EP0036252A2 - Verfahren zum Bedrucken von Textilien - Google Patents

Verfahren zum Bedrucken von Textilien Download PDF

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Publication number
EP0036252A2
EP0036252A2 EP81300721A EP81300721A EP0036252A2 EP 0036252 A2 EP0036252 A2 EP 0036252A2 EP 81300721 A EP81300721 A EP 81300721A EP 81300721 A EP81300721 A EP 81300721A EP 0036252 A2 EP0036252 A2 EP 0036252A2
Authority
EP
European Patent Office
Prior art keywords
disperse
dyestuffs
dyestuff
alkali
carboxylic acid
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.)
Granted
Application number
EP81300721A
Other languages
English (en)
French (fr)
Other versions
EP0036252A3 (en
EP0036252B1 (de
Inventor
John Reginald Provost
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Imperial Chemical Industries Ltd
Original Assignee
Imperial Chemical Industries Ltd
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Imperial Chemical Industries Ltd filed Critical Imperial Chemical Industries Ltd
Priority to AT81300721T priority Critical patent/ATE11310T1/de
Publication of EP0036252A2 publication Critical patent/EP0036252A2/de
Publication of EP0036252A3 publication Critical patent/EP0036252A3/en
Application granted granted Critical
Publication of EP0036252B1 publication Critical patent/EP0036252B1/de
Expired legal-status Critical Current

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Classifications

    • DTEXTILES; PAPER
    • D06TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06PDYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
    • D06P3/00Special processes of dyeing or printing textiles, or dyeing leather, furs, or solid macromolecular substances in any form, classified according to the material treated
    • D06P3/34Material containing ester groups
    • D06P3/52Polyesters
    • D06P3/54Polyesters using dispersed dyestuffs
    • DTEXTILES; PAPER
    • D06TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06PDYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
    • D06P5/00Other features in dyeing or printing textiles, or dyeing leather, furs, or solid macromolecular substances in any form
    • D06P5/12Reserving parts of the material before dyeing or printing ; Locally decreasing dye affinity by chemical means
    • DTEXTILES; PAPER
    • D06TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06PDYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
    • D06P5/00Other features in dyeing or printing textiles, or dyeing leather, furs, or solid macromolecular substances in any form
    • D06P5/15Locally discharging the dyes
    • D06P5/151Locally discharging the dyes with acids or bases

