GB2113702A - Azo dyes - Google Patents

Azo dyes Download PDF

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GB2113702A
GB2113702A GB08200914A GB8200914A GB2113702A GB 2113702 A GB2113702 A GB 2113702A GB 08200914 A GB08200914 A GB 08200914A GB 8200914 A GB8200914 A GB 8200914A GB 2113702 A GB2113702 A GB 2113702A
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alkyl
alkoxy
substituted
halogen
cyano
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GB2113702B (en
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Dr Robert Nicholas Gourley
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Kodak Ltd
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Kodak Ltd
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
    • C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
    • C07D409/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
    • C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
    • C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
    • C07D333/26—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D333/42—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms with nitro or nitroso radicals directly attached to ring carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
    • C07D413/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
    • 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
    • C09B29/0059—Monoazo dyes prepared by diazotising and coupling from diazotized amino heterocyclic compounds the heterocyclic ring containing only sulfur as heteroatom
    • 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
    • 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
    • C09B29/0821—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 SH, SR, SO2R, SO2XR, SO2N
    • 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
    • C09B29/0832—Amino benzenes free of acid groups characterised by the amino group substituted amino group further substituted alkylamino, alkenylamino, alkynylamino, cycloalkylamino aralkylamino or arylamino having -N-alkylene-heterocyclic ring
    • 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
    • C09B29/3643—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 quinolines or hydrogenated quinolines
    • 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
    • C09B29/3686—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds containing nitrogen and oxygen as heteroatom

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  • Organic Chemistry (AREA)
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Abstract

Azo dyes giving bright blue shades on synthetic fibres have the formula: <IMAGE> where R indicates the possible presence of 1-3 substituents selected from a specified range and C' represents an aniline, tetrahydroquinoline or benzomorpholine coupler residue, and are prepared the corresponding acetyl substituted thiophene derivative with benzaldehyde, which may be optionally substituted.

Description

SPECIFICATION Azo dyes This invention relates to new azo dyes prepared frodm 2-amino-3-nitro-5-cinnamoylthiophene corn pounds. These dyes give bright blue shades, for example, on polyester, acetate and other synthetic fibers and exhibit improvements in one or more of such properties as bathochromic shift, fastness to light, sublimation, chlorine, heat, ozone, gas, perspiration, crock, and wash, build, pH stability, bloom resistance, depth of shade, leveling, strike rate and migration.
The new azo compounds have the formula:
wherein R is hydrogen or one to three substituents, which may be the same or different, selected from alkyl, hydroxy, alkoxy, halogen, nitro, carboxy, alkoxycarbonyl, alkanoylcarbonyl, alkanoyl, cyano, alkylamino, dialkylamino, and alkyl substituted with 1-3 of halogen, alkoxy, alkanoyl, alkanoyloxy, alkoxyca rbonyl, alkanoylamino, cya no, nitro, carbamoyl, alkylcarbamoyl, sulfamoyl and alkylsulfamoyl, and C' represents an aniline, tetrahydroquinoline or benzomorpholine coupling component which may be extensively substituted.
While our invention relates broadly to the new azo dyes having the above formula, it relates more particularly to those wherein R is hydrogen, halogen, alkyl, alkoxycarbonyl, hydroxy, nitro, alkoxy, alkanoyl, cyano, alkylamino and dialkylamino.
