US3748091A

US3748091A - Process for dyeing polyester textiles

Info

Publication number: US3748091A
Application number: US00132183A
Authority: US
Inventors: D Fawkes
Original assignee: Imperial Chemical Industries Ltd
Current assignee: Imperial Chemical Industries Ltd
Priority date: 1970-04-22
Filing date: 1971-04-07
Publication date: 1973-07-24
Anticipated expiration: 1990-07-24
Also published as: GB1340049A; BE765909A; FR2086255B1; NL7105365A; DE2119674A1; FR2086255A1

Abstract

PROCESS FOR DYEING OR OPTICALLY BRIGHTENING CELLULOSE TRIACETATE AND AROMATIC POLYESTER TEXTILE MATERIALS WHICH COMPRISES TREATING SAID TEXTILE MATERIALS WITH A DISPERSION OF A DYESTUFF OR OPTICALLY BRIGHTENING AGENT WHICH CONTAINS AT LEAST ONE OPTIONALLY SUBSTITUTED CARBONAMIDO OR SULPHONAMIDO GROUP IN A HALOGENATED HYDROCARBON AND IN THE PRESENCE OF A SMALL AMOUNT OF WATER, THE SAID TREATMENT BEING CARRIED OUT AT A TEMPERATURE ABOVE THE BOILING POINT OF THE AZEOTROPE OF THE HALOGENATED HYDROCARBON AND THE WATER, AND AT A PRESSURE ABOVE ATMOSPHERIC PRESSURE.

Description

United States Patent 3 748 091 PROCESS FOR uYEnsG lOLYESTER TEXTILES David Melville Fawkes, Manchester, England, assignor to Imperial Chemical Industries Limited, London, England N0 Drawing. Filed Apr. 7, 1971, Ser. No. 132,183

3,748,091 Patented July 24, 1973 h tile materials, it is preferred to give the dyed textile mate- Claims priority, applicatlion2 Great Britain, Apr. 22, 1970,

/7o Int. (:1. D06p 1/20 US. Cl. 8-39 6 Claims ABSTRACT OF THE nrscLosUna the presence of a small amount of water, the said treatment being carried out at a temperature above the boiling point of the azeotrope of the halogenated hydrocarbon and the Water, and ate pressure above atmospheric pressure. i

This invention relates to an improved process for the dyeing or optical brightening of cellulose triacetate and aromatic polyester textile materials and their blends with other textile materials.

It has previously been proposed to dye or optically brighten synthetic textile materials at elevated temperatures with solutions or dispersions of water insoluble dyestuffs or optically brightening agents in a chlorinated-hydrocarbon solvent, especially perchloroethylene, optionally containing small amounts of water, the said treatment being optionally carried out at pressure above atmospheric pressure. This process suffers from the disadvantage that the affinity of the said dyestuffs or optically brightening agents is low, so' that only pale shades can be achieved by this process. a

(It has now been found that aparticularly valuable class of dyestuffs or optically brightening agents which can be used are those which are insoluble or only slightly soluble in the chlorinated hydrocarbon and which contain at least one optionally substituted carbonamido (CONH or sulphonamido (SO NH groupv as, under these particular methods of application, this class of dyestuffs or optically brightening agents has a much higher afiinity an improved process for dyeing or optically brightening cellulose triacetate and aromatic polyester textile material a treatment in a clearing bath comprising an emulsion of an aqueous alkaline solution of sodium hydrosulphite in perchloroethylene.

The amount of water present in the dyeing process is preferably between 0.2% and 5% based on the volume of the halogenated hydrocarbon.

Although the dyeing process is carried out at a temperature above the boiling point of the azeotrope of the halogenated hydrocarbon and the water, it is preferred that the temperature be equal to or greater than the boiling point of the pure halogenated hydrocarbon.

As examples of halogenated hydrocarbons which can be used in the process of the invention either singly or in the form of mixtures there may be mentioned chloroform, carbon tetrachloride, dibromoethylene, trichloroethylene, 1:l:Z-trichloro-lz2z2-trifiuoroethane, 1:1:1 trichloroethane, and preferably tetrachloroethylene, (perchloroeth ylene).

There can also be present emulsifying agents which can be anionic, cationic or non-ionic. Non-ionic emulsifying agents may be, for example (a) polyethers of hydroxy,

mercapto and amino compounds such as polyalkoxy-fatty alcohols, polyalkoxy polyols, polyalkoxy-mercaptans,

polyalkoxy aliphatic amines, polyalkoxy alkylphenols,

face Active Agents by Elworthy, Florenceand Macfar lane, published 'by Chapman and Hall Ltd., in 1968.