Definitions

  • This invention relates to an improved process for the resist or discharge printing of synthetic textile materials.
  • Resist printing is a method of textile printing in which an undyed textile material is first printed with a substance (the resist) which prevents the uptake or fixation of a subsequently applied dyestuff, so that there is obtained a white pattern on a coloured ' ground, or a pattern of contrasting colour to the ground by incorporating suitable dyestuffs or colour-producing substances in the resist print paste.
  • a substance the resist
  • Discharge printing is a method of textile printing in which dyed textile material is printed with a chemical composition (the discharge) that destroys the dyestuff locally to give a white pattern, or in which a second dyestuff, applied simultaneously with the discharge, produces a pattern of contrasting colour.
  • United Kingdom Patent Specification No. 1543724 describes and claims a process for producing discharge printing effects in a coloured ground shade on a synthetic textile material, which comprises applying to that area of the material where the ground shade and the discharge effect are wanted one or more disperse dyes which contain at least one carbcxylic ester group but are free from carboxylic acid and sulphonic acid groups, and in a separate stage applying to the material where the discharge effect is wanted a printing paste which is alkaline or beccmes alkaline on heating or steaming and which does not contain any reducing agent, thereafter heating or steaming the material and thereafter washing the material.
  • stages 1 and 3 can be reversed, so that the dyestuff is applied to the textile material before the alkaline print paste.
  • stage 5 in which the textile material is subjected to the action of heat or steam, the disperse dyestuff in contact with the alkali is converted into a water-soluble form, whilst the disperse dyestuff which is not in contact with the alkali is fixed on the textile material.
  • the water-soluble form of the dyestuff is then removed from the textile material by the washing treatment of stage 6.
  • stage 2 it would be desirable if, in the above process, the first drying operation (stage 2) could be eliminated so that stage 1 is followed immediately by stage 3.
  • This "wet-on-wet" process would have the advantages that the process has one stage less, with consequent saving in crying plant occupation time, and also the saving in the energy used to effect drying.
  • wet-on-wet resist or discharge prints having sharp definition between the different coloured areas of the print can be obtained if the alkali used in the print paste is sodium or potassium silicate.
  • a process for producing resist or discharge printing effects on a synthetic textile material which comprises applying to the textile material, in either order and without drying the textile material between the applications, (i) an .alkaline printing paste containing sodium or potassium silicate, and which may contain one or more disperse dyestuffs free from sulphonic acid, carboxylic acid and carboxylic acid ester groups, the said dyestuffs being unaffected by alkali at the concentration present, and (ii) a printing paste or padding liquor containing at least one alkali dischargeable disperse dyestuff free frrm sulphonic acid and carboxylic acid groups and free from carboxylic acid ester groups which if hydrolysed would leave carboxylic acid groups attached to the dyestuff molecule, thereafter heating or steaming the material and thereafter washing the material.
  • an .alkaline printing paste containing sodium or potassium silicate, and which may contain one or more disperse dyestuffs free from sulphonic acid, carboxylic acid and carboxylic acid ester
  • the alkali-dischargeable dyestuffs which are used in the process according to the present invention may be broadly classified as follows:-A.
  • Dyestuffs which contain one or more lactone rings which open in the presence of alkali with formation of the water-soluble alkali metal salts of the corresponding hydroxy carboxylic acid. Opening of the lactone ring may be accompanied by destruction of the chromophoric system of the dyestuff.
  • Examples of this class are the dyestuff of the formula: which is disclosed in German Offenlegungsschrift 2440405, and the dyestuff of formula: which is disclosed in UK Patent Specification No.1568231.
  • unsymmetrically substituted compounds having the abeve-disclosed formulae may be obtained by reaction of equimolar quantities of hydroquinone and a compound of formula: wherein A is hydroxyl, 0-acyl or halogen; B is hydrogen, lower alkyl or aryl and R is phenyl which may carry one or more substituents, for example, lower alkyl, lower alkoxy, hydroxy, chlorine or bromine.