The coupler C more specifically has the formula:
wherein R1 and R2 are each selected from hydrogen, fluorine, chlorine, bromine, alkyl, cycloalkyl, alkoxy, phenoxy, alkylthio, arylthio, and radicals having the formula -NH-X-Pr9 in which X is -CO-, -COO-, or SO2 and R9 is selected from alkyl and alkyl substituted with halogen, hydroxy, phenoxy, aryl, cyano, cycloalkyl, alkylsulfonyl, alkylthio, alkanoyloxy, and alkoxy, and when X is -CO-, R9 also can be hydrogen, amino, alkenyl, alkylamino, dialkylamino, arylamino, aryl, orfuryl; R3 and R4 are selected from hydrogen; cycloalkyl; cycloalkyl substituted with one or two groups selected from alkyl; -OH, alkoxy, halogen and hydroxy substituted alkyl; phenyl or phenyl substituted with alkyl, alkoxy, halogen, alkanoylamino, cyano or alkoxycarbonyl; straight or branched alkenyl; straight or branched alkyl and such alkyl substituted with 1-3 of the followinq: hydroxy, halogen; cyano; amino; alkoxy; hydroxyalkoxy; succinimido; glutarimido; phenylcarbamoyloxy; phthalimido; phthalimidino; 2-pyrrolidono; cyclohexyl; phenoxy; phenyl or phenyl substituted with alkyl, alkoxy, halogen, alkanoylamino, cyano or alkoxycarbonyl; alkanoylamino; sulfamoyl; alkylsulfamoyl; vinylsulfonyl; acrylamido; benzoylsulfonicimido; alkylsulfonamido; phenylsulfonamido; alkoxycarbonylamino; alkylcarbamoyloxy; alkoxyca rbonyl; alkoxycarbonyloxy; alkenylcarbonylamino; groups of the formula
wherein Y is -NH-,
alkyl, --OO-, -S-, or -CH2O; -S-fl10 wherein R'O is alkyl, phenyl, phenyl substituted with halogen, alkyl, alkoy, alka noylami no, cyano, or alkoxyca rbonyl, pyridyl, pyrimidi nyl, benzoxazolyl, benzimidazolyl, benzothioazolyl, or
--OXR9; --NHH--X-RS; --XX-R9; --CONR''R''; --SO,NR''R''; wherein R9 and X are as defined above and each Rlt is selected from H, alkyl, and alkyl substituted with 1-3 of halogen, hydroxy, phenoxy, alkoxy, aryl, cyano, cycloalkyl, alkylsulfonyl, alkylthio, alkanoyl, and alkanoyloxy; alkoxy substituted with hydroxy, cyano, alkanoyloxy, or alkoxy; phenoxy substituted with one or more of alkyl, alkoxy or halogen; or R3 and R4 combined form pentamethylene, ethyleneoxyethylene or ethylenesulfonylethylene which, with the nitrogen atom to which it is attached, forms a ring; and R5, R6, Pr7 and R8 are each selected from hydrogen and alkyl. All of the above alkyl, alkylene, alkenyl, and alkoxy moieties or substituents within the definitions of R' through R1' contain up to six carbons.
The couplers are prepared by procedures well known in the art as shown in the patent literature, e.g., U.S. Patents 2,805,218; 2,827,450; and 2,839,523. The dyes of the present invention are readily prepared, for example, by reacting the known azo dyes derived from 2-amino-3-nitro-5-acetyl thiophene and the aforesaid couplers, with benzaldehyde or a substituted benzaldehyde in acetic acid in the presence of concentrated sulphuric acid.
The invention will be further understood from the following examples which are included merely for purposes of iliustration and are not intended to limit the scope of the invention.
EXAMPLE 1
A mixture of dye 11 (2 g), benzaldehyde (1.5 g), acetic acid (25 ml) and conc. sulphuric acid (5 ml) was stirred at 1 000C. for 1.5 hours. The reaction mixture was poured into dilute ammonium acetate solution, and the product dye (III) filtered off, washed with water and dried. The yield of dye (III) was 2.5 g. Dye (11) had previously been prepared by diazotizing the known 2-amino-3-nitro-5-acetyl thiophene and coupling with N,N-diethyl m-toluidine in known manner. The product dye (liy) obtained from Example 1 when applied to polyester or its blends by known techniques such as given below, gives bright blue shades with good dyeing and fastness properties.
