CA1050709A - Process for dyeing synthetic fibrous materials from organic solvents - Google Patents
Process for dyeing synthetic fibrous materials from organic solventsInfo
- Publication number
- CA1050709A CA1050709A CA201,939A CA201939A CA1050709A CA 1050709 A CA1050709 A CA 1050709A CA 201939 A CA201939 A CA 201939A CA 1050709 A CA1050709 A CA 1050709A
- Authority
- CA
- Canada
- Prior art keywords
- alkyl
- carbon atoms
- dyeing
- dyestuff
- alkoxy
- 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.)
- Expired
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B29/00—Monoazo dyes prepared by diazotising and coupling
- C09B29/06—Monoazo dyes prepared by diazotising and coupling from coupling components containing amino as the only directing group
- C09B29/08—Amino benzenes
- C09B29/0805—Amino benzenes free of acid groups
- C09B29/0807—Amino benzenes free of acid groups characterised by the amino group
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Coloring (AREA)
Abstract
PROCESS FOR DYEING SYNTHETIC FIBROUS MATERIALS
FROM ORGANIC SOLVENTS
Abstract of the Disclosure Process for the continuous dyeing of textile materials which consist of, or contain synthetic fibres from organic solvents, wherein the said textile materials are impregnated with an organic dyeing liquor which contains at least one dyestuff of the formula
FROM ORGANIC SOLVENTS
Abstract of the Disclosure Process for the continuous dyeing of textile materials which consist of, or contain synthetic fibres from organic solvents, wherein the said textile materials are impregnated with an organic dyeing liquor which contains at least one dyestuff of the formula
Description
~0~ ;)7C3~ -The present invention relates to a process for dyeing synthetic fibrous materials from organic solvents.
According to the invention there is provided a process for the continuous dyeing of textile materials which consist of, or contain synthetic fibers from organic solvents, wherein the said textile materials are im-pregnated with an organic dyeing liquor, the boiling point of which does not exceed 150C, which contains at least one dyestuff of the formula COOR
~ N ~ N ~ N \ (1) in which R represents alkyl from S to 8 carbon atoms, Xl and X2 each represents hyclrogen, chlorine, bromine, lower alkyl, lower alkoxy, trifluoromethyl or nitro, Rl represents hydrogen, chlorine, bromine, alkyl from 1 to 4 carbon atoms, alkoxy from 1 to 4 carbon atoms, R2 represents hydrogen, chlorine, bromine, alkyl from 1 to 4 carbon atoms, alkoxy from 1 to 4 carbon atoms, acetylamino or benzoylamino,.R3 and R4 each represents hydrogen alkyl, hydroxyalkyl, cyanoalkyl, alkoxyalkyl, alkylcarbonylalkyl, alkylcarbonyl-hydroxyalkyl, alkoxycarbonyalkyl, phenyl or phenylalkyl, alkyl and alkoxy each containing from 1 to 4 carbon atoms, and subsequently exposed to a heat treatment.
The dyestufs of the invention are prepaTed in generally known 20. manner by diazotizing a diazo component of the general formula (2) COOR
~ _ NH2 (2) in which R and the substituents Xl and X2 which may be linked to the benzene ~ing are deined as above, for example, with sodium nitri.te or mineral acid or ill P
~35Q7~
with a solution of nitrosylsulfuric acid in concentrated sulfurîc acid, and coupling it with a coupling component of the gPneral formula (3) ~1 ,'',' :.
-N ~ 3 ( )
According to the invention there is provided a process for the continuous dyeing of textile materials which consist of, or contain synthetic fibers from organic solvents, wherein the said textile materials are im-pregnated with an organic dyeing liquor, the boiling point of which does not exceed 150C, which contains at least one dyestuff of the formula COOR
~ N ~ N ~ N \ (1) in which R represents alkyl from S to 8 carbon atoms, Xl and X2 each represents hyclrogen, chlorine, bromine, lower alkyl, lower alkoxy, trifluoromethyl or nitro, Rl represents hydrogen, chlorine, bromine, alkyl from 1 to 4 carbon atoms, alkoxy from 1 to 4 carbon atoms, R2 represents hydrogen, chlorine, bromine, alkyl from 1 to 4 carbon atoms, alkoxy from 1 to 4 carbon atoms, acetylamino or benzoylamino,.R3 and R4 each represents hydrogen alkyl, hydroxyalkyl, cyanoalkyl, alkoxyalkyl, alkylcarbonylalkyl, alkylcarbonyl-hydroxyalkyl, alkoxycarbonyalkyl, phenyl or phenylalkyl, alkyl and alkoxy each containing from 1 to 4 carbon atoms, and subsequently exposed to a heat treatment.
The dyestufs of the invention are prepaTed in generally known 20. manner by diazotizing a diazo component of the general formula (2) COOR
~ _ NH2 (2) in which R and the substituents Xl and X2 which may be linked to the benzene ~ing are deined as above, for example, with sodium nitri.te or mineral acid or ill P
~35Q7~
with a solution of nitrosylsulfuric acid in concentrated sulfurîc acid, and coupling it with a coupling component of the gPneral formula (3) ~1 ,'',' :.
-N ~ 3 ( )
2 ~-in which Rl, R2, R3 and R4 are defined as above, in acid to neutral, preferably aqueous medium~ optionally by adding solvents, for example, mono or bivalent alcohols, acetone or glacial acetic acid,~and, optionally, in the presence of acid-binding agents, for example, sodium acetate, magnesium carbonate or pyridine to give the dyestuffs of the general formula 1.
The dyestuffs are obtained in water-insoluble forni, they are separatedJ for example, by filtration and freed from adhering electrolytes by washing with water, Instead of a homogeneous diazo componènt a mixture of two or more diazo compon~nts may also be used. The same applies to the coupling component.
The dyestuffs to be used according to the invention dye synthetic fiber materials from organic solvents to produce dyeings which show a high dyestuff yield, a very goodbuild-up and excellent fastness properties, especially very good fastness to thermofixing, washing, rubbing and light.
Another advantage of the dyestuffs to be used according to the invention is thoir high solubility in organic solvents, for example alcohols and, in particularJ halogenated hydrocarbons, which may allow the dyeing process to be operated without using solubilizérs The dyeing liquors preferably used contain the especially valuable dyestuffs of the formula 1 mentioned above which are distinguished by an especially high solubility in organic solvents.
Mixtures of tha dyestuffs to be used according to the invention may sometimes provide better dyestuff yields than the individual dyestuffs and may also sho~ a better solubility in an organic medium.
.
.. - ~, ~ .' '.
~5C~7~
As synthetic fiber materials, materials of high-molecular-weight polyamides, polyolefins, polyacrylonitriles, polyurethanes, polyvinyl chlorides, polyvinyl aceta~es as well as cellulose - 2 1/2-acetate and cellulose triacetate, especially those of high-molecular-weight polyesters~
Such as polyethylene-glycol terephthalate, are used. The said textile materials may be used in mixtures with each other or blended with natural fibers, such as cellulosic fibers or wool.