  • A is hydroxyl, 0-acyl or halogen
  • B is hydrogen, lower alkyl or aryl
  • R is phenyl which may carry one or more substituents, for example, lower alkyl, lower alkoxy, hydroxy, chlorine or bromine.
  • lower alkyl and “lower alkoxy” mean alkyl and alkoxy groups respectively which contain 1 to 4 carbon atoms.
  • reaction may be carried out either in the absence of a solvent or in the presence of a high boiling solvent such as di- or tri-chlorobenzene to give the intermediate of formula: which is subsequently reacted with a compound of formula: wherein A and B have the previously defined meanings and R 1 is phenyl which may carry one or more substituents, R 1 being different to R, to give a compound of formula: which is then oxidised, preferably in situ by using nitrobenzene as reaction solvent or by treatment with an oxidising agent such as hydrogen peroxide in acetic acid, to give the desired dyestuff of formula:
  • dyestuffs in class A which may be used in the present process are those which contain the coumarin ring system.
  • Methine dyestuffs containing at least one group for example the dyestuff of formula: which is disclosed in French Patent Specification No.1551030, and the dyestuff of formula: which is disclosed in US Patent Specification No.2850520.
  • Azo dyestuffs derived from anilines having at least two electron-withdrawing groups ortho and/or para to the amino group as diazo components and para-coupling amine coupling components,for example the first two of which are disclosed in UK Patent Specification No.852493, and the last in UK Patent Specification No.1050675.
  • Dyestuffs containing groups which are capable of water-soluble salt formation in the presence of strong alkali including azopyridone dyestuffs and dyestuffs containing phenolic hydroxyl groups or primary or secondary sulphonamide groups, for example: and both of which are disclosed in UK Patent Specification No.1256093; the dyestuff of formula: which is disclosed in UK Patent Specification No.1398741; the dyestuff of formula: which is C.I.
  • Disperse Yellow 42 the dyestuff of formula: which is disclosed in UK Patent Specification No.1016246; the anthraquinone dyestuff of formula: which is disclosed in French Patent Specification No.1371626, and the pyridone dyestuffs of formulae: both of which are disclosed in UK Patent Specification No.1095829
  • Azo dyestuffs derived from 2-amino-5-nitrothiazole as diazo component and a para-coupling amine as coupling component for example the dyestuffs of formulae: which are all disclosed in UK Patent Specification No.723933; the dyestuff of formula: which is disclosed in US Patent Specification No.2790791, and the dyestuff of formula: which is disclosed in UK Patent Specification No.840903,
  • miscellaneous dyestuffs C.I. Disperse Violet 88, C.I. Disperse Yellow 180, C.I. Disperse Violet 48, C.I. Disperse Blue 92, C.I. Disperse Yellow 93, C.I. Disperse Yellow 201, C.I. Disperse Yellow 88, C.I. Disperse Yellow 210, C.I. Disperse Red 203 and C.I. Disperse Yellow 202.
  • dyestuffs which may be used in the present process are those which discharge only partially (i.e. do not give a white discharge) and which do not leave a wcak enough stain to allow all shades of illumination to be used, but which do show an even residual shade that allows the use of such dyestuffs for limited illuminated shades and which may be used for shading purposes.
  • Class A which may be prepared as described previously for similar dyestuffs in Class A.
  • miscellaneous dyestuffs of formulae which is disclosed in UK Patent Specification No.859899, and which is disclosed in UK Patent Specification No.1027968, together with C.I. Disperse Red 72, C.I. Disperse Blue 139, C.I. Disperse Orange 55, C.I. Disperse Red 329 and C.I. Disperse Violet 40.
  • Any dyestuff which undergoes chromophore destruction in the presence of alkali to an extent such as to make it suitable for a ground shade in discharge printing may be used in the present process.
  • the sodium silicate which is used in the above process may be any of those grades of sodium silicate which are commercially available and is preferably a sodium silicate in which the molecular ratio of SiO 2 to Na 2 0 is from 1.65:1.0 to 4.0:1.0.
  • the potassium silicate which is used preferably has a molecular ratio of Si0 2 to K 2 0 of from 2.0:1 to 4.0:1.
  • the amount of sodium or potassium silicate which is used in the printing paste (i) must provide sufficient alkali to discharge the disperse dyestuff in the padding liquor or printing paste (ii), and may be from 50 tp 300 parts by weight per 1000 parts by weight of printing paste.
  • a sodium or potassium silicate having a high molecular ratio of SiO 2 to N a2 0 or K 2 O can be-replaced in the printing paste by a smaller quantity of sodium or potassium silicate having a lower molecular ratio of Si0 2 to Na 2 0 or K 2 0, without affecting the result.