The dyestuffs and optical brightening agents which can be used in the process of the invention can be of any of the recognised classes of dyestuffs, for example, methine, styryl, phthalocyanine, phthaloperinone, quinphthalone, azo, anthraquinone and nitro dyestuffs, and optical brightening agents, for example stilbenes, coumarins, pyrazolines, naphthalimides, carbostyryls, 1:3:4 oxodiazoles,

rials which comprises treating said textile materials with w a dispersion of a dyestuif or optically brightening agent which contains at least one optionally substituted carbonamido or sulphonamido group in a halogenated hydrocarbon and in the presence of a small amount of water,-

the said treatment being carried out at a temperature above the boiling point of the azeotrope of the halogenated hydrocarbon and the water, and at a pressure above atmospheric pressure.

The process of the invention can be conveniently carried out by immersing the textile material in a dispersion of v the said dyestuif or optical brightening agent in the haloof the azeotrope of the halogenated hydrocarbon and the water. At the conclusion of the process the dyed or optically brightened textile material may be rinsed with the brightening agent or is attached thereto through an alkylene or an alkyleneamino radical. Such groups can be conveniently represented by the formula:

wherein X represents '-CO or -SO and R and R each independently represent a hydrogen atom or an optionally substituted alkyl, cycloalkyl, aryl or heterocyclic radical, or R and R are joined together to form with 3 4 the nitrogen atom N a 5- or -6-membered nitrogen-conparts of perchloroethylene in the presence of 0.1 part, taining heterocyclic ring. as deflocculating agent, of the polyurea product prepared As examples of the radicals represented by R and R as described below. 2 parts of water are added, the mixthere are mentioned lower alkyl such as methyl, ethyl, ture is placed in a deying vessel and 20 parts of polyethylpropyl and butyl, substituted lower alkyl for example hy- 5 one terephthalate textile material in the form of staple droxy lower alkyl such as fi-hydroxyethyl, lower alkoxy cloth is immersed in the mixture. The dyeing vessel is then lower alkyl such as fi-methoxyethyl and 'y-methoxypropyl, sealed and heated at 120 C., for 30 minutes to effect dyecyano lower alkyl such as fi-cyanoe hyl, aryl Su s it e ing. The dyed textile material is then removed from the lower alkyl such as benzyl, cyclohexyl, optionally substipressure vessel, rinsed in acetone to remove the excess dyetllted P 3 Such as P y itself and tolyl, y Chlo- 10 bath liquor and any loosely bound dyestufl, and is finally rophenyl and bromophenyl. dried. The textile material is thereby coloured a deep yel- AS examples of the atld fi-membefed nitfogelPcOH- lowish-orange shade of excellent fastness properties. mining hetefocyclic Tings formed y lointflg together R1, The polyurea product used in the above example was it R and the nitrogen atom N there may be mentioned lf b i d as f llows; Py indolinfi, Piperidine, morpholine, PiPeYaZine A solution of 73.7 parts of a commercially available and N-alkylpiperazine. 40% solution in butyl acetate of polymerised mixed 2:4- It is however Pmtermt1 that R1 and R2 each represent and 2:6-tolylenediisocyanates containing 5.7% of isocyaa hydrogen atom. nate groups and less than 0.5% of free tolylene diisocya- The Said dyestutfs and Optical bl'ightehing agehts can nate in 32 parts of acetone was added to a stirred soluthemselves be Obtalhed y any of the Convehhohal math tion of 53.5 parts of a fatty secondary amine derived from Dds 0 P g dyestutf? i oPticatbl'ightehihg {agents soya and commercially available under the trade name from intermediates containing the sa1d carbonam1de or Armeen is a registered trademark) in 11 P F E t h r gmggd g fg g gf i ga2 parts of acetone at 50 to 55 C. The acetone was then groups 111 0 e P e P YP removed by distillation under reduced pressure.

include for exam le:

(a) Treating a dyestuif or optical brightening agent 25 In Place of the dyestuff s d in Example 1 ther e with chlorosulphonic acid and reacting the resulting suldyestuffs obtained by dlazohslhg the phonchloride with the appropriate amine amines listed in the second column of the following table (b) Reacting a dyestuif or optical brightening agent h cohphng the reuttlllg dlflZO f P S mm the 0011- containing a carboxylic acid group or groups with thionyl P components llsted 111 rd 60 1111111 of the table.

chloride and treating the resulting acid chloride with the The fourth ol mn 0f the table lists the shades of the appropriate amine. resulting dyeings.

Example Amine Coupling component shade 4- nob nzene sul honamide.-. N:N- i(flhy r xy hyl)aniline-.-..- Yellowidh-oran e. i e p N-methyl-N-(fi-hydroxyethyDaniline. Do. g 4 d N-methyl-N-(fl-eyanoethyl)aniline..- Yellow. 5 do N-ethyl-N-(fl:v-dihydroxyprcpybanili Yellowish-orange. 6 taminolgenzene ea{bgnarnbixdgs.find-r. .15.33... Nzbgdi(5-hydroxyethyl)-mrt0lu1d1ne Do.