The fibrous materials may be dyed in any processing form suitable for a continuous dyeing method, for example as tows, combed material, yarns, knit or woven fabrics or as non-woven articles.
The process of the invention is operated using organic solvents, the boiling points of which do not exceed 150C under normal conditions, for example aliphatic hydrocarbons, such as "special boiling point spirits (cuts)" (DIN [German Industrial Standards] No. 51 631/I. 59), aliphatic halogenated hydrocarbons, such as methylene chloride, dichloroethane, tri-chloroethane, tetrachloroethane, dichlorofluoromethane, dichlorotetrafluoro-ethane and octafluorocyclobutane, aromatic hydrocarbons, such as toluene and xylene, aromatic halogenated hydrocarbons, such as chlorobenzene and fluoro-benzene; especially suitable are trichlorofluoromethane, 1,2,2-trichloro-1,1,2-trifluoroethane, tetrachloroethylene, trichloroethylene and l,l,l-trichloro-ethane.
Suitable solvents are moreover, for example, alcohols, preferably aliphatic alcohols having up to ~ carbon atoms, advantageously mixtures of various solvents, especially suitable are, for example, mixtures of halogenated aliphatic hydrocarbons and aliphatic alcohols.
The padding liquor is prepared by dissolving the dyestuffs in the solvent or mixture of solvents while stirring and, where required while heating. For this purpose, the dyestuffs may be used in various forms, for example free from standardizing agents, as a concentration solution in a solvent used according to the invention or in a mixture thereof or as a 16)5~7~
composition using adju~ants ~hich are soluble in solventsJ for example oxalkylation products of fatty alcohols, alkyl-phenols, fatty acids and fatty acid amides.
The dyestuff solutions are most advantageously applied onto the material by padding but also by other impregnation methods, such as spraying, slop-padding or im~ersing.
The impregna~ion operation is preferably carried out at room temperature but it may also be performed at a lo~er or higher temperature.
Prior to the dyestuff fixation, the textile material which has been a treated with the dyeing liquor is then preferably dried, for example by treat-ing it with hot air, suctioning an inert gas (such as nitrogen) or air through it or applying superheated vapors~ for example steam or solvent vapor, or by establishing a vacuum.
Subsequently, the dyestuffs are fixed under the action of elevated temperatures, for exa~ple by means of hot air, dry heat, steam or solvent vapors.
The fixation temperatures depend on the melting points of the fibers and, in the case of a padding process, they are generally in the range of from 100 to 240C. The heat treatment may be carried out in superheated 2~ steam or in vapors of organic solvents but also with the aid of molten metals, paraffins, waxes, oxalkylation products of alcohols or fatty acids or in eutectic mixtures of salts, preferably by means of dry heat, i.e. according to the so-called Thermosol process. It is also possible to carry out the drying operation and the heat treatment in a single operation.
The solvent vapors which escape during the drying or fixing operation are generally recovered in suitable devices and the solvents thus recovered may again be used for the dyeing process of the invention.
After the dyestuffs have been fixed, the unfixed dyestuff portion, if any, is removed by a suitable aftertreatment which improves the general
The dyestuffs are obtained in water-insoluble forni, they are separatedJ for example, by filtration and freed from adhering electrolytes by washing with water, Instead of a homogeneous diazo componènt a mixture of two or more diazo compon~nts may also be used. The same applies to the coupling component.
The dyestuffs to be used according to the invention dye synthetic fiber materials from organic solvents to produce dyeings which show a high dyestuff yield, a very goodbuild-up and excellent fastness properties, especially very good fastness to thermofixing, washing, rubbing and light.
Another advantage of the dyestuffs to be used according to the invention is thoir high solubility in organic solvents, for example alcohols and, in particularJ halogenated hydrocarbons, which may allow the dyeing process to be operated without using solubilizérs The dyeing liquors preferably used contain the especially valuable dyestuffs of the formula 1 mentioned above which are distinguished by an especially high solubility in organic solvents.
Mixtures of tha dyestuffs to be used according to the invention may sometimes provide better dyestuff yields than the individual dyestuffs and may also sho~ a better solubility in an organic medium.
.
.. - ~, ~ .' '.
~5C~7~
As synthetic fiber materials, materials of high-molecular-weight polyamides, polyolefins, polyacrylonitriles, polyurethanes, polyvinyl chlorides, polyvinyl aceta~es as well as cellulose - 2 1/2-acetate and cellulose triacetate, especially those of high-molecular-weight polyesters~
Such as polyethylene-glycol terephthalate, are used. The said textile materials may be used in mixtures with each other or blended with natural fibers, such as cellulosic fibers or wool.
The fibrous materials may be dyed in any processing form suitable for a continuous dyeing method, for example as tows, combed material, yarns, knit or woven fabrics or as non-woven articles.
The process of the invention is operated using organic solvents, the boiling points of which do not exceed 150C under normal conditions, for example aliphatic hydrocarbons, such as "special boiling point spirits (cuts)" (DIN [German Industrial Standards] No. 51 631/I. 59), aliphatic halogenated hydrocarbons, such as methylene chloride, dichloroethane, tri-chloroethane, tetrachloroethane, dichlorofluoromethane, dichlorotetrafluoro-ethane and octafluorocyclobutane, aromatic hydrocarbons, such as toluene and xylene, aromatic halogenated hydrocarbons, such as chlorobenzene and fluoro-benzene; especially suitable are trichlorofluoromethane, 1,2,2-trichloro-1,1,2-trifluoroethane, tetrachloroethylene, trichloroethylene and l,l,l-trichloro-ethane.
Suitable solvents are moreover, for example, alcohols, preferably aliphatic alcohols having up to ~ carbon atoms, advantageously mixtures of various solvents, especially suitable are, for example, mixtures of halogenated aliphatic hydrocarbons and aliphatic alcohols.
The padding liquor is prepared by dissolving the dyestuffs in the solvent or mixture of solvents while stirring and, where required while heating. For this purpose, the dyestuffs may be used in various forms, for example free from standardizing agents, as a concentration solution in a solvent used according to the invention or in a mixture thereof or as a 16)5~7~
composition using adju~ants ~hich are soluble in solventsJ for example oxalkylation products of fatty alcohols, alkyl-phenols, fatty acids and fatty acid amides.
The dyestuff solutions are most advantageously applied onto the material by padding but also by other impregnation methods, such as spraying, slop-padding or im~ersing.
The impregna~ion operation is preferably carried out at room temperature but it may also be performed at a lo~er or higher temperature.
Prior to the dyestuff fixation, the textile material which has been a treated with the dyeing liquor is then preferably dried, for example by treat-ing it with hot air, suctioning an inert gas (such as nitrogen) or air through it or applying superheated vapors~ for example steam or solvent vapor, or by establishing a vacuum.