  • the printing paste containing the sodium or potassium silicate must also contain a humectant such as ethylene glycol urea or, preferably, glycerol, a dye solvent such as polyethylene glycol. for example,'a polyethylene glycol having a molecular weight in the region of 300, and a thickening agent.
  • a humectant such as ethylene glycol urea or, preferably, glycerol
  • a dye solvent such as polyethylene glycol. for example,'a polyethylene glycol having a molecular weight in the region of 300
  • a thickening agent are starch derivatives such as starch ethers, carob-seed gum ethers, m odified carboxymethylcelluloses and combinations of these, optionally in admixture with a water-in-oil or oil- in-water emulsion.
  • the padding liquor or print paste used to apply the alkali-dischargcable disperse dyestuff should also contain a carboxylic acid, for example, citric acid, to prevent premature interaction of the dyestuff with the alkaline sodium or potassium silicate, and a thickener such as one of those thickeners already mentioned above.
  • a carboxylic acid for example, citric acid
  • a thickener such as one of those thickeners already mentioned above.
  • adjuvants which are conventionally employed in the application of disperse dycstuffs to synthetic textile materials from such media, for example, carriers, fixation assistants, level dyeing assistants, dispersing agents and antifoam agents.
  • the heat treatment to which the textile material is subjected after the application of the print paste containing the sodium or potassium silicate and the print paste or padding liquor containing the disperse dyestuff can comprise a heat treatment for a short period at temperatures from 150° to 220°C. It is, however, preferred to subject the textile material to a steaming'treatment, for example, saturated steam at 100°C for a few minutes followed by a dry heat treatment at 160° to 220°C or superheated steam at 150° to 200°C, or the use of saturated steam under pressure at 115° to 150°C.
  • the synthetic textile materials used in the process of the invention can be in the form of non-woven fabric, felt, woven or knitted goods, or carpets.
  • synthetic textile materials there may be mentioned secondary cellulose acetate and cellulose triacetate, polypropylene, acrylic, polyamide, and preferably aromatic polyester textile materials.
  • the synthetic textile material can be in the form of a blend or union with a cellulose textile material, for example a polyethyleneterephthalate/cotton blend or union.
  • the alkali-dischargeable disperse dyestuff can be used together with a reactive dye whose reactive groups, such as sulphatoethylsulphone groups, form a dye-fibre bond with the hydroxyl groups of the cellulose textile material which is hydrolysed under the alkaline conditions in those areas where the alkaline print paste is applied, or a reactive dyestuff containing one or more phosphonic acid groups which does not fix on cellulose in the presence of alkali.
  • a reactive dye whose reactive groups, such as sulphatoethylsulphone groups, form a dye-fibre bond with the hydroxyl groups of the cellulose textile material which is hydrolysed under the alkaline conditions in those areas where the alkaline print paste is applied, or a reactive dyestuff containing one or more phosphonic acid groups which does not fix on cellulose in the presence of alkali.
  • the disperse dyestuff or dyestuffs which are optionally used in the alkaline printing paste containing sodium or potassium silicate can be any of the disperse dyestuffs not adversely affected by alkali which are conventionally employed in colouring synthetic textile materials. Examples of such dyestuffs are given in, for example, the Third Editipn of the Colour Index which was published in 1971.
  • a resist print paste comprising: is printed on to a woven polyethylene terephthalate textile material, and without drying the textile material is then coated over all, including that part which has already been printed with the above resist paste, with the following print paste comprising:
  • the textile material is then dried on drying cylinders for 2 minutes at approximately 95°C, high temperature steamed at 170°C, for 8 minutes, washed off using the six-stage washing sequence described above and finally dried.
  • the resulting blue on white pattern has excellent definition.
  • sodium silicate used in the above example is replaced by the same amount of a sodium silicate in which the molecular ratio of Si0 2 to Na 2 O is 1.65:1.0 a similar result is obtained; the amount of this latter sodium silicate can also be reduced to 100 parts without adverse effect on the sharpness of the resulting print.