By using the above procedure, the foilowing dyes were obtained: Ex. Benzaldehyde Shade on No. Coupler Derivative Polyester 2 N,N-Diethyl-m-toluidine 4-Chlorobenzaldehyde Blue 3 N,N-Diethylaniline Benzaldehyde Blue 4 N,N-Diethyl-m- toluidine 4-Methylbenzaldehyde Blue 5 N,-Ethyl-o-toluidine Benzaldehyde Reddish-blue 6 2,5-Dimethyl-N-ethyl Benzaldehyde Reddish-blue aniline 7 N-Ethyl-N-hydroxyethyl Benzaldehyde Blue aniline 8 N,N-Diethyl-m- toluidine 4-Carbomethyoxy- Blue Benzaldehyde 9 N-Ethyl-2 ,7-dimethyl Benzaldehyde Greenish-Blue tetrahydroquinoline 10 N,N-Diethyl-2,5 Benzaldehyde Greenish-blue dimethoxyaniline 11 N-Ethyl-3,6-dimethyl- Benzaldehyde Greenish-blue 1 ,4-benzoxazine 1 2 N.N-Diethyl-m- toluidine 4-Hydroxybenzaldehyde Blue The dyeing of the fibre material may be carried out for example from an aqueous suspension in the presence of carriers at between about 800 and 1 000C. in the absence of carriers between about 100-1 300C., or using the so-called thermofixing process at about 1 80- 2300 C. Printing of the material can be carried out by steaming the goods, printed with the new dyestuffs, in the presence of a carrier at terrperatures between 800 and 11 00 C. or in the absence of a carrier at 110-1 400C., or also by treating the printed material according to the thermofixing process at 1 80-2300C.
A typical general procedure by which polyester, e.g., poly(ethylene terephthalate) can be dyed with the present dyes is as follows: The dye cake is dispersed by heating and agitating a dyepot containing the dye cake and methyl cellosolve. When the dyecake has been ground free of lumps and dissolved as much as possible in the methyl cellosolve, 2% based on weight of the fabric of Igepon T-5 1 and 2.0% based on weight of the fabric of sodium lignin sulfonate from a premixed solution of the two components is added. Sufficient demineralized water is added to make about a 30:1 bath ratio of water to dye and a small amount of Versene 100 (sodium salt of ethylenediaminetetracetic acid) and Tanalon JDM-72 (dye carrier) are added. The pH of the dyebath is adjusted to about 5.0 with acetic