAOYSA-N 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 4
- 125000004432 carbon atom Chemical group C* 0.000 description 4
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 3
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 3
- QUPDWYMUPZLYJZ-UHFFFAOYSA-N ethyl Chemical compound C[CH2] QUPDWYMUPZLYJZ-UHFFFAOYSA-N 0.000 description 3
- 239000000835 fiber Substances 0.000 description 3
- WPWHSFAFEBZWBB-UHFFFAOYSA-N 1-butyl radical Chemical compound [CH2]CCC WPWHSFAFEBZWBB-UHFFFAOYSA-N 0.000 description 2
- RFONJRMUUALMBA-UHFFFAOYSA-N 2-methanidylpropane Chemical compound CC(C)[CH2-] RFONJRMUUALMBA-UHFFFAOYSA-N 0.000 description 2
- 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 description 2
- RXQNKKRGJJRMKD-UHFFFAOYSA-N 5-bromo-2-methylaniline Chemical compound CC1=CC=C(Br)C=C1N RXQNKKRGJJRMKD-UHFFFAOYSA-N 0.000 description 2
- 229920000742 Cotton Polymers 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 229960000583 acetic acid Drugs 0.000 description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 238000006193 diazotization reaction Methods 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
- 239000012362 glacial acetic acid Substances 0.000 description 2
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 125000000963 oxybis(methylene) group Chemical group [H]C([H])(*)OC([H])([H])* 0.000 description 2
- 125000005592 polycycloalkyl group Polymers 0.000 description 2
- 239000000992 solvent dye Substances 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- 229920003043 Cellulose fiber Polymers 0.000 description 1
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 1
- 239000004952 Polyamide Substances 0.000 description 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 229940040526 anhydrous sodium acetate Drugs 0.000 description 1
- LFZDEAVRTJKYAF-UHFFFAOYSA-L barium(2+) 2-[(2-hydroxynaphthalen-1-yl)diazenyl]naphthalene-1-sulfonate Chemical compound [Ba+2].C1=CC=CC2=C(S([O-])(=O)=O)C(N=NC3=C4C=CC=CC4=CC=C3O)=CC=C21.C1=CC=CC2=C(S([O-])(=O)=O)C(N=NC3=C4C=CC=CC4=CC=C3O)=CC=C21 LFZDEAVRTJKYAF-UHFFFAOYSA-L 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- 125000004181 carboxyalkyl group Chemical group 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 229920001778 nylon Polymers 0.000 description 1
- 125000006353 oxyethylene group Chemical group 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 125000003884 phenylalkyl group Chemical group 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- 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 1
- STZCRXQWRGQSJD-UHFFFAOYSA-N sodium;4-[[4-(dimethylamino)phenyl]diazenyl]benzenesulfonic acid Chemical compound [Na+].C1=CC(N(C)C)=CC=C1N=NC1=CC=C(S(O)(=O)=O)C=C1 STZCRXQWRGQSJD-UHFFFAOYSA-N 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 125000005346 substituted cycloalkyl group Chemical group 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
- C09B29/34—Monoazo dyes prepared by diazotising and coupling from other coupling components
- C09B29/36—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds
- C09B29/3604—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds containing only a nitrogen as heteroatom
- C09B29/3617—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds containing only a nitrogen as heteroatom containing a six-membered heterocyclic with only one nitrogen as heteroatom
- C09B29/3621—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds containing only a nitrogen as heteroatom containing a six-membered heterocyclic with only one nitrogen as heteroatom from a pyridine ring
- C09B29/3639—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds containing only a nitrogen as heteroatom containing a six-membered heterocyclic with only one nitrogen as heteroatom from a pyridine ring from a pyridine ring containing one or more amino groups
-
- 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
- C09B29/0011—Monoazo dyes prepared by diazotising and coupling from diazotized anilines from diazotized anilines directly substituted by a heterocyclic ring (not condensed)
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Developing Agents For Electrophotography (AREA)
- Plural Heterocyclic Compounds (AREA)
- Coloring (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Novel azo dyes have the general formula <IMAGE> where A is cyano or carbamyl, R is hydrogen, alkyl or phenyl, R<1> is hydrogen, bromine, chlorine or nitro, X is a sulfonic acid ester group or unsubstituted or substituted sulfamyl, R<3> is hydrogen or a C1-C8-alkyl which may or may not be interrupted by oxygen and is unsubstituted or substituted by hydroxyl, C1-C8- alkoxy or phenoxy, or is benzyl, phenylethyl or cyclohexyl, or is unsubstituted or chlorine-, bromine-, nitro-, methyl-, ethyl-, phenoxy- or di-C1-C4-alkylamino-substituted phenyl, naphthyl, pyridyl, thienyl or furyl, the substituents B<1> independently of one another are hydrogen or an aliphatic, cycloaliphatic, araliphatic, aromatic, heterocyclic or acyl radical, and B<2> is hydrogen or an aliphatic radical. The dyes according to the invention are outstandingly suitable for dyeing polyesters, cellulosic fabrics, leather, coating compositions and organic solvents.
