GB2036777A - Disperse monoazo dyes - Google Patents
Disperse monoazo dyes Download PDFInfo
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- GB2036777A GB2036777A GB7935947A GB7935947A GB2036777A GB 2036777 A GB2036777 A GB 2036777A GB 7935947 A GB7935947 A GB 7935947A GB 7935947 A GB7935947 A GB 7935947A GB 2036777 A GB2036777 A GB 2036777A
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- alkylsulphonyl
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- 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
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/04—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to the ring carbon atoms
- C07D215/06—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to the ring carbon atoms having only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, attached to the ring nitrogen atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen 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
- C07D215/38—Nitrogen atoms
-
- 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
- C09B43/00—Preparation of azo dyes from other azo compounds
- C09B43/40—Preparation of azo dyes from other azo compounds by substituting hetero atoms by radicals containing other hetero atoms
- C09B43/42—Preparation of azo dyes from other azo compounds by substituting hetero atoms by radicals containing other hetero atoms by substituting radicals containing hetero atoms for —CN radicals
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- Organic Chemistry (AREA)
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- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Azo dyes having a substituted phenyl azo moiety and an acylaminotetrahydroquinoline coupler moiety containing either substituents are particularly useful for dyeing polyester textile materials in yellow to turquoise shades. The dyes have the general formula <IMAGE> wherein X is selected from chlorine, bromine, fluorine, cyano, nitro, trifluoromethyl, lower alkoxy, lower alkoxyalkoxyalkanoyloxy, lower alkylsulphonyl, arylsulphonyl, chloroarylsulphonyl, lower alkylsulphonyl substituted with halogen, lower alkoxycarbonyl, aroyl, aroylsulphonyl, and lower alkanoyl radicals; n is 1-3; A is an acyl radical; R, R<1> and R<3> are the same or different and each is hydrogen or lower alkyl; R<2> is hydrogen, lower alkyl, lower alkoxy, or lower alkanoyloxy; R<4> is hydrogen, lower alkyl, or lower alkoxy; and R<5> is lower alkyl or cyclohexyl.
Description
SPECIFICATION
Disperse monoazo dyes
This invention relates to azo dye compounds, and particularly to azo dye compounds having a substituted phenyl azo moiety and an acylamidotetrahydroquinoline coupler moiety containing ether substituents, and to polyester textile materials dyed therewith.
The azo dyes of this invention produce yellow to turquoise shades on polyester textile materials such as poly(ethylene terephthalate). These dyes possess excellent brightness, dyeability, build-up and fastness properties including sublimation, on polyester fibres as tested according to standard procedures described in the Technical Manual of the American Association of Textile Chemists and
Colorists. For example, the dyes of this invention exhibit superior fastness properties and superior brightness on polyester fibres when compared with the azo compounds disclosed in United States
Patent Specification No. 2,249,774. Also, the dyes of this invention show considerable advantage over the dyes of United States Patent Specification No. 3,635,941 in that the dyes of this invention can be applied at lower temperatures, making them especially useful for the exhaust dyeing of polyesters.In addition, they penetrate the fibres more readily and completely to provide level uniform dyeings even at temperatures below that required for complete exhaustion of the dvebath.
The dyes of this invention have the general formula
wherein
X is selected from chlorine, bromine, fluorine, cyano, nitro, trifluoromethyl, lower alkoxy,
lower alkoxyalkoxyalkanoyloxy, lower alkylsulphonyl, arylsulphonyl, chloroarylsulphonyl, lower
alkylsulphonyl, substituted with halogen, lower alkoxycarbonyl, aroyl, aryloxysulphonyl, and lower
alkanoyl radicals; n is 1-3; A is an acyl radical;
R, R1 and R3 are the same or different and each is hydrogen or lower alkyl;
R2 is hydrogen, lower alkyl, lower alkoxy, or lower alkanoyloxy;
R4 is hydrogen, lower alkyl, or lower alkoxy; and
R5 is lower alkyl or cyclohexyl.