acid.The fabric samples (wet-out) are entered into the dyepot and the entire contents thereof entered into a pressure dyeing container. The container is sealed and entered into a High Temperature Launder Ometer which is heated to 4S0C. and rotation thereof started. The temperature of the Launder-Ometer is raised to 1290C. at the rate of about 2.80C. per minute, and maintained at this temperature for 1 hour. The Launder-Ometer is then cooled, and the fabric samples removed and scoured in demineralized water containing 1 g/l of neutral soap and 1 g/i sodium carbonate. The samples are rinsed in cold demineralized water and dried at 1 21 OC. in a forced air oven.
The following tables show exemplary dyes of the present invention.
TABLE 1
R Rl R2 R3 R4 H H H -CH2CH3 -CH2CH2OCOCH2 Ir It CH2 CN " " " CH2CH20COCH3 -CH2CH20COCH2 .. .. " CH2CH2CN -CH 2CH2OH " CH2CH20COCH3 . . " CH2CH2CN ,, ,, 1, -CH2CH20H -CH2CHN CH2CH2NX -CH2CH2CN -CH2CH20C0Q H, 4-CI I, ,, II -CH2CH2CH2CH2 4CH a " " -CH2CH3 -CH2C6H5 H ,, ,, -C, H,1 -CH2CHCH20H OH " " CH2CH20H TABLE 1(Continued)
R Rl R2 R3 R4 H H H -C8 H,, -CH2CH a -CH2CH2 0 II -CH2CH20CH2 -CH2CH2COCH2 -CH3 ,, -CH2CH20H -CH2CH20H ,, ,, ,, -CH,CH, " " CH2CH20COCH3 -CH2CH20COCH, .. " " CH2CH3 -CH2CHCH2OH OH 4-OCOCH3 " " Ir -CH2CH2CN H ,I -CH2CH2Cl -CH2CH2S02CH2CH2 -NHCOCH3 -CH2CH2 -CH2CH1 4-OH , ,, I, -CH2CH2CN 4-CI ,, ,, -CH2CH20C0CH2 -CH2CH20C0CH2 2-CI - CH3 -CH3 -H -CH2CH2CN 4-N 2 .. ,, -CH(CH3)CH2CH3 H H -OCH2 H { TABLE 1 (Continued)
R R' R2 R3 R4 2-CH3 CH3 H -CH2CH2 -CH2CH2SO2NH2 4NO2 -NHCOCH, " H -CH24 2-CI ,I -CH2CH20CH3 2-OCH3 " ,, ,, -CHCH a CH2CO2CH2CH 4-OCH3 " ,, -CH-CH2CH(CH3)2 CH2CH(CH3)2 3NQ ,, ,, -CH2CH(CH2)4CH2OH OH 2-OH " ,, .. -CH(CH3)-CH2CH3 H H CH3 CI) H ,, CH2CH2CN 2-CH3 .. .. CH2 CH3 0 II 4-CH3-C ,, CH2CH3 CH2CH3 4-CH3 " ,, .. CH2C6H5 2-OCH3 ,, ,, " C8 H11 TABLE 1 (Continued)
R Rl R2 R3 R4 3-OCH3 H H CH2CH3 CH2CH2OH 4-OCH3 ss CH2CH2OCOCH3 0 4-COCH2 " " " CH2CH(OH) CH2OH 2-CI ,, I, ,, CH2CH2CN 4-CI ,, I, CH2CH2CN 44uCH2)2 s f,, ,, CH2CH2OH 2-OH ,, ,, CH2CH2OCOCH3 3-CN II ,, ,1 CH2CH2OCOC6H5 4-CN ' ,, CH2CH2OH CH2CH2OH H " .. CH2CH2OCOCH3 CH2CH2OCOCH3 2-CH2 ,, .. -CH2CH2S02CH2CH2 2-OCH3 Cl Cl H CH2CH2CN 0 II H CH3 H CH2CH3 CH2CH-CH20CCH2 OCCH3 0 CH2CH3 TABLE 1(Continued)