Description
SPECIFICATION
Azo dyes
The present invention relates to azo dyes. The azo dyes of the invention are compounds of the general formula I
where
A is cyano or carbamyl,
R is hydrogen, alkyl or phenyl,
R1 is hydrogen, bromine, chlorine or nitro,
X is a sulfonic acid ester group or unsubstituted or substituted sulfamyl,
R3 is hydrogen or a C1-C8-alkyl which may or may not be interrupted by oxygen and is
unsubstituted or substituted by hydroxyl, C1-C8-alkoxy or phenoxy, or is benzyl, phenylethyl or
cyclohexyl, or is unsubstituted or chlorine-, bromine-, nitro-, methyl-, ethyl-, phenoxy- or di-C1-C4-
alkylamino-substituted phenyl, naphthyl, pyridyl, thienyl or furyl,
the substituents B' independently of one another are hydrogen or an aliphatic, cycloaliphatic, araliphatic, aromatic, heterocyclic or acyl radical and
B2 is hydrogen or an aliphatic radical.
Examples of alkyl R are radicals of 1 to 6 carbon atoms, particularly methyl, ethyl, propyl, butyl and pentyl.
Examples of radicals X are sulfonic acid aryl ester groups, and sulfamyl which is monosubstituted or disubstituted by C1-C8-alkyl, by alkoxy-, polyalkoxy-, phenoxy-, phenoxyalkoxy- or benzyloxysubstituted C2-C3-alkyl, by phenyl-C1-C4-alkyl, by cyclohexyl or by unsubstituted or methyl-, ethyl-, methoxy-, ethoxy-, chlorine- or bromine-substituted phenyl.
Specific examples of radicals X are:
SO2OT; T=C6H5, C6H4Cl, C6G4CH3, C6H4OCH3 or C6H3(CH3)2 SO2T1; T' = NHCH3, NHC2H5, NHC3H7, NHC4Hg, NHC6H,3, NHC8H17,
NHC2H4OCH3, NHC2H4OC2H5, NHC2H4OC4H9, NHC2H40C2H40CH3, NHC2H4OC2H4O04H9, NH(CH2)3,
NH(CH2)3OCH3, NH(CH2)3OC2H4OC2H5, NH(CH2)3OC9H7, NH(CH2)3OC4H9, NH(CH3)2OC2H4OCH3,
NH(CH2)3OC2H4OC4H9, NH(CH2)3OC2H4OC6H5, NH(CH2)3OC2H4OCH2C6H5, the corresponding disubstituted radicals, in which the radicals T1 may differ from one another, and NHCH2C6Hs, NHC2H4C6Hs,
NHC6H11, NHC6Hs, NHC6H4CH3, NHC6H4C2H5, NHC6H4OCH3, NHC6H4CI, NHC6H3(CH3)2,
Preferred radicals X are the sulfonic acid ester groups and di-C1-C4-aikyl-substituted or monoaryl-substituted sulfamyl.