Subsequently, the dyestuffs are fixed under the action of elevated temperatures, for exa~ple by means of hot air, dry heat, steam or solvent vapors.
The fixation temperatures depend on the melting points of the fibers and, in the case of a padding process, they are generally in the range of from 100 to 240C. The heat treatment may be carried out in superheated 2~ steam or in vapors of organic solvents but also with the aid of molten metals, paraffins, waxes, oxalkylation products of alcohols or fatty acids or in eutectic mixtures of salts, preferably by means of dry heat, i.e. according to the so-called Thermosol process. It is also possible to carry out the drying operation and the heat treatment in a single operation.
The solvent vapors which escape during the drying or fixing operation are generally recovered in suitable devices and the solvents thus recovered may again be used for the dyeing process of the invention.
After the dyestuffs have been fixed, the unfixed dyestuff portion, if any, is removed by a suitable aftertreatment which improves the general
3~ astnes5 properties of the dyeings. This aftertreatment is preferably ~ -4-~56:~70~ `
carried out in the same organic solvent as already used for the dyeing, but it may also he carried out in different organic solvents or in aqueous liquors according to known methods.
The following Examples serve to illustrate the inven~ion, -the parts and percentages being by weight unless stated otherwise.
X A M P L E 1:
7 g of the dyestuff of the formula CO-0-~CH2)4-CH3 Cl - ~ - N = N - ~ - N
\ CH2-CH2-CN
were dissolved in 1 Q of perchloroethylene at room temperature. ~ls liquor was used to pad a fabric made of polyester fibers on a padding machine with a squeezing effect of 75 % ~weight of padding liquor, calculated on the weight of the goods).
The material was then dried on a suitable device and thermosoled at 210C for 1 minute. A fast yellow dyeing was obtained.
The dyestuffs had been prepared as follows: 24.2 Parts of 5-chloro-2-amino-benzoic acid amyl ester were mixed at 0 - 5C in 100 parts by volume of glacial acetic acid while stirring. 32.4 Parts of a 40 % nitrosyl sulfuric acid were added to that suspension at 0 - 5C and stirring was continued at that temperature for three hours. Towards the end of the diazotization a slight excess of nitrous acid is expected to be present.
17.4 Parts of N-ethyl-N-cyanoethyl-aniline were dissolved in 250 parts by volume of 2 N hydrochloric acid and placed in a stirring vessel.
The diazo solution of acetic acid obtained as described a~ove of 5-chloro-2-amino-benzoic acid amyl ester was introduced dropwise to that solution of the a~o component at 0 - 5C while stirring thoroughly. S~irring was continued for 1 hourl the solution was diluted with water to yield 2 Q ~nd the acid . ~ . . . . .
. . . ~ - ' . .
~alS07~
was made neutral with solid sodium acetateO At first, the dyestuff begins to precipitate in smeary form, but it completely turns to crystalline form upon stirring over night. The dyestuff is filtered off, washed with water and dried in the vacuum drying cabinet at 50C. 37 Parts of a black powder were obtained which corresponded to the dyestuff indicated in Example 1.
E X A M A-P L E 2. ~`
7 g of the dyestuff of the formula C0-0-(CH2~7~CH
Cl - ~ - N = N ~ ~ _ N ~ CH2~C~I3 ~
\ CH2-CH2-CN .' were dissolved in 1 ~ of methanol at room temperature. This liquor was used 10to pad a abric o polyester fibers on a padding machine, the squeezing ~`
effect being about 40 %, the fabric was dried, thermosoled for 1 minute at 210C and washed in cold methanol or about 5 minutes, A solid~ yellow dyeing was obtained.
The dyestuff had been prepared as follows: 28.4 Parts of 5-chloro-2-amino-benzoic acid-octyl ester were diazotized as described in Example 1 and coupled with 17.4 parts of N-ethyl-N-cyanoethyl-aniline as described in said example.
E X A M P I. E 3:
. ____ 5 g of the dyestuff of the formula CO-O- ~CH2,) 6CH3 zaN2 ~ - N = N - ~ - N ~ 2 '1=' CH2-CH3-CN
~ll)51~7~
were dissolved in 1 ~ of a mixture of 50.5 % of 1,2,2-trifluoro~trichloroethane and 49O5 % of methylene chloride at about 25C. This dyestuff solution was used to pad a fabric made~of polyester fibers on a padding machine with a squeezing effect of about 80 %, then~ the material was dried, thermosoled for 1 minute at 210C and washed for about 5 minutes in ~he same mixture of solvents in the cold state. A red, solid dyeing was obtained.
The dyestuff had been prepared as follows: 28.0 Parts of 5-nitro-2-amino-benzoic acid-heptyl ester were diazotized as described in Example 1 and coupled with 18.8 parts of N-ethyl-N-cyanoethyl-m-toluidine as described in said example.
E X A M P L E 4:
6.5 g of the dyestuff of the formula C~-0-(Ctl2)5-C~13 N2 ~ - N = N ~ ~ - N ~ 2 Ctl3 CH2-CH2-CN :' were dissolved in 1 ~ of ethanol at about 30C and applied to a fabric of polyester fibers by slop-padding. The squeezing effect was about 45 %.
After padding, the fabric was dried, thermosoled for 1 minute at 210C and after-treated in cold ethanol for 5 minutes. An orange, solid dyeing was obtained.
The dyestuff had been prepared as follows: 26.6 Parts of 5-nitro-2Q 2-amino~benzoic acid hexyl ester were diazotized as described in Example 1 and coupled with 17.4 parts of N-ethyl-N-cyanoethyl-aniline as described therein.
E X A M P L E 5:
5 g of the dyestuff of the formula ~ .
. .
~C~5~
.. ...
( 2)7 3 2~ N = 11 -~3_N~ 2 2 z '.
.
were dissolved in 1 Q of isopropanol at about 30C. This liquor was used to pad a fabric made of polyester fibers on a padding machine wi~h a squeezing effect of about 40 %, the material was dried, thermosoled for 1 minute at 210C and washed in cold isopropanol for about 5 minutes. A red, solid dyeing was obtained.
The dyestuff had been prepared as follows: 2904 Parts of 5-nitro-2-amino~benzoic acid octyl ester were diazotized as described in Bxample 1 and coupled with 19.3 parts oE N,N-Coxethyl-n-butyl)-aniline as described in said example.
E X A M P L E 6:
carried out in the same organic solvent as already used for the dyeing, but it may also he carried out in different organic solvents or in aqueous liquors according to known methods.
The following Examples serve to illustrate the inven~ion, -the parts and percentages being by weight unless stated otherwise.
X A M P L E 1:
7 g of the dyestuff of the formula CO-0-~CH2)4-CH3 Cl - ~ - N = N - ~ - N
\ CH2-CH2-CN
were dissolved in 1 Q of perchloroethylene at room temperature. ~ls liquor was used to pad a fabric made of polyester fibers on a padding machine with a squeezing effect of 75 % ~weight of padding liquor, calculated on the weight of the goods).