The acyl radical A can be formyl, lower alkanoyl, aroyl, cyclohexylcarbonyl, lower alkoxycarbonyl, aryloxycarbonyl, lower alkylsulphonyl, lower alkoxysulphonyl, cyclohexylsulphonyl, arylsulphonyl, aryloxysulphonyl, carbamoyl, lower alkylcarba moyl, aryicarbamoyl, sulphamoyl, lower alkylsulphamoyi and furoyl. The lower alkanoyl radical can be substituted with halogen, aryl, cyano, lower alkoxy, benzyloxy, lower alkylthio, lower alkylsulphonyl and lower alkoxysulphonyl groups. The alkylsulphonyl and alkoxysulphonyl radicals can be substituted with cyano, hydroxy and halogen. The alkoxycarbonyl radical can be substituted with hydroxy, lower alkoxy, lower alkoxyalkoxy, and cyano.Acetyl, propionyl, butyryl, cyanoacetyl, chloroacetyl, trifluoroacetyl, phenyiacetyl, methoxyacetyl, methylthioacetyl, methylsulphonylacetyl, methoxycarbonyl, propoxycarbonyl, butoxycarbonyl, methylsulphonyl, ethylsulphonyl, propylsulphonyl, butylsulphonyl, 2-cyanoethylsulphonyl, 2-hydroxyethylsulphonyl, 2chloroethylsulphonyl, methoxysulphonyl and ethoxysulphonyl are examples of the alkanoyl, alkoxycarbonyl, alkylsulphonyl, and alkoxysulphonyl radicals that A represents. The aryl portion of the arylalkanoyl, aroyl, aryloxycarbonyl, arylsulphonyl, aryloxysulphonyl, and arylcarbamoyl groups is monocyclic, such as unsubstituted phenyl and phenyl substituted with, for example, 1 to 3 groups selected from lower alkyl, lower alkoxy and halogen.Tolyl, anisyl, p-bromophenyl, and o,p-dichlorophenyl iilustrate the aryl portion. Dimethylcarbamoyl, ethylcarbamoyl, propylcarbamoyl, butylcarbamoyl, and dimethylsulphamoyl illustrate the alkylcarbamoyl and alkylsulphamoyl radicals that A represents. Methyl, ethyl, propyl, isopropyl, isobutyl and butyl are lower alkyl radicals and methoxy, ethoxy, propoxy, and butoxy are lower alkoxy radicals. Examples of the alkanoyloxy radicals are acetoxy, propionoxy, butyroxy and isobutyroxy. The term "lower" means a carbon content of 1-6 carbon atoms.
Preferred dyes of this invention are those having the formula
wherein
Y is chlorine, bromine or cyano;
Z is nitro or cyano;
A is lower alkanoyl, benzoyl, lower alkoxycarbonyl, lower alkysulphonyl or lower
alkylcarbamoyl;
R is methyl or, when R1 or R3 is hydrogen, R is lower alkyl;
R' and R3 are each hydrogen or methyl;
R2 and R4 are hydrogen; and R5 is lower alkyl.
The following examples A-C describe procedures for preparing couplers that can be used to make the dyes of this invention.
EXAMPLEA 2,2,4-Trimethyl-1 ,2,3,4-tetrahydroquinoline (87.5 g), 2-(2-ethoxyethoxy)ethyl chloride (127 g), anhydrous sodium carbonate (58 g), and sodium iodide (7.5 g) were heated at 190--2000C. for 5 hours. The salts were extracted with water, and the organic layer was distilled. The product, 1 -[2-(2- ethoxyethoxy)ethyl]-2,2,4-trimethyl-1 ,2,3,4-tetrahyd roquinoline, was removed at 139-154 C. at 0.3-0.4 mm pressure. A 58 g portion of the product was added slowly to 1 50 ml of 100% H2SO4 at about 100C.A solution of 13.5 g of 98% HNO3 and 17 ml of 100% K2SO4wasadded at0-50C. After an additional hour, the material was drowned in an ice-water mixture, neutralized with 50% sodium hydroxide solution, and extracted with 300 ml of isopropanol. The solution of the 7-nitro compound was hydrogenated in the presence of palladium on carbon at 750C. at a hydrogen pressure of 3450 kilopascals. After removal of the catalyst, the solution of the 7-amino compound was treated at 5--1 OOC. with acetic anhydride (20 ml), added during 15 minutes. After a further 15 minutes, the excess acetic anhydride was hydrolyzed with water and the solution was evaporated to dryness.The product 7-acetamido-1 -[2-(ethoxyethoxy)-ethyl]-2,2 4-trimethyl- 1 ,2 ,3,4-tetrahydroquinoline, was dissolved in sufficient acetic acid to form 400 g of coupler solution.