Radicals B1 are for example, independently of one another, hydrogen, methyl, C2-C8-alkyl which may or may not be interrupted by ether oxygen and is unsubstituted or substituted by hydroxyl, C1-C8- alkoxy, benzyloxy, p-phenylethoxy, phenoxy, tolyloxy, cyclohexyloxy or cyano, C9-C18-alkyl, C5-C8- cycloalkyl, hydroxycyclohexyl, p-hydroxyethoxycyclohexyl, C7-C12-polycycloalkyl, hydroxynorbornyl, hydroxymethylnorbornyl, hydroxyethylnorbornyl, ch loromethylnorbornyl, phenylalkyl or tolylalkyl, where alkyl is of 1 to 4 carbon atoms, unsubstituted or chlorine-, hydroxy-, methoxy-, ethoxy-, methyl-, ethylor hydroxyethoxy-substituted phenyl, allyl, pyrrolidonylalkyl, where alkyl is of 2, 3, 4 or 6 carbon atoms, carboxyalkyl, where alkyl is of 2 to 5 carbon atoms,
Examples of B2 are the same as the aliphatic radicals mentioned for B1, and examples of R3, to the extent that the general definitions coincide, are also the same as for B1.
Specific examples of radicals B' and BZ, to the extent that they fall under the general definition, are, in addition to those already mentioned, 1. unsubstituted or substituted alkyl radicals:
CH3, C2H5, n- or i-C3H7, n- or i-C4H9, C6H13,
(CH2)2O(CH2)2OH, (CH2)30(CH2)4OH, (CH2)3OC2H4OH, (CH2)2CN, (CH2)5CN, (CH2)6CN, (CH2),CN, (CH2)2O(CH2)2CN, (CH2)3O(CH2)2CN, (CH2)20(CH2)20(CH2)2CN, (CH2)3OC2H40CH3, (CH2)3OC2H40C2H5, (CH2)3O(CH2)6OH, (CH2)3OC2H4OCH(CH3)2, (CH2)3OC2H4OC4H9, (CH2)3OC2H4OCH2C6H5, (C H2)3OC2H4OC2H4C6H5,
the corresponding radicals in which the group
occurs twice or three times,
CH2CH2OCH3, CH2CH2OC2H5, CH2CH2OC3H7, CH2CH2OC4H9, CH2CH2OC6H5, (CH2)3OCH3, (CH2)3OC2H5,
(CH2)3OC8H13, (CH2)3OC8H17, (CH2)3O-, (CH2)3OCH2C6H5, (CH2)3OC2H4C6H5, (CH2)3OC6H5,
2. unsubstituted or substituted cycloalkyl and polycycloalkyl radicals:
3. aralkyl radicals:
as well as the corresponding radicals containing C6H4CH3 in place of C6Hs; 4. unsubstituted or substituted phenyl radicals: C6H5, C6H4CH3, C6H3(CH3)2, C6H4OCH3, C6H40C2Hs, C6H40H,
5.
CH2CH-CH2, (CH2)2COOH, (CH2)5COOH and
where n is 2, 3,4 or 6,
C2H4OCOCH3, C2H4OCHO, C2H4OCOCH3, (C2H4O)2COCH3, (C2H4O)2CHO, (CH2)3OCOCH3, (CH2)3OCHO,
and C2H40COC2H4COOH.
Examples of preferred substituents B' and 82 are hydrogen, CH3, C2H5, n- or i-C3H7, n- or i-C4H9,
C6H13, CH2CH2OH, (CH2)3OH,
(CH2)2O(CH2)2OH, (CH2)3O(CH2)2OH, (CH2)3O(CH2)4OH,
CH2CH2OCH3, CH2CH2OC2H5, CH2CH2OC4H9, (CH2)3OCH3, (CH2)3OC2H5, (CH2)3OC3H7, (CH2)3OC4H9,
Examples of radicals
are pyrrolidino, piperidino, morpholino and N-methylpiperazino.
Preferred diazo components are those set out in Table 1.