The material was then dried on a suitable device and thermosoled at 210C for 1 minute. A fast yellow dyeing was obtained.
The dyestuffs had been prepared as follows: 24.2 Parts of 5-chloro-2-amino-benzoic acid amyl ester were mixed at 0 - 5C in 100 parts by volume of glacial acetic acid while stirring. 32.4 Parts of a 40 % nitrosyl sulfuric acid were added to that suspension at 0 - 5C and stirring was continued at that temperature for three hours. Towards the end of the diazotization a slight excess of nitrous acid is expected to be present.
17.4 Parts of N-ethyl-N-cyanoethyl-aniline were dissolved in 250 parts by volume of 2 N hydrochloric acid and placed in a stirring vessel.
The diazo solution of acetic acid obtained as described a~ove of 5-chloro-2-amino-benzoic acid amyl ester was introduced dropwise to that solution of the a~o component at 0 - 5C while stirring thoroughly. S~irring was continued for 1 hourl the solution was diluted with water to yield 2 Q ~nd the acid . ~ . . . . .
. . . ~ - ' . .
~alS07~
was made neutral with solid sodium acetateO At first, the dyestuff begins to precipitate in smeary form, but it completely turns to crystalline form upon stirring over night. The dyestuff is filtered off, washed with water and dried in the vacuum drying cabinet at 50C. 37 Parts of a black powder were obtained which corresponded to the dyestuff indicated in Example 1.
E X A M A-P L E 2. ~`
7 g of the dyestuff of the formula C0-0-(CH2~7~CH
Cl - ~ - N = N ~ ~ _ N ~ CH2~C~I3 ~
\ CH2-CH2-CN .' were dissolved in 1 ~ of methanol at room temperature. This liquor was used 10to pad a abric o polyester fibers on a padding machine, the squeezing ~`
effect being about 40 %, the fabric was dried, thermosoled for 1 minute at 210C and washed in cold methanol or about 5 minutes, A solid~ yellow dyeing was obtained.
The dyestuff had been prepared as follows: 28.4 Parts of 5-chloro-2-amino-benzoic acid-octyl ester were diazotized as described in Example 1 and coupled with 17.4 parts of N-ethyl-N-cyanoethyl-aniline as described in said example.
E X A M P I. E 3:
. ____ 5 g of the dyestuff of the formula CO-O- ~CH2,) 6CH3 zaN2 ~ - N = N - ~ - N ~ 2 '1=' CH2-CH3-CN
~ll)51~7~
were dissolved in 1 ~ of a mixture of 50.5 % of 1,2,2-trifluoro~trichloroethane and 49O5 % of methylene chloride at about 25C. This dyestuff solution was used to pad a fabric made~of polyester fibers on a padding machine with a squeezing effect of about 80 %, then~ the material was dried, thermosoled for 1 minute at 210C and washed for about 5 minutes in ~he same mixture of solvents in the cold state. A red, solid dyeing was obtained.
The dyestuff had been prepared as follows: 28.0 Parts of 5-nitro-2-amino-benzoic acid-heptyl ester were diazotized as described in Example 1 and coupled with 18.8 parts of N-ethyl-N-cyanoethyl-m-toluidine as described in said example.
E X A M P L E 4:
6.5 g of the dyestuff of the formula C~-0-(Ctl2)5-C~13 N2 ~ - N = N ~ ~ - N ~ 2 Ctl3 CH2-CH2-CN :' were dissolved in 1 ~ of ethanol at about 30C and applied to a fabric of polyester fibers by slop-padding. The squeezing effect was about 45 %.
After padding, the fabric was dried, thermosoled for 1 minute at 210C and after-treated in cold ethanol for 5 minutes. An orange, solid dyeing was obtained.
The dyestuff had been prepared as follows: 26.6 Parts of 5-nitro-2Q 2-amino~benzoic acid hexyl ester were diazotized as described in Example 1 and coupled with 17.4 parts of N-ethyl-N-cyanoethyl-aniline as described therein.
E X A M P L E 5:
5 g of the dyestuff of the formula ~ .
. .
~C~5~
.. ...
( 2)7 3 2~ N = 11 -~3_N~ 2 2 z '.
.
were dissolved in 1 Q of isopropanol at about 30C. This liquor was used to pad a fabric made of polyester fibers on a padding machine wi~h a squeezing effect of about 40 %, the material was dried, thermosoled for 1 minute at 210C and washed in cold isopropanol for about 5 minutes. A red, solid dyeing was obtained.
The dyestuff had been prepared as follows: 2904 Parts of 5-nitro-2-amino~benzoic acid octyl ester were diazotized as described in Bxample 1 and coupled with 19.3 parts oE N,N-Coxethyl-n-butyl)-aniline as described in said example.
E X A M P L E 6:
4 g of the dyestuff of the formula C0 0 (CH2)4 3 _ N = N - ~ N ~ 2 3 ~ \ CH2-CH2-cN ;~
were dissolved in 1 Q of perchloroethylene a~ room temperature. This liquor was used to pad a fabric of polyester fibers on a padding machine with a squeezing effect of about 80 %, the material was dried thereafter. To fix the dyestuff, one half of the material was thermosoled for 1 minute at 215C, the other half was steamed for about 30 minutes at 1.5 atmg. Yellow, solid dyeings were obtained in both cases. A similar Tesult could be obtained when l'''`';`' .
, 7~ ~
the dyestuff wasfixedin overheated perchloroethylene steam (at about 150C
for 10 - 15 minutes) instead of water steam.
The dyestuff had been prepared as follows: 20.7 Parts of 2-amino-benzoic acid amyl ester were diazotized as described in Example 1 and coupled with 17.4 parts of N-ethyl-N-~yanoethyl-aniline as described in said example.
E X A M P L E 7:
__ ______ :
4 g of the dyestuff of the formula Co-o-(cH2)7cH3 Cl - ~ - N = N - ~ ~ CH2-CH3 H2-cN
Cl CH3 were dissolved in 1 ~ o a mixture of 50 % by volume of methylene chloride 1~ and 50 % by volume of 1,2,2-trifluorotrichloroethane at room temperatureO
~is liquor was used to pad a fabric made of polyester fibers on a padding machine with a squeezing effect of about 75 %, the material was dried and thermosoled for 1 minute at 210C. A golden-yellow, solid dyeing was obtained.
The dyestuff had been prepared as follows: 31.8 Parts of 2~amino-3,5-dichloro-benzoic acid-octyl ester were diazotized as described in Bxample 1 and coupled with 18.8 parts of N-ethyl-N-cyanoethyl-m-toluidine as described therein.