EXAMPLE B
7-Acetamido-2,2,4-trimethyl-1,2,3,4,-tetrahydroquinoline (6.97 g), 2-(2-ethoxyethoxy)ethyl chloride (7.63 g), anhydrous sodium carbonate (3.18 g), and sodium iodide (0.45 g) wer heated at 150-1 600C. for 9-10 hours. The mixture was slurried with 20 ml of water, then neutralized with 10% HCI solution and poured into 500 ml of 2% HCI solution, using 1 5 ml of acetone to rinse the flask.
The solution was extracted with hexane to remove the excess 2-(2-ethoxyethoxy)ethyl chloride. The
aqueous layer was neutralized with ammonium hydroxide to recover the product, 7-acetamido-l -[2-(2- ethoxyethoxy)ethyl]-2,2,4-trimethyl- 1 ,2,3,4-tetrahydroqu inoline, as a semisolid. It was slurried in water, which was poured off, and dried to constant weight.
EXAMPLE C
When the procedure described in Example B was followed with an equivalent quantity of 2-(2isobutoxyethoxy)ethyl bromide substituted for the 2-(2-ethoxyethoxy)ethyl chloride, the product was 7aceta mido-1 -[2-(2-isobutoxyethoxy)ethyl]-2,2,4-trimethyl-1,2,3,4-tetrahydroqu inoline.
Examples of other alkylating agents which can be used are as follows: 2-(2-methoxyethoxy)ethyl bromide, 2-(2-methoxyethoxy)ethyl chloride, 2-(2-ethoxyethoxy)ethyl bromide, 2-(2- isopropoxyethoxy)ethyl chloride, 2-(2-butoxyethoxy)ethyl bromide, 2-(2-butoxyethoxy)ethyl chloride, 2 (isobutoxyethoxy)ethyl chloride, 2-(2- tert-butoxyethoxy)ethyl chloride and 2-(2-pentoxyethoxy)ethyl bromide.
EXAMPLES OF DYE PREPARATION
EXAMPLE 1
2-Cyano-4,6-dinitroaniline (2.08 g) was slurried in 35 ml of 70% H2SO4 at 1 50C. The mixture was cooled to - 20C. and a solution of 0.72 g. sodium nitrite in 5 ml of concentrated H2SO4 was added at - 2 to OOC. The reaction mixture was stirred at OOC. for 3 hours and was then added to a solution of 3.48 g of 7-acetamido- 1 -[2-(2-ethoxyethoxy)ethyl]-2,2,4-trimethyl-1,2,3,4-tetrahydroquinoline dissolved in 100 ml of concentrated H2SO4 at below 1 OOC. After coupling for 1 hour, the dye was precipitated by drowning in water, collected by filtration, washed with water, and air dried.The product, 6-(2-cya no-4, 6-dinitrophenylazo)-7-acetamido- 1 -[2-(2-ethoxyethoxy)ethyl]-2,2,4-trimethyl- 1,2,3,4tetrahydroquinoline, produced a bright greenish-blue shade on polyester fibres and had excellent lightfastness and resistance to sublimation.
EXAMPLE 2
The procedure described in Example 1 was repeated except that 3.76 g of 7-acetamido-1 -[2-(2- isobutoxyethoxy)ethyl]-2 ,2 ,4-trimethyl- 1,2,3 4-tetrahydroquinoline was substituted for the coupler of
Example 1. The product obtained,6-(2-cyano-4,6-dinitrophenyiazo)-7-acetgamido-1 -[2-(2- isob utoxyethoxy)ethylj-2,2 ,Ctrimethyl-l ,2 ,3,4-tetrahydroquinoline, produced a bright blue shade on polyester fibres.