TABLE 1
Formula T R' R3 1 -N(C2H5)2 H 06H5 2 -N(C4H9) H C6H5 3 \ H -CH,-O-CH, A 4 -N O H -CH2-CH2-0-CH2-C6H5 P 5 -Ne H C6H5 6 -NOcH3 H C6Hs 7 -N-C1 H C6Hs 8 OC6H5 H CH5 9 3 H 06H3 10 -N(C,H,) Br 11 " Br CH2CH24C3H7 12 -N(C4H9) Br QH TABLE 1 (Continued)
Formula T Rl R3
13 -N(C4H9) Br -CH2-CH2O-C3H7 14 -N(C2H,) Br
15 H H 16 OC6Hs H
On cellulose fibers, natural polyamides, nylons, polyesters and other synthetic fibers, the dyes of the formula I give yellow to red dyeings having very good lightfastness, fastness to thermofixing and wetfastness. The deep colors and clear hues achievable with many of the dyes deserve particular mention. The dyes of the formula I are particularly suitable for the process described in German Patent 1,81 1,796, i.e. a process in which cellulosic fibers are contacted with water and an oxyethylene or oxypropylene compound to swell the fibers and, whilst the fibers are still swollen, with a dye according to the invention. Some of them may also be used as solvent dyes, for example for dyeing coating compositions, solvents or leather.
Dyes of particular industrial importance are those of the formula la
where
R4 is hydrogen or chlorine, Re is methyl, C1-C4-alkoxyethyl, phenoxyethyl, phenyl or pyridyl and
A, Bt, B2, X and R have the above meanings.
Preferably R is hydrogen or methyl and B2 is hydrogen. Another preferred combination is where R is H and A is CONY,.
The preferred meanings of B' are as stated earlier.
A dye of the formula I may be prepared by reacting a diazonium compound of an amine of the formula
with a coupling component of the formula
AR, R1, X, R3, B1 and B2 having the above meanings. The diazotization and coupling may be carried out by conventional methods.
In the Examples which follow, parts and percentages are by weight, unless stated otherwise.
EXAMPLE 1
32 parts of 40% strength nitrosylsulfuric acid are added to a solution of 30 parts of the compound of the formula1 in Table 1 in 1,500 parts by volume of glacial acetic acid and 200 parts of propionic acid at 0--50C, and the mixture is stirred at this temperature for 2 hours. Excess nitrosylsulfuric acid is then destroyed with urea. A solution of 27 parts of 2,6-bis-(2'-methoxyethylamino)-3-cyano-4methylpyridine in 500 parts of glacial acetic acid is then added to the diazotization mixture at 0--50C, followed by a total of 50 parts of anhydrous sodium acetate added gradually. After completion of coupling, the dye which has formed is filtered off, washed with ethanol and then with water, and dried at 1000. An orange powder is obtained, which gives an orange solution in N-methylpyrrolidone.On cotton or polyester or cotton/polyester union fabrics, this dye, used by the process described in German
Patent 1,81 1,796, gives strong orange hues with excellent fastness characteristics.