E X A M P L E 8:
_ _ _ _ .
were dissolved in 1 Q of perchloroethylene a~ room temperature. This liquor was used to pad a fabric of polyester fibers on a padding machine with a squeezing effect of about 80 %, the material was dried thereafter. To fix the dyestuff, one half of the material was thermosoled for 1 minute at 215C, the other half was steamed for about 30 minutes at 1.5 atmg. Yellow, solid dyeings were obtained in both cases. A similar Tesult could be obtained when l'''`';`' .
, 7~ ~
the dyestuff wasfixedin overheated perchloroethylene steam (at about 150C
for 10 - 15 minutes) instead of water steam.
The dyestuff had been prepared as follows: 20.7 Parts of 2-amino-benzoic acid amyl ester were diazotized as described in Example 1 and coupled with 17.4 parts of N-ethyl-N-~yanoethyl-aniline as described in said example.
E X A M P L E 7:
__ ______ :
4 g of the dyestuff of the formula Co-o-(cH2)7cH3 Cl - ~ - N = N - ~ ~ CH2-CH3 H2-cN
Cl CH3 were dissolved in 1 ~ o a mixture of 50 % by volume of methylene chloride 1~ and 50 % by volume of 1,2,2-trifluorotrichloroethane at room temperatureO
~is liquor was used to pad a fabric made of polyester fibers on a padding machine with a squeezing effect of about 75 %, the material was dried and thermosoled for 1 minute at 210C. A golden-yellow, solid dyeing was obtained.
The dyestuff had been prepared as follows: 31.8 Parts of 2~amino-3,5-dichloro-benzoic acid-octyl ester were diazotized as described in Bxample 1 and coupled with 18.8 parts of N-ethyl-N-cyanoethyl-m-toluidine as described therein.
E X A M P L E 8:
_ _ _ _ .
5 g of the dyestuff o~ the formula C0-0-(CH2)6-CH3 N 2 ~ _ N = N - ~ ~ ~12-CH2-\=:/ CH2-CH2-0-CO-CH3 ~, .
`"' , _ g _ .~........ ~ .
were dissolved in 1 ? of trichloroethylene at about 25°C. this liquor wasused to pad a fabric made of polyester fibers on a padding machine with a squeezing effect of about 70%. After padding the material was dried and thermosoled for 1 minute at 210°C. An orange solid dyeing was obtained.
The dyestuff had been prepared as follows: 28.0 Parts of 2-amino-t-nitro-benzoic acid heptyl ester were diasotized as described in Example 1 and coupled with 23.2 parts of N,N-acetoxethyl-cyanoethyl)-aniline as described in said exaple.
E X A M P L E S:
5 g of the dyestuff of the formula were dissolved in 1 ? of methylene chloride at room temperatue. This liquor was used to pad a fabric made of polyester fibers on a padding machine with a squeezing effect of about 65%, the material was dried and thermosoled for 1 minute at 210°C. A red violet, solid dyeing was obtained.
The dyestuff had been prepared as follows: 26.6 Parts of 2-amino-t-nitro-benzoic acid hexyl ester were diasotized as described in Example 1 and coupled with 226 parts of 3-phenyl-amino-acetanilide as described in said exaple.
E X A M P L E S:
10 g of the dyestuff of the formula ~3507C99 were dissol~ed in 1 Q of 1~2,2-trifluorotrichloroe~hane at 25C. This liquor was used to pad a fabric made of polyester fibers on a padding machine with a squeezing effect of 75 %. After padding the material was dried, thermosoled for 1 minute at 210C and washed for about 5 minutes in cold 1,2,2-trifluoro-trichloroethane. A red, solid dyeing was obtained.
The dyestuff had been prepared as follows: 26.6 Parts of 2-amino-5-nitro-benzoic acid hexyl ester were diazotized as described in Example 1 and coupled with 23.5 parts of N,N-~acetoxyethyl-n-butyl~-aniline as described in said example.
E X A M P L E ll:
a ~
8 g of the dyestuff of the formula CO-~-~CH2)6-CH3 ~ ;
N 2 ~ N = N ~ ~ C~l2-C~I3 were dissolved in 1 Q of perchloroethylene at room temperature. This liquor -was used to pad a fabric made of polyester, polyamide 6, polyamide 6,6-cellulosetriacetate and cellulose 2 1/2-acetate, a yarn made of polyvinyl chloride fibers and combed material made of polypropylene fibers on a padding machine.
The squeezing effects were within the range of 70 to 90 % depending on the material.
Then, the textile materials were dried, steamed for 30 minutes at 2a about 1.5 atmg (PVC: 40 minutes at 102 - 103C) and after-treated in cold perchloroethylene for about 10 minutes. Orange, solid dyeings were obtained ~;
in all cases.
The dyestuff had been prepared as follows: 26,6 Parts of 2-amino-5-nitro-ben70ic acid hexyl ester were diazoti~ed as described in Example 1 and coupled with 17~4 parts of N-ethyl-N-cyanoethyl-aniline as indicated therein.
.
9 : -E X A M P L E 12:
3 g Q~' the dyestuff of the formula C0-O-(CH2)5-CH3 N = N ~ ~ _ N ~ 2 2 ~A) Cl and 5 g of the dyestuff of the formula Co-o-(cH2)4cH3 NO2 ~ - N = N - ~ ~ CH2-C~I3 (B) ~ CH2-CH2-CN
were dissolved in 1 ~ of methanol at room temperature. This liquor was used to pad a fabric made of polyester fibers on a padding machine wi~h a squeezing effect of about 40 %. The material was dried, ~hersoled for 1 minute at 210C and washed cold in a mixture consisting of equal parts by volume of 1,2,2-trifluoro-trichloroethane and methylene chloride for 5 minutes. An o~ange solid dyeing was obtained.
The two dyestuffs had been prepared as follows:
A) 27.0 Parts of 2-amino-4-chloro-benzoic acid hexyl ester were diazotized as described in Example 1 and coupled with 19.0 parts of N-cyanoe~hyl-N-oxethyl-aniline as described therein.
B) 25.2 Parts of 2-amino-5-nitro-benzoic acid amyl ester were diazotized as described in Example 1 and coupled with 17.4 parts of N-ethyl-N-cyanoethyl-aniline as indicated in said example.
E ~ A M P L E 13-.
4 g of the dyestuff of the formula ~5~7~
~ 2)6 3 ¦ ~A) NO2 ~ _ N = N ~ ~ N ~' H2 C~3 =1/ ~ CH2-CH2-CN
Br and 4 g of the dyestuff of the formula ~ -CH3-~CH2)4-O-CO- ~ N = N - ~ - N- CH2-CH3 (B~
' were dissolved in 1 ~ of perchloroethylene at about 25C. This liquor was used to pad a fabric made of polyester fibers, polyamide 6, polyamide 6,6 and cellulose triacetate fibers on a padding machine. The squeezing effects were within the range of from 65 to 80% depending on the material. After padding, the fabrics were dried, thermosoled for 1 minute at 190C ~polyamide and cellulose triacetate) or at 210C ~polyester) and washed for about 5 minutes in perchloroethylene in cold state. In all casesJ yellow solid dyeings were obtained.