EXAMPLE 3
Sodium nitrite (4.0 g) was added portionwise to 50 ml of concentrated H2SO4, with the temperature rising to 700C. The solution was cooled, and 25 ml of 2:5 acid (2 parts propionic to 5 parts acetic acid) was added below 1 00C. The solution was cooled to O--SoC..~and 2-bromo-4,6dinitronaniline (13.1 g) was added, followed by25 ml additional 2:5 acid and lOgof ice. After being stirred at 0--1 OOC. for 3-4 hours, the diazonium solution was added in portions to the coupler solution.The coupler solution was made by adding 160 ml of cold water to 120 g of a solution of 1 7.43 g of 7-aceta mido-l -[2-(2-ethoxyethoxy)ethyl]-2 ,2,4-trimethyl-l ,2,3,4-tetrahydroquinoline in acetic acid, followed by 10 g of concentrated H2SO4 and sufficient ice (130 g) to lower the temperature to OOC. The temperature was maintained at 0-50C. during coupling by means of an ice bath. After stirring for 1/2 hour at 0-50C., 50% NaOH solution was added, along with sufficient ice to prevent the temperature from exceeding 1 OOC. When the material became only weakly acidic, it was drowned into water. The product was collected by filtration, washed with water, and dried in air.The azo compound obtained, 6-(2-bromo-4,6-dinitrophenylazo)-7-acetamido-1-[2-(2-ethoxyethoxy)ethyl]-2,2,4-trimethyl 1 ,2,3,4-tetrahydroquinoline, produced reddish-blue shades having good fastness to light and excellent sublimation resistance on polyester fibres.
EXAMPLE 4
The procedure described in Example 3 was repeated except that 100 g of acetic acid solution containing 18.83 g of 7-acetamido-1-[2-(2-isobutoxyethoxy)ethyl]-2,2,4-trimethyl-1,2,3,4- tetrahydroquinoline was substituted for the coupler of Example 3. The product obtained was bromo-4,6-dinitrophenylazo)-7-acetamido-1 -[2-(2-isobutoxyethoxy)ethyl]-2 ,2,4-trimethyl-1 2,3,4- tetrahydroquinoline, a reddish-blue dye of good fastness to light and excellent sublimation fastness on polyester fibres. The analogous 7-propionamido dye also imparts reddish-blue shades to polyester fibres.
EXAMPLE 5 6-(2-Bromo-4,6-dinitrophenylazo)-7-acetamido- 1 -[2-(2-ethoxyethoxy)ethyl]-2,2,4-trimethyl- 1 ,2,3,4-tetrahydroquinoline (1.00 g) and cuprous cyanide (0.22 g) were added to pyridine (20 ml) and heated at 11 2-11 40C. for one hour, then drown-ed in water. The solid was collected by filtration, dissolved in hot 2-m.ethoxyethanol, and filtered. The filtrate was treated with hot water until crystallization began. The product was removed by filtration of the material at room temperature. The product, 6-(2-cyano-4,6-dinitrophenylazo-7-acetamido-1-[2-(2-ethoxyethoxy)ethyl]-2,2,4-trimethyl 1 ,2,3,4-tetrahydroquinoline, was identical to the product of Example 1.
EXAMPLE 6
N,N-Dimethylformamide (14 ml) and 2.48 g of cuprous cyanide were added to a solution of 1.35 g of cuprous cyanide in 10 ml of water. The material was heated at 45--500C. until all the cuprous cyanide had dissolved, then was added to a solution of 31.08 g of 6-(2-bromo-4,6-dinitrophenylazo)-7acetamido-1-[2-(2-ethoxyethoxy)ethyl]-2,2,4-trimethyl-1,2,3,4-tetrahydroquinoline in 158 ml of N,Ndimethylformamide at 90-95 C. After one hour, the material was diluted with 312 ml of isopropanol.
The dye was removed by filtration at OOC. washed with 50 ml of isopropanol, and then with water. The dye was identical to the dye of Examples 1 and 5.
The dyes described in the following table are prepared according to the procedures described in the preceding examples and conform to the above general formula.