The following dyes may be obtained by similar methods:
Coupling component
Uiazo component Example from Table 1 R' R Hue 2 2 -(CH2)2-O-CH3 -(CH2)2-O-CH3 orange 3 4 ,, " orange 4 5 " p, orange 5 8 p, " reddish orange 6 12 p, " orange 7 1 (CHa)aOCH3 -( CH2)3O-CH orange 8 2 " p, orange 9 9 4 ,, pp orange 10 5 p, " orange 11 8 pp " bright red 12 9 ,1 13 1 -C4H, -C4H9 orange 14 2 p, 15 3 pp pp 16 5 pp " pp 17 6 p, pp p, 18 7 pp " "pp 19 8 " " bright red 20 9 p, pp 21 -CH2-CH2 -CH2-CH2 < ) , orange 22 1 -CH2-CH2-O-CH, H golden yellow 23 2 pp H p, 24 4 H H 25 1 -(CH2)J-O-(CH2)2-O- H yellowish orange Coupling component
Diazo component Example from Table 1 R1 R2 Hue 26 2 (CH2)3-o-(cH2)2-o < ) H yellowish orange 27 4 pp H orange 28 5 p, H p, 29 7 pp H pp 30 8 pp H o, 31 2 -(CH,),-O-CH, -(CH2)30-(CH2)2'0 32 8 pp " bright red 33 3 " " orange The following compounds are particularly suitable for use as solvent dyes:
Coupling component
Diazo component (as for Examples 2-33)
Example of Table 1 R1 @@ R2 Hue
34 18 -(CH2)3-O-(CH2)4-OH yellowish
orange
35 11 p, golden
yellow
36 12 p, yellowish
orange
37 13 " golden
yellow
38 14 " golden
yellow
39 15 " yellowish
orange
40 16 " reddish
orange
Example n X Y R1 = R2 Hue
41 3 NHC6H5 Br C2H4OH orange
42 3 " " C2H4OCH3 "
43 3 " " C3H6OCH3 "
44 3 " " C3H6OH "
45 3 " " C2H4OC2H4OH "
46 3 " " (CH2)3O(CH2)4OH "
47 4 " " C2H4OH "
48 4 " " C2H4OCH3 "
49 4 " " C2H4OC2H4OH "
50 4 " " C3H6OCH3 "
51 4 " Cl " "
52 4 " " C2H4OC2H4OH "
53 3 " " " "
54 3 OC6H5 " " "
55 3 " Br " "
56 3 " " C2H4OH "
57 3 " " C2H4OCH3 "
58 3 " H " "
59 3 " H C2H4OC2H4OH "
60 3 " Br (CH2)3O(CH2)4OH "
61 3 " " C3H2OCH3 "
62 3 " " C3H6OH "
63 4 " " C2H4OH "
64 4 " " C2H4OCH3 "
65 4 " " C2H4OC2H4OH "
66 4 " " " "
Claims (8)
1. An azo dye of the general formula
where
A is cyano or carbamyl,
R is hydrogen, alkyl or phenyl
R1 is hydrogen, bromine, chlorine or nitro,
X is a sulfonic acid ester group or unsubstituted or substituted sulfamyl,
R3 is hydrogen or a C,--C,-alkyl which may or may not be interrupted by oxygen and is unsubstituted or substituted by hydroxyl, C1-C8-alkoxy or phenoxy, or is benzyl, phenylethyl or cyclohexyl, or is unsubstituted or chlorine-, bromine-, nitro-, methyl-, ethyl-, phenoxy- or di-C1-C4- alkylamino-substituted phenyl, naphthyl, pyridyl, thienyl or furyl,
the substituents B1 independently of one another are hydrogen or an aliphatic, cycloaliphatic, araliphatic, aromatic, heterocyclic or acyl radical and
B2 is hydrogen or an aliphatic radical.
2. A dye as claimed in claim 1, wherein R, X, R3, B1 and B2 denote radicals individually identified hereinbefore as examples thereof.
3. A dye as claimed in claim 1, of the formula
where
R4 is hydrogen or chlorine, R6 is methyl, C1-C4-alkoxyethyl, phenoxyethyl, phenyl or pyridyl and
A, B', B2, X and R have the meanings given in claim 1.
4. A dye as claimed in claim 1 and identified in any of the foregoing Examples 1 to 66.
5. A process for the preparation of a dye as claimed in claim 1, wherein a diazonium compound of an amine of the formula
is reacted with a coupling component of the formula
A, R, R1, X, R3, B1 and B2 having the meanings given in claim 1.
6. A process as claimed in claim 5, wherein a diazonium compound of an amine listed in Table 1 hereinbefore is used.
7. A dye formulation for dyeing natural and synthetic fibers, which contains a dye as claimed in any of claims 1 to 4 or prepared by a process as claimed in claim 5 or 6 together with one or more conventional constituents for dye formulations for such purposes.