7-.. amino enzene so onoxye y am a o.

8 2-ehloro-4-nitroanilihe "Y 3-sulphonamido-N:N-didthydroxyethybaniline Bluish-red.

(c) Reacting together intermediates which give a dye- EXAMPLE 9 stulf or optical brightening agent (for example a diazo OJ part of the monoazo dyestuff obtained by coupling component and a coupling component) at least one of which contains a carbonamide or sulphonamido group.

The dispersion of the dyestuff or optical brightening agent in the halogenated hydrocarbon can be conveniently obtained by milling or grinding the dyestufi or optical brightening agent in the halogenated hydrocarbon in the presence of a defiocculating agent. As deflocculating agents there may be mentioned, for example, polyureas which are essentially free from basic amino groups and which contain at least two urea groups and at least two groups each of which is an alkyl, alkenyl or alkapolyenyl group containing at least eight carbon atoms, and which are soluble in organic solvents.

The cellulose triacetate and aromatic polyester, espe- 1y bound dyestufi and 15 then dried A deep yellow shade cially polyethyleneterephthalate, textile materials can be of excellent fastness Properties is thereby obtainedin the form of fibres or filaments or knitted or woven EXAMPLE 1() oods. If desired the said textile materials can be in the v f orm of blends with other textile materials particularly gg g ifig ggfii g333 1352 3 55 gif cotton and woollen textlle materials diazotised 3-chloro-4-aminobenzenesulphonamide with N- When applied to synthetic textile materials by the prOcmethyl-N-(fl-cyanoethyl)aniline, and the dyemg 18 then ess of the 1nvent1on the said dyestuffs and optical bright carried out for 3 0 minutes at 120 C. A p orange y ening agents have excellent afiinity thus enabling heavy depths of shades to be obtained, and the resulting dyed mg of excellent fastness propertles Obtamed' or optically brightened textile materials have excellent EXAMPLE 11 i to the tests commonly applied to Such textile 0.1 part of the dyestufi obtained by coupling diazotised ma 4-aminobenzenesulphonamide with N-methyl-N- -c ano- 1 i mventlfn fif fi g notdhmltedtby the ethyl)aniline is dispersed in 320 parts of perchlorh th y lene Y es m w c t a par 8 an Percen ages are Y containing 0.05 part of the polyurea described in Example welght' EXAMPLE 1 1. 2 parts of water are added, the mixture placed in a dyeing vessel and 20 parts of cellulose triacetate fabric are 0.2 part of the monoazo dyestufi obtained by coupling immersed in the liquid. The vessel is sealed and dyeing diazotised 4-aminobenzenesulphonamide with N-ethyl-N- carried out for 30 minutes at C. The dyed material is (p-hydroxyethynaniline is dispersed by milling in 800 75 then removed from the dyebath, rinsed in aqueous ethanol,

diazotised 4-aminobenzenesulphonamide with N:N-di(;3- cyanoethyl)aniline is dispersed by milling in 320 parts of perchloroethylene containing 0.05 part of the polyurea obtained as described in Example 1 above. 2 parts of water are then added, and the resulting mixture placed in a dyeing vessel. 20 parts of a polyester fibre which is commercially available under the trade name of Crimplene (Crimplene is a registered trademark) are then immersed in the mixture, the dyeing vessel is sealed, and dyeing then carried out for 30 minutes at C. The dyed textile material is then removed from the vessel, rinsed in acetone to remove excess dyebath liquor and any looseand is dried. A deep yellow shade of excellent fastness properties is obtained.

The following table gives further examples which illustrate the invention, the dyestuff used in Example 10 being replaced by the dyestuffs obtained by diazotising the amines listed in the second column of the table and coupling with the coupling components listed in the third column of the table. The fourth column of the table gives the shades of the resulting dyeings.

wherein X represents --SO and R and R each independently represent hydrogen, lower alkyl, hydroxy lower alkyl, lower alkoxy lower alkyl or cyano lower alkyl in a halogenated hydrocarbon and in the presence of between 0.2% and 5% water based on the volume of the halogenated hydrocarbon, said treatment being carried out at a temperature above the boiling point of the azeotrope of the halogenated hydrocarbon and the Water, and at a pressure above atmospheric pressure.