The two dyestuffs had been prepared as follous:
A~ 35.9 Parts of 2-amino-3-bromo-5-nitro-benzoic acid heptyl ester were diazotized as described in Example 1 and coupled with 17.4 parts of N-ethyl-N-cyanoethyl-aniline as described in said example.
B) 2Q.7 Parts of 4-amino-benzoic acid amyl ester were pas~ed with 60 parts by volume of 5 N hydrochloric acid and filled with water to a total volume of 150 parts by volume. 20 parts by volume oE 5 N sodium nitrite solutian were slowly added dropwise at a tempera~ure of O - 2C while thoroughly stirring. After finishing the addition of the above solution, .
.
~05C17~
stirring was continued at 0 - 2C for 1 hour with an excess of nitrous acid.
Then, the excess of nit~ous acid was destroyed by amidosulfonic acid and the diazo solution was filtered.
The diazo solution so obtained was added dropwise to a hydrochloric solution of 17.4 parts of N-ethyl-N-cyanoethylaniline in the manner described as to the coupling of Example 1 and after-treated as described in said example.
E X A M P L E 14:
10 g of ~he dyestuff of the formula C0 (CH2)7 CH3 2 ~ - N = N - ~ ~ ~ CH2-CH2-H ~ ~
~CH2-CBr=CH2 "
:
were dissolved in 1 ~ of perchloroethylene at room temperatureO This liquor was used to pad a blended fabric of 67 % of polyester fibers and 33 % of cotton on a padding machine with a~squeezing effect of about 85 %, the material was dried, thermosoled for 1 minute at 210C and washed cold for 5 minutes in perchloroethyleneO An orange, solid dyeing was obtained on the polyester portion of the blended fabric.
The dyestuf had been prepared as follows: 2904 Parts of 2-amino-5-nitro-benzoic acid octyl ester were diazotized as described in Example 1 and coupled with 25.6 parts of N-~-oxethyl-N-~-bromo-allyl-aniline as described in said example.
2Q E X A M P L E 15:
__ _ _ . _ _ _ 3 g of the dyestuff of the formula c0-0-~CH2)7C~13 N = N - ~ / 2 C 3 CH -CH -CN
~s~o~ :
were dissolved in 1 9~ of l,l,l-trichloroethane at room temperature. This dyestuff solution was used to pad a fabric made of polyester fibers on a padding machine. The squeezing effect was about 75%, the material was dried and thermosoled for 1 minute at 210C. A yellow, solid dyeing was obtained.
The dyestuff had been prepared as follows: 24.9 Parts of 2-amino-benzoic acid octyl ester were diazotized as described in Example 1 and coupled with 17.4 parts of N-ethyl-N-cyanoethyl-aniline as described in said example.
E X A M P L E 16:
10 g of the dyestuff of the for~ula C0-0-(CH2~7-CH3 - N = N ~ ~ N ~ CH2-CH2-CH2-CH
CH2-CH2-OH :
Cl were dissolved in 1 9. of a mixture of 70 % by volume of perchloro-ethylene and 30 % by volume of methanol at 25C. This liquor was used to pad a fabric made of polyester fibers on a padding machine with a squeezing effect of 7Q %, the material was dried, thermosoled for 1 minute at 210 C and washed for 5 minutes in the same mixture of solvents. A yellow, solid dyeing was obtained.
The dyestuff had been prepared as follows: 28.4 Parts of 2-amino-4-chloro-benzoic acid octyl ester were diazotized, as described in Example 1 and coupled with 1~,3 parts of N,N-~oxethyl-n-butyl)-aniline as described in the same example.
E X A M P L E 17:
7 g o the dyestuff of the formula r ~ 1 5 .:' , . , , : . . :
.. . ,. . . . . . ~ , ~ ` -CO-O-~CH2)4 CH3 Cl ~ _ N = N - ~ ~ CH2-CH
~ .
Cl : ,, WeTe dissolved in 1 Q of perchloroethylene at room temperature. This liquor was used to pad a fabric of polyester fibers on a padding machine with a squeezing effect of about 80 %, the fabric was dried, thermosoled for 1 minute at 210C and after-treated with the same solvent in cold state for abOut 5 minutes. A golden-yellow~ solid dyeing was obtained.
A similar result could be obtained when methanol was used instead o perchloroethylene. In this case, the squeezing efect was about 40 %.
The dyestuff had been prepared as follows: 27.6 Parts of 2-amino-3,5-dichlorobenzoic acid acid-amyl ester were diazotized, as described in Example 1 and coupled with 17.4 parts of N-ethyl-N-cyanoethyl-aniline as described in said example.
The following Table contains a list of further dyestuffs used in accordance with the invention which yield solid dyeings on polyester fibers in the shades indicated therein when dyed according to the prescriptions of Examples 1 to ]7.
,
`"' , _ g _ .~........ ~ .
were dissolved in 1 ? of trichloroethylene at about 25°C. this liquor wasused to pad a fabric made of polyester fibers on a padding machine with a squeezing effect of about 70%. After padding the material was dried and thermosoled for 1 minute at 210°C. An orange solid dyeing was obtained.
The dyestuff had been prepared as follows: 28.0 Parts of 2-amino-t-nitro-benzoic acid heptyl ester were diasotized as described in Example 1 and coupled with 23.2 parts of N,N-acetoxethyl-cyanoethyl)-aniline as described in said exaple.
E X A M P L E S:
5 g of the dyestuff of the formula were dissolved in 1 ? of methylene chloride at room temperatue. This liquor was used to pad a fabric made of polyester fibers on a padding machine with a squeezing effect of about 65%, the material was dried and thermosoled for 1 minute at 210°C. A red violet, solid dyeing was obtained.
The dyestuff had been prepared as follows: 26.6 Parts of 2-amino-t-nitro-benzoic acid hexyl ester were diasotized as described in Example 1 and coupled with 226 parts of 3-phenyl-amino-acetanilide as described in said exaple.
E X A M P L E S:
10 g of the dyestuff of the formula ~3507C99 were dissol~ed in 1 Q of 1~2,2-trifluorotrichloroe~hane at 25C. This liquor was used to pad a fabric made of polyester fibers on a padding machine with a squeezing effect of 75 %. After padding the material was dried, thermosoled for 1 minute at 210C and washed for about 5 minutes in cold 1,2,2-trifluoro-trichloroethane. A red, solid dyeing was obtained.
The dyestuff had been prepared as follows: 26.6 Parts of 2-amino-5-nitro-benzoic acid hexyl ester were diazotized as described in Example 1 and coupled with 23.5 parts of N,N-~acetoxyethyl-n-butyl~-aniline as described in said example.