8. A process for the mass-dyeing of thermoplastics material or for dyeing leather, coating compositions or organic solvents wherein a dye as claimed in any of claims 1 to 4 or prepared by a process as claimed in claim 5 or 6 is used.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19782839905 DE2839905A1 (en) | 1978-09-14 | 1978-09-14 | AZO DYES |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB2034733A true GB2034733A (en) | 1980-06-11 |
Family
ID=6049372
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB7931821A Withdrawn GB2034733A (en) | 1978-09-14 | 1979-09-13 | Azo dyes |
Country Status (5)
| Country | Link |
|---|---|
| JP (1) | JPS5540783A (en) |
| DE (1) | DE2839905A1 (en) |
| FR (1) | FR2436163A2 (en) |
| GB (1) | GB2034733A (en) |
| IT (1) | IT1123565B (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| USD377875S (en) | 1994-10-20 | 1997-02-11 | President Office Furniture Ltd. | Leg support |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CH611324A5 (en) * | 1974-04-09 | 1979-05-31 | Basf Ag |
-
1978
- 1978-09-14 DE DE19782839905 patent/DE2839905A1/en not_active Withdrawn
-
1979
- 1979-09-03 FR FR7921988A patent/FR2436163A2/en active Pending
- 1979-09-07 IT IT25550/79A patent/IT1123565B/en active
- 1979-09-13 GB GB7931821A patent/GB2034733A/en not_active Withdrawn
- 1979-09-13 JP JP11679579A patent/JPS5540783A/en active Pending
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| USD377875S (en) | 1994-10-20 | 1997-02-11 | President Office Furniture Ltd. | Leg support |
Also Published As
| Publication number | Publication date |
|---|---|
| FR2436163A2 (en) | 1980-04-11 |
| JPS5540783A (en) | 1980-03-22 |
| IT7925550A0 (en) | 1979-09-07 |
| IT1123565B (en) | 1986-04-30 |
| DE2839905A1 (en) | 1980-04-03 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US2832764A (en) | Production of azo dyestuffs | |
| US4097475A (en) | Disperse mono- and bisazo dyes derived from 2-amino-4,5-dicyanoimidazole | |
| US3407189A (en) | Water-insoluble monoazo dyestuffs | |
| US3939093A (en) | Daylight fluorescent pigments | |
| EP0047881B1 (en) | Dimethine compounds of the coumarine series, process for their preparation and their use as luminescent dyestuffs | |
| DE2121524A1 (en) | Disperse dyes made from o-phthalonitrile | |
| US3178405A (en) | Water-insoluble monoazo dyestuffs | |
| US4055556A (en) | Monoazo and disazo compounds having optionally further substituted 2-acyl-, carboxy- or cyano-benzothienyl diazo component radicals | |
| US4220586A (en) | Hetero-aryl azo acylamino substituted aceto-acetarylide pigments | |
| CH639119A5 (en) | AZOPIGMENTS. | |
| US4231746A (en) | Dyeing of cellulose-containing textile material and novel dyes for use therein | |
| US4424156A (en) | Halo-substituted amino-and substituted-sulphonamido-containing azo dyestuffs | |
| US3069408A (en) | Water-insoluble azo dyestuffs | |
| GB2034733A (en) | Azo dyes | |
| DE1644260A1 (en) | Process for the preparation of mono- and disazo dyes which are sparingly soluble in water | |
| US4065447A (en) | Azo compounds having a 3-arylthio- or aliphaticthio-4-cyano- or alkoxycarbonyl-pyrazolyl-5 diazo component radical | |
| US4077953A (en) | Tri-dentate metal complex azo pigments | |
| US2195787A (en) | Complex metal compounds of azo | |
| US4210583A (en) | Azo dyes of the 2,6-di(substituted) amino pyridine series | |
| US3963431A (en) | Method of dyeing with dispersible azo anilino dyestuffs | |
| US4042611A (en) | Water-in-soluble disazo methine compounds | |
| US4424154A (en) | Azo dye having a 3-cyano- or 3-carbamoyl-2,6-diaminopyridine coupling component | |
| DE2022624B2 (en) | Basic disazo dye, process for its preparation and its use | |
| US3157632A (en) | Water-insoluble monoazo-dyestuffs and process for preparing them | |
| US4097484A (en) | Mixed complexes of methine dyes |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| WAP | Application withdrawn, taken to be withdrawn or refused ** after publication under section 16(1) |