Example Amine 12 4-amgnobenzeuesulphonamide 14 3-nitro-4-aminobenzensulphonamide N-rnethyl-N-(fi-cyanoethyl)ani N:N-di(fl-cyanoethyl)aniline 3-chlor0-4-aminobenzenesulphon-N-(fi-chloroethyDami e d 4-aminobanzensulphon-N-(B-chloroethyl)amide 2-amino-5-nitrobenzamide Coupling component 1-ethyl-3-eyano-4-methy1 6-hydroxypyrid-2'0ne N-methyl-N-(fl-cyanoethyD-mflgoluidine.

Shade Greenish-yellow. Orange.

line

do do N-methyl-N-(B-cyanoethyl) aniline 2aminobenzthiazole-fi-sulphonamide do do N :N -di (dcyanoethyl) aniline do -m-toluidine 22 2-amino-5-nitrobenzenesulphon-N-methylamide. cyanoethyDani 'ne 23-.-. do N2N-di(fi-cyanoethybauiline 24 4-nitr ili 2-naphthylamine-5-sulphonamide 25 2chloro-4-nitr do Red. 26 2-cyano-4-nitroaniline--- do Bluish-red. 27 2-chloro-4-nitr0am'line Z-naphthylamineA-sulphonamide Reddish-viol'w.

do Z-Baphthylaminel-sulphon-N-(B-hydroxyethyDamide Violet. a-methoxyaniline u N-ethyl-N-(fi-carbamoylethyl)aniline Orange 2-carboxy-4mtroan1l1ne N-methyl-N-(fl-carbamoyletliyl)aniline Violet Z-methylsulphonylt-nitroanilin Bluish-red. 2-cyano4-nitroaniline .do Do. 33 do B-acetylamino-N-methyl-N-(B-earbamoylethyl)aniline.. Bluish-vio et. 34 2-am1no-5-mtroth1az0le N-(B-cyanoethyl)-N-(fl-carbamoylethyl)aniline-.. Blue. 35 2-arninohenzthiazole-(i-methylsulphone N-ethyl-N-(B-carbamoylethyl)-m-t0luidine Red. 36 -mtrnanilma N-methybN-(Bsulphamoylethyl) aniline. Red.

N-ethyl-N-(B-sulphamoylethyl)-m-toluidine Bluish-re'l. 38 2-cyano-4-n1troaniline d0 Violet. 39.. 2:4-din1tro-6-bromoaniline 2-eth0xy-5-acetylamino-N-(Bsulpham0ylethyl)an1l1ne- Blue.

EXAMPLE 40 2. Process as claimed in claim 1 wherein the halo In place of the 0.1 part of dyestuff used in Example there is used 0.1 part of 1:4-diaminoanthraquinone-Z-carbonamide or of 1:4-diaminoanthraquinone-Z-carbo-N:N- di(/8-hydroxyethyl)amide or of l-amino 4 (p-hydroxyaniline) anthraquinone 2 carbonamide whereby reddishblue, reddish-blue and blue dyeings respectively are obtained of excellent fastness properties.

EXAMPLE 41 0.01 part of the fluorescent brightening agent 1:4-di-(4- carbamoylstyryl)benzene is milled in 320 parts of perchloroethylene containing 0.005 part of the polyurea described in Example 1. 2 parts of water are added, the mixture placed in a dyeing vessel, parts of an aromatic polyester fabric are added, the vessel sealed and then heated for minutes at 120 C. The fabric is then removed from the vessel, rinsed in perchloroethylene and dried. The fabric is brighter than the untreated fabric.

EXAMPLE 42 genated hydrocarbon is perchloroethylene.

3. Process as claimed in claim 1 wherein the dispersion contains a deflocculating agent.

4. Process as claimed in claim 1 wherein the dispersion contains an emulsifying agent.

5. Process as claimed in claim 1 wherein the dyestuff is an azo dyestuff which contains at least one unsubstituted sulphonamido group directly attached to a carbon atom of an aryl radical or attached thereto through an alkylene or alkyleneamino radical.

6. Process as claimed in claim 1 wherein the dyestuif is an anthraquinone dyestuff which contains at least one unsubstituted sulphonamido group directly attached to a carbon atom of an aryl radical or attached thereto through an alkylene or alkyleneamino radical.

References Cited UNITED STATES PATENTS 3,622,558 11/1971 Kolliker et a1. 850 X 3,623,834 11/1971 Seuret et a1. 8-62 X 2,725,390 11/1955 Fogelman et a1 8-173 X 3,623,833 11/1971 Wildermuth et a1 8--40 FOREIGN PATENTS 1,192,984 5/ 1970 Great Britain 8-174 1,535,352 6/1968 France 8174 OTHER REFERENCES Ciba-Geigy Review, 1971/4, pp. 11-13.-

LEON D. ROSDOL, Primary Examiner T. J. HERBERT, JR., Assistant Examiner US. Cl. X.R. 841 C, 174