Example
No. X A * R, R, R, R R4 R5
7 2-CN-4,6-di-NO2 CH3CO- 2,2,4-tri-CH3 -CH3
8 '' '' '' -CH2CH2CH3
9 '' '' '' -CH(CH3)2
10 '' '' '' -(CH2)3CH3
11 '' '' '' -CH2C(CH3)3
12 '' '' '' -(CH2)5CH3
13 '' C2H5CO- '' -CH3
14 '' '' '' -CH2CH3
15 '' '' '' -CH2CH(CH3)2
16 '' C6H5CO0 '' -CH2CH3
17 '' C2H5OC2H4CO- '' ''
18 '' C2H5OC2H4OCO- 2-CH3 ''
19 '' CH3CO- 2,4-di-CH3 ''
20 '' C2H5CO- '' ''
21 '' (CH3)2CHO- '' -CH3
22 '' CH3CO 2-CH3 -CH2CH3
23 '' '' 2-CH(CH3)2 ''
24 '' '' 3-OCH3 ''
25 '' '' 2,2,4-tri-CH3-8-OCH3 '' Example
No.X A * R, R, R, R R4 R5
26 2-Br-4,6-di-NO2 HCO- 2,2,4-tri-CH3 -(CH2)3CH3
27 '' CH3CO- 2-CH3 -(CH2)3CH2
28 '' C2H5OCO- **None -CH2CH(CH3)2
29 '' CICH2CO- '' ''
30 '' CH3OCH2CH2CO- 2,2,4-tri-CH3 -CH3
31 '' C6H5CH2CO- '' ''
32 '' C6H5OCH2CO- '' ''
33 '' C2H5OCOCH2CH2CO- '' ''
34 '' CH3COOCH2CH2CO- '' ''
35 2-Cl-4,6-di-NO2 CH3CO- '' ''
36 '' '' 2-CH3 -C6H11
37 2,6-di-Br-4-NO2 '' 2,2,4-tri-CH3 -CH2CH3
38 '' C2H5CO- 2,2,4,5-tetra-CH3 -CH(CH3)2
39 2,6-di-CN-4-NO2 '' ** None ''
40 '' CH3CO- 2,2,4-tri-CH3 -CH2CH3
41 '' C2H5CO- 2-CH3 ''
42 '' CH3SO2- 2-CH(CH3)2 -(CH2)3CH3
43 2,6-di-Cl-4-NO2 CH3CO- 2,2,4-tri-CH3 -CH2CH3
44 2-Br-4-NO2-6-SO2CH3 '' '' '' Example
No. X A * R, R, R, R R4 R5
45 2-CN-4-NO2-6-SO2-C6H4-p-Cl CH3CO- 2,2,4-tri-CH3 -CH2CH3
46 2-CN-4-NO2-6-SO2OC6H5 HCO- 2-CH(CH3)2 -CH3
47 2,4-di-SO2CH3-6-CN CH3CO- 2,2,4-tri-CH3 ''
48 2-CN-4-NO2-6-CH3OCO- '' '' ''
49 2-CF3-4-NO2-6-CN '' '' ''
50 2-Br-4-NO2-6-C2H5O- '' 2-CH3 ''
C2H4OC2H4OCO- '' -C2H5
51 2,6-di-Br-4-CN '' '' ''
52 2,6-di-Br-4-CN '' 2,2,4-tri-CH3 ''
53 2,4,6-tri-CN '' '' ''
54 2,4-di-CN '' '' ''
55 2-Cl-4-CN '' 2-CH3 -CH2CH2CH3
56 2-CN-4-SO2C2H5 C2H5NHCO- 2,2,4-tri-CH3 -C2H5
57 2,4-di-NO2 p-CH3O-C6H4CO- '' ''
58 2,6-di-Br p-CH3-C6H4CO- '' ''
59 2-CN-4-NO2-6-OCH3 C6H11CO- '' ''
60 2-COCH3-4-NO2 C6H5OCO- '' ''
61 2-COC6H5-4,6-di-NO2
62 2-CN-4-NO2-6-SO2CH3 C6H11SO2- '' ''
63 2-COOC2H5-4-NO2-6-CN C6H5SO2- '' ''
Example No. X A *$R, R, R, R R4 R5 64 2,6-di-CN-4-NO2 C6H5OSO2- 2,2,4-tri-CH3 -C2H5 65 '' H2NCO- '' '' 66 '' C6H5NHCO- '' '' 67 '' H2NSO2- '' '' 68 '' C2H5NHSO2- '' '' 69 '' #-CO- '' '' 70 '' CICH2CH2CO- '' '' 71 '' NCCH2CO- '' '' 72 '' C6H5CH2OCO- '' '' 73 '' CH3SCH2CO- '' '' 74 '' CH3SO2CH2CO- '' '' 75 '' NCCH2SO2- '' '' 76 '' HOC2H4SO2- '' '' 77 '' ClC2H4SO2- '' '' 78 '' HOCH3OCO- '' '' 79 '' C2H5OC2H5OCH3OCO- '' '' 80 '' NCC2H4OCO- '' '' 81 '' CH3OSO2CH3CO- '' '' Example
No. X A *$R, R, R, R R4 R5
82 2,6-di-CN-4-NO2 NCC2H4SO2CH2CO- 2,2,4-tri-CH3 -C2H5
83 '' HOC2H4SO2CH2CO- '' ''
84 '' ClC2H4SO2CH2CO- '' '' * When any R, R, R, R and R4 is hydrogen, the hydrogen is not listed in this table.