R R' RZ R3 R4 0 4-CH2-C- CH3 H CH2CH3 CH2CH2OH H " " . . CH2CH2 NH2 3-OCH3 ,I ,, 3NO2 " " CH2CH2CN H NHCOCH3 " CH2CH3 CH2CH3 ., " " " CH2CH20COCH3 (CH2CH2O)2CH2CH3 4QH,)2 H5)2 NHCOC6 H,, ,, CH2CH2CONH2 H .. CH3 H CH2CH3 " NHCOCH3 SOCH, CH2CH3 2-CH2 " " ,, " CH2CH2OCOCH3 4-CH3 " ,, ,, CH2CH(OH)CH3 2-OCH3 ,, ,, CH2CH2OH CH2CH2OH 2-OH ,, CH2CH2OCOCH3 CH2CH2OCOCH3 4-co2CH3 ,. ,, CH2CH2 2-CI NHCOCH3 H CH2CH3 cH2cH2Oc%H 4-CI C H2CH2S TABLE II
Pr Pr1, Per2, Pr3, R6, Pr7, R3 Pr2 H 2,7di-CH2 -C2H40H H 2,5-di-CH34-OCH3 CH2CH(OH)CH2OH H 2,2,4,7-tetra-CH2 -C2 H4 CONH2 H 2,2,4-tri-CH2 -C2 H4 NHCOCH3 H 2-CH3-7NHCOCH3 -C2 H4 CN 2-CH, 2,2,4-tri-CH3-7NHCOCH3 -C2 H4 Cl 4-OCH3 2CH(CH,),-7NHCOCH, -C2 H4 OCOCH, H 7H2 -C2 H4 OC2 H,, H 3-CN-7 -C, H, CONHC, H, H 3-CONH,-7-CH, -C2 H4 CONHC2H H 3-Ci-7-CH, -C2 H4 CONHCH2 C6 H, H 3CH2qH2 -C, H, 0OCOC2H,, 2-CI 2, 2, 4-d i -CH3-5, 8 -d i -OCH -C2 H4 NHCOCH=CH2 4-CI 2,2,4-tri-CH3-8-OCH3 -CH,C,HS 4-CO2C2H5 C, H5 2-CH3-7NHCOCH3 -C2 H4 CONHCH2OH 4-CH2 CO 3-OH-7-CH3 -C2 H6 NHCONH C2 H, 4-Br 2,7-di -CH3 -C2 H, 2-CN 2, 5-di-CH,-8-OCH, -C2 H4 SO2 NH2 4-OCH 2,24,7-tetra-CH,, -C2 H4 SO2 NH C2 H 5 4-OH 2,2,4tri-CH, -C2 H4 SUCH, -CHH25-7%5 20H 2-CH24HC0CH,, 2NO, 2, 2, 4-tri -CH 3-7 NHCOCH 3 -CH2CH2-S4HH H 2,2,4-tri-CH3-7NHCOC2Hs C2H,, TABLE II (Continued)
R Pr', R2, R5 R6 Rv R3 R3 C , OCH2 H 2-CH(CH,),-7NHCOCH, -CH2CH2N tOCH-! H 7 -CH w2H4C xCONC H3 4N02 3-CN-7-CH3 OcH2 H 3-CONH2-7-CH3 -CH2CHCH20H OH "-9 44u(CH2)2 3-Cl-7-CH2 -C2H4N \COCH2 COH2 4NiC2H5)2 3-OCH3-7-CH3 -C2H4-N "Co-c H2 vCOCH2 4-CH3 CO 2,2,4-di-CH3-5,8-di-OCH3 -c2H4-N H2 \COCH2 Cc /\ /CH4 2NO2 2,2,4-tri-CH3-8-OCH3 -c2H4-Nv /c6H4 'co CO-NH 4-CI 2-CH3-7NHCOCH3 -C2H4-N\ CO-CH2 COCH 4-CH2 3-OH-7-CH3 -c2H4-N\ t COCH2 9 /c 2-CH2 2,7 -d i -CH, C2HN\5Q TABLE II (Continued)