E X A M P L E ll:
a ~
8 g of the dyestuff of the formula CO-~-~CH2)6-CH3 ~ ;
N 2 ~ N = N ~ ~ C~l2-C~I3 were dissolved in 1 Q of perchloroethylene at room temperature. This liquor -was used to pad a fabric made of polyester, polyamide 6, polyamide 6,6-cellulosetriacetate and cellulose 2 1/2-acetate, a yarn made of polyvinyl chloride fibers and combed material made of polypropylene fibers on a padding machine.
The squeezing effects were within the range of 70 to 90 % depending on the material.
Then, the textile materials were dried, steamed for 30 minutes at 2a about 1.5 atmg (PVC: 40 minutes at 102 - 103C) and after-treated in cold perchloroethylene for about 10 minutes. Orange, solid dyeings were obtained ~;
in all cases.
The dyestuff had been prepared as follows: 26,6 Parts of 2-amino-5-nitro-ben70ic acid hexyl ester were diazoti~ed as described in Example 1 and coupled with 17~4 parts of N-ethyl-N-cyanoethyl-aniline as indicated therein.
.
9 : -E X A M P L E 12:
3 g Q~' the dyestuff of the formula C0-O-(CH2)5-CH3 N = N ~ ~ _ N ~ 2 2 ~A) Cl and 5 g of the dyestuff of the formula Co-o-(cH2)4cH3 NO2 ~ - N = N - ~ ~ CH2-C~I3 (B) ~ CH2-CH2-CN
were dissolved in 1 ~ of methanol at room temperature. This liquor was used to pad a fabric made of polyester fibers on a padding machine wi~h a squeezing effect of about 40 %. The material was dried, ~hersoled for 1 minute at 210C and washed cold in a mixture consisting of equal parts by volume of 1,2,2-trifluoro-trichloroethane and methylene chloride for 5 minutes. An o~ange solid dyeing was obtained.
The two dyestuffs had been prepared as follows:
A) 27.0 Parts of 2-amino-4-chloro-benzoic acid hexyl ester were diazotized as described in Example 1 and coupled with 19.0 parts of N-cyanoe~hyl-N-oxethyl-aniline as described therein.
B) 25.2 Parts of 2-amino-5-nitro-benzoic acid amyl ester were diazotized as described in Example 1 and coupled with 17.4 parts of N-ethyl-N-cyanoethyl-aniline as indicated in said example.
E ~ A M P L E 13-.
4 g of the dyestuff of the formula ~5~7~
~ 2)6 3 ¦ ~A) NO2 ~ _ N = N ~ ~ N ~' H2 C~3 =1/ ~ CH2-CH2-CN
Br and 4 g of the dyestuff of the formula ~ -CH3-~CH2)4-O-CO- ~ N = N - ~ - N- CH2-CH3 (B~
' were dissolved in 1 ~ of perchloroethylene at about 25C. This liquor was used to pad a fabric made of polyester fibers, polyamide 6, polyamide 6,6 and cellulose triacetate fibers on a padding machine. The squeezing effects were within the range of from 65 to 80% depending on the material. After padding, the fabrics were dried, thermosoled for 1 minute at 190C ~polyamide and cellulose triacetate) or at 210C ~polyester) and washed for about 5 minutes in perchloroethylene in cold state. In all casesJ yellow solid dyeings were obtained.
The two dyestuffs had been prepared as follous:
A~ 35.9 Parts of 2-amino-3-bromo-5-nitro-benzoic acid heptyl ester were diazotized as described in Example 1 and coupled with 17.4 parts of N-ethyl-N-cyanoethyl-aniline as described in said example.
B) 2Q.7 Parts of 4-amino-benzoic acid amyl ester were pas~ed with 60 parts by volume of 5 N hydrochloric acid and filled with water to a total volume of 150 parts by volume. 20 parts by volume oE 5 N sodium nitrite solutian were slowly added dropwise at a tempera~ure of O - 2C while thoroughly stirring. After finishing the addition of the above solution, .
.
~05C17~
stirring was continued at 0 - 2C for 1 hour with an excess of nitrous acid.
Then, the excess of nit~ous acid was destroyed by amidosulfonic acid and the diazo solution was filtered.
The diazo solution so obtained was added dropwise to a hydrochloric solution of 17.4 parts of N-ethyl-N-cyanoethylaniline in the manner described as to the coupling of Example 1 and after-treated as described in said example.
E X A M P L E 14:
10 g of ~he dyestuff of the formula C0 (CH2)7 CH3 2 ~ - N = N - ~ ~ ~ CH2-CH2-H ~ ~
~CH2-CBr=CH2 "
:
were dissolved in 1 ~ of perchloroethylene at room temperatureO This liquor was used to pad a blended fabric of 67 % of polyester fibers and 33 % of cotton on a padding machine with a~squeezing effect of about 85 %, the material was dried, thermosoled for 1 minute at 210C and washed cold for 5 minutes in perchloroethyleneO An orange, solid dyeing was obtained on the polyester portion of the blended fabric.
The dyestuf had been prepared as follows: 2904 Parts of 2-amino-5-nitro-benzoic acid octyl ester were diazotized as described in Example 1 and coupled with 25.6 parts of N-~-oxethyl-N-~-bromo-allyl-aniline as described in said example.
2Q E X A M P L E 15:
__ _ _ . _ _ _ 3 g of the dyestuff of the formula c0-0-~CH2)7C~13 N = N - ~ / 2 C 3 CH -CH -CN
~s~o~ :
were dissolved in 1 9~ of l,l,l-trichloroethane at room temperature. This dyestuff solution was used to pad a fabric made of polyester fibers on a padding machine. The squeezing effect was about 75%, the material was dried and thermosoled for 1 minute at 210C. A yellow, solid dyeing was obtained.
The dyestuff had been prepared as follows: 24.9 Parts of 2-amino-benzoic acid octyl ester were diazotized as described in Example 1 and coupled with 17.4 parts of N-ethyl-N-cyanoethyl-aniline as described in said example.
E X A M P L E 16:
10 g of the dyestuff of the for~ula C0-0-(CH2~7-CH3 - N = N ~ ~ N ~ CH2-CH2-CH2-CH
CH2-CH2-OH :
Cl were dissolved in 1 9. of a mixture of 70 % by volume of perchloro-ethylene and 30 % by volume of methanol at 25C. This liquor was used to pad a fabric made of polyester fibers on a padding machine with a squeezing effect of 7Q %, the material was dried, thermosoled for 1 minute at 210 C and washed for 5 minutes in the same mixture of solvents. A yellow, solid dyeing was obtained.
The dyestuff had been prepared as follows: 28.4 Parts of 2-amino-4-chloro-benzoic acid octyl ester were diazotized, as described in Example 1 and coupled with 1~,3 parts of N,N-~oxethyl-n-butyl)-aniline as described in the same example.