** The word "None" indicates that R and R to R4 were all hydrogen.
The dyes of the present invention can be applied to textile materials in accordance with known disperse dyeing procedures using auxiliary dyeing agents, such as surfactants, dispersing agents, carriers and thickeners, as necessary. The dyeing can be carried out at the boil and atmospheric pressures, or at higher temperatures under pressures moderately above atmospheric pressures. The following example illustrates a carrier dyeing procedure for applying the dyes to polyester textile materials.
EXAMPLE 85
The azo compound of Example 1(01. g) was dissolved in 10 ml of 2-methoxyethanol. A small amount (3-5 ml) of a 3% by weight sodium lignosulphonate aqueous solution was added, with stirring, and the volume of the bath brought to 300 ml with water. An anionic solvent carrier (Tanavol) (3 ml) was added to the bath and 10 g of a textile fabric of poly(ethylene terephthalate) fibres was placed in the bath and worked 10 minutes without heat. The dyeing was then carried out at the boil for one hour.
The dyed fabric was removed from the dyebath and scoured for 20 minutes at 800 C. in a solution containing 1 g/litre of neutral soap and 1 g/litre of sodium carbonate. The fabric was then rinsed, dried in an oven at 121 OC, and heat set for 5 minutes at 3500 C.
The present dyes can also be applied to polyester textile materials, for example, by the heat fixation technique described in United States Patent Specification No. 2,663,612 and in the American States Patent Specification No. 2,663,612 and in the American Dyestuff Reporter, 42, (1953). This procedure can be varied by the substitution of other dispersing agents, surfactants, suspending agents, and thickeners. The temperature and time of the heat fixation step can also be varied. The polyester fabrics, yarns, fibres and filaments can also contain minor amounts of other additives such as brighteners, pigments, delustrants, inhibitors, and stabilizers. Although the azo compounds of the invention are particularly suitable for dyeing polyester textile materials, they can also be used to dye other hydrophobic textile materials such as cellulose acetate and polyamide fibres.
Claims (14)
1. A textile dye having the formula
wherein
X is selected from chlorine, bromine, fluorine, cyano, nitro, trifluoromethyl, lower alkoxy,
lower alkoxyalkoxyalkanoyloxy, lower alkylsulphonyl, arylsulphonyl, chloroarylsulphonyyl, lower
alkylsulphonyl substituted with halogen, lower alkoxycarbonyl, aroyl, aryloxysulphonyl, and lower
alkanoyl radicals; nis 1-3; A is an acyi radical;
R, R1 and R3 are the same or different and each is hydrogen or lower alkyl;
R2 is hydrogen, lower alkyl, lower alkoxy, or lower alkanoyloxy:
R4 is hydrogen, lower alkyl, or lower alkoxy; and
R5 is lower alkyl or cyclohexyl.
2. A dye as claimed in Claim 1, having the formula
wherein
Y is chlorine, bromine or cyano;
Z is nitro or cyano;
A is lower alkanoyl, benzoyl, lower alkoxycarbonyl, lower alkylsulphonyl or lower alkylcarbamoyl;
R is methyl or, when R1 or R3 is hydrogen, R is lower alkyl;
R1 and R3 are each hydrogen or methyl;
R2 and R4 are hydrogen; and R5 is lower alkyl.