Pr Per', R2, Rs R6 R7 R3 R3 CO -s 3-CH2 2,5-di-CH3-8-OCH3 -C2H4-N INjYC2H5 \Co-CH, $I CLHg 4-OCH, 2, 2,4,7-tetra-CH, -C2H4-SS,,CH scHC2lHs 4CH2 2,2,4,7-tetra-CH3 -C2H4- NeCH COH2 -C2H4-N 4-CN 2,2, 4-tri -CH3 %H2H2 9 H 2-CH3-7NHCOCH3 -C2H4NHC 9 H 2,2,4-tri-CH ,-7NHCOCH, -C2H4NHC H 2-CH(CH3)2-7NHCOCH3 --CH2CH255 NFH H 7-CH1 CH2CH2-%$%2 H 3-CN-7-CH3 -C2 H4 OH 9 A H 3-CONH2-7-CH3 -CH2CHN,,52 H 2,2,4,7-tetra-CH2 cH2CH2OCNH H 2,2,4,7-tetra-CH2 cH2CH2N TABLE III
R Rt, R2, R5 R3 H 3,6-di-CH3 -C2 H4 OH H 3-CH3 CH2CH(OH) CH2OH H 3-CH,-6-NHCOCH, -C,H4 CONH2 H 6NHCOCH3 -C2H4 NHCOCH3 H 3, Sdi-CH3 -C2 H4 CN H 3-CH3 -C2H4 Cl H 3-CH3-6-NHCOCH3 -C2 H4 OOCC2 H3 H H 6NHCOCH3 -C2 H4 OC2 H, H 3,6Zi-CH3 -C2H4 CONHC2H1 H 3-CH2 -C2 H4 CONHC2 Hs H 3-CH3-6-NHCOCH3 -C2H4C0NHCH2C6H,, H 6-NHCOCH3 -C2 H4 OCOC2 Hs H 3,64i-CH3 -C2H4 NHCOCH=CH2 H 3-CH -CH2C6H,, H 3-CH3-6-NHCOCH3 -C2 H4 CONHCH2OH H 6NHCOCH3 -C2 H6 NHCONHC2 H, H 3,6-di-CH, -C2 H5 H 3-CH3 -C2 H4 SO2 NH2 H 3-CH2-NHC0CH2 -C2 H4 SO2 NHC2H,, H 6NHCOCH3 -C2 H4 SUCH, H 3,6-di-CH, -CH2CH2S H 3,6di-CH2 N 2-CH3 3-CH2 TABLE III (Continued)
R Per', R2, R5 R3 C OCH2 4-CH2 3-CH3-6NHCOCH3 -CH2CH2N 'COCH2 2-OCH3 6NHCOCH3 F"Y""3 4-OCH3 3,6-di-CH3 -C2H4-S \COCH2 2NO2 3-CH -CH2CHCH2OH OH 4NO2 3-CH3-6NHCOCH3 -C2H4-N & CO \COCH2 COCH2 2-CI 6NHCOCH3 -C2H4-N "Cc-CH2 FOC2 2-OH 3,6-di-CH3 -C2N#OCH;;H2 %OCH2 CO 4miCH3 )2 3-CH2 co CO /CO - NH 4NiC2Hs)2 3CH,-GNHCOCH, I CO-CH2 COCH > RL 4-CH3 CO 6NHCOCH3 /cocH3 C2HN\ / COCH2 o 4-C-OCH3 3,6-di-CH3 -c2H4-N/ TABLE III (Continued)
R Rl, R2, R5 R3 O 'cO-s II 3-C, -C2H4-N 4-COC2H,, 3-CH3 \coCH2 S1-iC2H5 2-CN 3-CH3-6NHCOCH3 -C2H4-SC NAH COCH2 4-CN 6NHCOCH3 -C2H4-N I SH2CH2 2-OCH, 3,6-di-CH, -c2H4NHct 4-OCH3 3-CH2 -C 2H4NHOCH3 H 3-CH3-6-NHCOCH3 -CH2CH2SC SH o H 6NHCOCH3 -CH2CH2-/ H 3,6-di-CH3 -C2 H4 OH 8 H 3-CH2 CH2CH2-){%i H 3, di-CH2 C'2CH2CCNH 8 /a/9 H 3,6di-CH,

Claims (13)

1. A compound having the formula
in which R is hydrogen or 1-3 groups selected from alkyl, hydroxy, alkoxy, halogen, nitro, alkoxyca rbonyl, alkanoyl carbonyl, alkanoyl, alkylamino, carboy, cyano, dialkylamino, and alkyl substituted with 1-3 of halogen, alkoxy, alkanoyl, alkanoyloxy, alkoxycarbonyl, alkanoylamino, cyano, nitro, carbamoyl, alkylcarbamoyl, sulfamoyl, or alkylsulfamoyl; and C' is an aniline, tetrahydroquinoline, or benzomorpholine type azo type dye coupler.