E X A M P L E 17:
7 g o the dyestuff of the formula r ~ 1 5 .:' , . , , : . . :
.. . ,. . . . . . ~ , ~ ` -CO-O-~CH2)4 CH3 Cl ~ _ N = N - ~ ~ CH2-CH
~ .
Cl : ,, WeTe dissolved in 1 Q of perchloroethylene at room temperature. This liquor was used to pad a fabric of polyester fibers on a padding machine with a squeezing effect of about 80 %, the fabric was dried, thermosoled for 1 minute at 210C and after-treated with the same solvent in cold state for abOut 5 minutes. A golden-yellow~ solid dyeing was obtained.
A similar result could be obtained when methanol was used instead o perchloroethylene. In this case, the squeezing efect was about 40 %.
The dyestuff had been prepared as follows: 27.6 Parts of 2-amino-3,5-dichlorobenzoic acid acid-amyl ester were diazotized, as described in Example 1 and coupled with 17.4 parts of N-ethyl-N-cyanoethyl-aniline as described in said example.
The following Table contains a list of further dyestuffs used in accordance with the invention which yield solid dyeings on polyester fibers in the shades indicated therein when dyed according to the prescriptions of Examples 1 to ]7.
,
Claims (8)
PROPERTY OR PRIVILEGE IS CLAIMED ARE DEFINED AS FOLLOWS:
1. Process for the continuous dyeing of textile materials which con-sist of, or contain synthetic fibers from organic solvents, wherein the said textile materials are impregnated with an organic dyeing liquor, the boiling point of which does not exceed 150°C, which contains at least one dyestuff of the formula in which R represents alkyl from 5 to 8 carbon atoms, X1 and X2 each repre-sents hydrogen, chlorine, bromine, lower alkyl, lower alkoxy, trifluoromethyl or nitro, R1 represents hydrogen, chlorine, bromine, alkyl from 1 to 4 carbon atoms, alkoxy from 1 to 4 carbon atoms, R2 represents hydrogen, chlorine, bromine, alkyl from 1 to 4 carbon atoms, alkoxy from 1 to 4 carbon atoms, acetylamino or benzoylamino, R3 and R4 each represents hydrogen, alkyl, hy-droxyalkyl, cyanoalkyl, alkoxyalkyl, alkylcarbonylalkyl, alkylcarbonyl-hydroxy-alkyl, alkoxycarbonylalkyl, phenyl or phenylalkyl, alkyl and alkoxy each con-taining from 1 to 4 carbon atoms, and subsequently exposed to a heat treatment.
2. A process as claimed in claim 1, wherein the fibrous materials are impregnated with a dyeing liquor containing a mixture of dyestuffs of the formulae indicated in claim 1.
3. A process as claimed in claim 1 or 2, wherein the organic solvent of the dyeing liquor represents a halogenated hydrocarbon.
4. A process as claimed in claim 1 or 2, wherein the organic solvent of the dyeing liquor represents an aliphatic alcohol.
5. A process as claimed in claim 1 or 2, wherein the organic solvent of the dyeing liquor represents a mixture of halogenated hydrocarbons and/or aliphatic alcohols.
6. A process as claimed in claim 1 or 2, wherein the dyeings obtained are after-treated in an organic solvent.
7. A process as claimed in claim 1 or 2, wherein the dyeings obtained are after-treated in the same organic solvent or mixture of organic solvents which had been applied in the dyeing process.
8. A process as claimed in claim 1 or 2, wherein as textile material a material consisting of polyester fibres is dyed.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19732329388 DE2329388A1 (en) | 1973-06-08 | 1973-06-08 | PROCESS FOR COLORING SYNTHETIC FIBER MATERIALS FROM ORGANIC SOLVENTS |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1050709A true CA1050709A (en) | 1979-03-20 |
Family
ID=5883525
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA201,939A Expired CA1050709A (en) | 1973-06-08 | 1974-06-07 | Process for dyeing synthetic fibrous materials from organic solvents |
Country Status (7)
| Country | Link |
|---|---|
| JP (1) | JPS5031183A (en) |
| BE (1) | BE816121A (en) |
| CA (1) | CA1050709A (en) |
| DE (1) | DE2329388A1 (en) |
| FR (1) | FR2232636B1 (en) |
| GB (1) | GB1459464A (en) |
| IT (1) | IT1014834B (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5266227A (en) * | 1991-02-22 | 1993-11-30 | Basf Aktiengesellschaft | Oil-soluble phenylazoaniline dyes |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB2171110A (en) * | 1985-02-16 | 1986-08-20 | Yorkshire Chemicals Plc | Monoazo disperse dyes |
| US5382659A (en) * | 1988-05-10 | 1995-01-17 | Ciba-Geigy Corp. | Aromatic acids |
| DE58909302D1 (en) * | 1988-05-10 | 1995-07-27 | Ciba Geigy Ag | Aromatic acids. |
| DE4120362A1 (en) * | 1991-06-20 | 1992-12-24 | Basf Ag | THIAZOLAZO DYES WITH A CLUTCH COMPONENT FROM THE DIPHENYLAMINE RANGE |
| DE4343823A1 (en) * | 1993-12-22 | 1995-06-29 | Basf Ag | Use of azo dyes for marking hydrocarbons as well as new azo dyes |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CH517813A (en) * | 1969-09-01 | 1972-01-15 | Basf Ag | Red water-insol azo dyes for cellulose - esters and/or linear synthetic polyesters |
| GB1351126A (en) * | 1970-04-29 | 1974-04-24 | Yorkshire Chemicals Ltd | Colouration process |
| DE2053712A1 (en) * | 1970-11-02 | 1972-05-10 | Farbenfabriken Bayer Ag, 5090 Leverkusen | Monoazo dyes - prepd from 4-amino benzoic esters and n,n-diethyl n'-benzoyl m-phenylene diamine, for hydrophobic fibres |
-
1973
- 1973-06-08 DE DE19732329388 patent/DE2329388A1/en active Pending
-
1974
- 1974-06-06 IT IT2368974A patent/IT1014834B/en active
- 1974-06-06 JP JP49063484A patent/JPS5031183A/ja active Pending
- 1974-06-07 CA CA201,939A patent/CA1050709A/en not_active Expired
- 1974-06-10 BE BE145243A patent/BE816121A/en unknown
- 1974-06-10 FR FR7419995A patent/FR2232636B1/fr not_active Expired
- 1974-06-10 GB GB2557074A patent/GB1459464A/en not_active Expired
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5266227A (en) * | 1991-02-22 | 1993-11-30 | Basf Aktiengesellschaft | Oil-soluble phenylazoaniline dyes |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS5031183A (en) | 1975-03-27 |
| IT1014834B (en) | 1977-04-30 |
| FR2232636A1 (en) | 1975-01-03 |
| FR2232636B1 (en) | 1978-05-26 |
| DE2329388A1 (en) | 1975-01-16 |
| GB1459464A (en) | 1976-12-22 |
| BE816121A (en) | 1974-12-10 |
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