3. A dye as claimed in Claim 2 having the formula
4. A dye as claimed in Claim 2, having the formula
5. A dye as claimed in Claim 2, having the formula
6. A dye as claimed in Claim 2, having the formula
7. A dye as claimed in Claim 2, having the formula
8. A dye as claimed in Claim 2, having the formula
9. A dye as claimed in Claim 2, having the formula
10. A textile dye as claimed in Claim 1 and substantially as hereinbefore described.
11. A polyester textile material dyed with a textile dye as claimed in Claim 1.
12. A polyester textile material dyed with a textile dye as claimed in Claim 2.
13. A polyester textile material dyed with a textile dye as claimed in any one of Claims 3 to 9.
14. A polyester textile material dyed with a textile dye as claimed in Claim 10.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US95142878A | 1978-10-16 | 1978-10-16 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| GB2036777A true GB2036777A (en) | 1980-07-02 |
| GB2036777B GB2036777B (en) | 1983-04-13 |
Family
ID=25491675
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB7935947A Expired GB2036777B (en) | 1978-10-16 | 1979-10-16 | Disperse monoazo dyes |
Country Status (5)
| Country | Link |
|---|---|
| JP (1) | JPS5565255A (en) |
| CH (1) | CH641195A5 (en) |
| DE (1) | DE2941512A1 (en) |
| FR (1) | FR2439221B1 (en) |
| GB (1) | GB2036777B (en) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4529406A (en) * | 1982-07-27 | 1985-07-16 | Research Association Of Dyestuff Manufacturers | Nitrothiazolyl-monoazo-2,2,4-trimethyl-1,2,3,4-tetrahydroquinoline compounds for polyester |
| US9107848B2 (en) | 2011-12-16 | 2015-08-18 | L'oreal | Coupler with cationic 7-amino-1,2,3,4-tetrahydroquinoline structure, dyeing composition comprising same, processes and uses |
| US9233060B2 (en) | 2011-12-16 | 2016-01-12 | L'oreal | Coupler with 7-amino-1,2,3,4-tetrahydroquinoline structure, dyeing composition comprising same, processes and uses |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR3072286B1 (en) | 2017-10-13 | 2022-08-12 | Oreal | PARTICULAR 7-AMINO-1,2,3,4-TETRAHYDROQUINOLEINS, METHOD AND COMPOSITION |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2249774A (en) * | 1940-07-24 | 1941-07-22 | Eastman Kodak Co | Azo compound and material colored therewith |
| US3635941A (en) * | 1969-04-01 | 1972-01-18 | Eastman Kodak Co | Disperse mono azo dyes containing an acylamidotetrahydroquinoline group |
| US3692769A (en) * | 1970-02-18 | 1972-09-19 | Max A Weaver | Azo compounds containing an arylsulfonyl phenyl diazo component |
-
1979
- 1979-10-12 DE DE19792941512 patent/DE2941512A1/en not_active Ceased
- 1979-10-15 CH CH927079A patent/CH641195A5/en not_active IP Right Cessation
- 1979-10-16 GB GB7935947A patent/GB2036777B/en not_active Expired
- 1979-10-16 JP JP13349379A patent/JPS5565255A/en active Pending
- 1979-10-16 FR FR7925645A patent/FR2439221B1/en not_active Expired
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4529406A (en) * | 1982-07-27 | 1985-07-16 | Research Association Of Dyestuff Manufacturers | Nitrothiazolyl-monoazo-2,2,4-trimethyl-1,2,3,4-tetrahydroquinoline compounds for polyester |
| US9107848B2 (en) | 2011-12-16 | 2015-08-18 | L'oreal | Coupler with cationic 7-amino-1,2,3,4-tetrahydroquinoline structure, dyeing composition comprising same, processes and uses |
| US9233060B2 (en) | 2011-12-16 | 2016-01-12 | L'oreal | Coupler with 7-amino-1,2,3,4-tetrahydroquinoline structure, dyeing composition comprising same, processes and uses |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS5565255A (en) | 1980-05-16 |
| DE2941512A1 (en) | 1980-04-24 |
| FR2439221A1 (en) | 1980-05-16 |
| FR2439221B1 (en) | 1985-10-18 |
| GB2036777B (en) | 1983-04-13 |
| CH641195A5 (en) | 1984-02-15 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 732 | Registration of transactions, instruments or events in the register (sect. 32/1977) | ||
| PCNP | Patent ceased through non-payment of renewal fee |