2. A compound of Claim 1 wherein the coupler has one of the formulae
wherein R' and R2 are each selected from hydrogen, fluorine, chlorine, bromine, alkyl, cycloalkyl, alkoxy, phenoxy, alkylthio, arylthio, and radicals having the formula -NH-X-Pr9 in which X is -CO-, -COO-, or-SO2- and R9 is selected from alkyl and alkyl substituted with halogen, hydroxy, phenoxy, aryl, cyano, cycloalkyl, alkylsulfonyl, alkylthio, alkanoyloxy, and alkoxy, and when X is -CO-, R9 also can be hydrogen, amino, alkenyl, alkylamino, dialkylamino, arylamino, aryl, orfuryl; R3 and R4 are selected from hydrogen; cycloalkyl; cycloalkyl substituted with one or two groups selected from alkyl; -OH, alkoxy, halogen and hydroxy substituted alkyl;phenyl or phenyl substituted with alkyl, alkoxy, halogen, alkanoylamino, cyano or alkoxycarbonyl; straight or branched alkenyl; straight or branched alkyl and such alkyl substituted with 1-3 of the following: hydroxy, halogen; cyano; amino; alkoxy; hydroxyalkoxy; succinimido; glutarimido; phenyicarbamoyloxy; phthalimido; phthalimidino; 2-pyrrolidoXno; cyclohexyl; phenoxy; phenyl or phenyl substituted with alkyl, alkoxy, halogen, alkanoylamino, cyano or alkoxycarbonyl; alkanoylamino; sulfamoyl; alkylsulfamoyl; vinyisulfonyl; acrylamido; benzoylsulfonicimido; alkylsulfonamido; phenylsulfonamido; alkoxycarbonylamino; alkylca rbamoyloxy; alkoxycarbonyl; alkoxycarbonyloxy; alkenylcarbonylamino; groups of the formula
wherein Y is -NH-,
alkyl, -0--S-, --S--, or --CH2O; --S--R10 wherein R'O is alkyl, phenyl, phenyl substituted with halogen, alkyl, alkoy, alkanoylamino, cyano, or alkoxyca rbonyl, pyridyl, pyrimidinyl, benzoxazolyl, benzimidazolyl, benzothioazolyl, or
--OXR9; --NHH--X-RS; --XX-R9; --CONR''R"; --SO,NR''R''; wherein R9 and X are as defined above and each R" is selected from H, alkyl, and alkyl substituted with 1-3 of halogen, hydroxy, phenoxy, alkoxy, aryl, cyano, cycloalkyl, alkylsulfonyl, alkylthio, alkanoyl, and alkanoyloxy; alkoxy substituted with hydroxy, cyano, alkanoyloxy, or alkoxy; phenoxy substituted with one or more of alkyl, alkoxy or halogen; or R3 and R4 combined form pentamethylene, ethyleneoxyethylene or ethylenesulfonylethylene which, with the nitrogen atom to which it is attached, forms a ring; and R5, R6, Pr? and R8 are each selected from hydrogen and alkyl.
3. A compound of Claim 1 wherein the coupler has one of the formulas
wherein R' is alkyl, alkoxy, alkanoylamino, or alkoxycarbonyiamino; R2 is hydrogen, alkyl or alkoxy: R3 and R4 are the same or different and selected from hydrogen, alkyl and alkyl substituted with hydroxy, alkoxy, alkoxyalkoxy, hydroxyalkoxy, carbamoyl, alkylcarbamoyl, alkanoylamino, sulfamoyl, alkylsulfamoyl, phenyl, cyclohexyl, 2-pyrrolidono, phthalimidino, succinimido, cyano, phenoxy, alkylsulfonyl, phthalimido, benzoylsulfonicimido, triazolylthio, alkylsulfonamido, -SO2NHPr11, phenylsulfonamido, alkoxycarbonylami no, alkylca rbamoyloxy, alkoxyca rbonyl, alkoxycarbonyloxy,
R5 and R7 are each hydrogen or alkyl.
4. The compound of Claim 1 having the formula
5. The compound of Claim 1 having the formula
6. The compound of Claim 1 having the formula
7. The compound of Claim 1 having the formula
8. The compound of Claim 1 having the formula
9. The compound of Claim 1 having the formula
10. The compound of Claim 1 having the formula
11. Compounds as claimed in Claim 1 and substantially as hereinbefore described, other than the compounds specifically claimed in Claims 4 to 1 0.
12. The method of dyeing textile fibers with a dye as claimed in Claim 1.
13. Textile fibers dyed by the method of Claim 12.
GB08200914A 1982-01-13 1982-01-13 Azo dyes Expired GB2113702B (en)

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Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB2147599A (en) * 1983-10-07 1985-05-15 Kodak Ltd 2-amino-cinnamoylthiophene disperse azo dye compounds

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB2147599A (en) * 1983-10-07 1985-05-15 Kodak Ltd 2-amino-cinnamoylthiophene disperse azo dye compounds

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