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  • Engineering & Computer Science (AREA)
  • Textile Engineering (AREA)
  • Chemical & Material Sciences (AREA)
  • Dispersion Chemistry (AREA)
  • Coloring (AREA)
EP19810300721 1980-03-13 1981-02-20 Verfahren zum Bedrucken von Textilien Expired EP0036252B1 (de)

Priority Applications (1)

Application Number Priority Date Filing Date Title
AT81300721T ATE11310T1 (de) 1980-03-13 1981-02-20 Verfahren zum bedrucken von textilien.

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
GB8008597 1980-03-13
GB8008597 1980-03-13
GB8014139 1980-04-29
GB8014139 1980-04-29

Publications (3)

Publication Number Publication Date
EP0036252A2 true EP0036252A2 (de) 1981-09-23
EP0036252A3 EP0036252A3 (en) 1981-11-18
EP0036252B1 EP0036252B1 (de) 1985-01-16

Family

ID=26274812

Family Applications (1)

Application Number Title Priority Date Filing Date
EP19810300721 Expired EP0036252B1 (de) 1980-03-13 1981-02-20 Verfahren zum Bedrucken von Textilien

Country Status (4)

Country Link
EP (1) EP0036252B1 (de)
DE (1) DE3168222D1 (de)
ES (1) ES500294A0 (de)
PT (1) PT72662B (de)

Cited By (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0051261A1 (de) * 1980-10-31 1982-05-12 CASSELLA Aktiengesellschaft Verfahren zur Herstellung von Ätzreservedrucken auf Textilmaterialien
EP0121875A2 (de) * 1983-04-07 1984-10-17 BASF Aktiengesellschaft Verfahren zur Herstellung alkalisch ätzbarer Färbungen und Drucke
EP0209120A2 (de) * 1985-07-18 1987-01-21 Yoshida Kogyo K.K. Verfahren zur Markierung von Haftverschlusselementen
AU568577B2 (en) * 1983-10-31 1988-01-07 Allied Corporation A master cylinder
EP0293745A2 (de) * 1987-06-03 1988-12-07 BASF Aktiengesellschaft Verfahren zur Herstellung von Ätzdrucken
EP0416888A2 (de) 1989-09-05 1991-03-13 Wace Uk Limited Bedrucken von Textilmaterialien
ITSA20120006A1 (it) * 2012-05-10 2013-11-11 Oz Anadolu Kimya Sanayi Ve Ticaret Anonim Sirketi Innovazione nelle paste corrodenti per la stampa tessile.

Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2322323A (en) * 1941-04-16 1943-06-22 Celanese Corp Discharge printing of textiles
GB1481741A (en) * 1973-08-16 1977-08-03 Hoechst Ag Process for producing multicolour effects on textile materials
GB1481742A (en) * 1973-08-16 1977-08-03 Hoechst Ag Process for producing irregular shadow dyeings on polyester fibres and mixtures thereof
GB1512321A (en) * 1976-01-05 1978-06-01 Ici Ltd Colouration process for cellulose textile materials
GB1543724A (en) * 1975-08-13 1979-04-04 Ici Ltd Process for the production of discharge printing effects on synthetic textile materials
GB2028383A (en) * 1978-08-19 1980-03-05 Cassella Ag Process for dyeing and printing synthetic hydrophobic fibre material
EP0023080A1 (de) * 1979-07-18 1981-01-28 Imperial Chemical Industries Plc Substituierte 2,7-Dioxo-2,7-dihydrobenzo(1,2b;5,6-b1)-difuran oder -dipyrrol-Farbstoffe, Verfahren zu ihrer Herstellung und ihre Verwendung zum Färben von Textilmaterialien aus aromatischen Polyestern

Patent Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2322323A (en) * 1941-04-16 1943-06-22 Celanese Corp Discharge printing of textiles
GB1481741A (en) * 1973-08-16 1977-08-03 Hoechst Ag Process for producing multicolour effects on textile materials
GB1481742A (en) * 1973-08-16 1977-08-03 Hoechst Ag Process for producing irregular shadow dyeings on polyester fibres and mixtures thereof
GB1543724A (en) * 1975-08-13 1979-04-04 Ici Ltd Process for the production of discharge printing effects on synthetic textile materials
GB1512321A (en) * 1976-01-05 1978-06-01 Ici Ltd Colouration process for cellulose textile materials
GB2028383A (en) * 1978-08-19 1980-03-05 Cassella Ag Process for dyeing and printing synthetic hydrophobic fibre material
EP0023080A1 (de) * 1979-07-18 1981-01-28 Imperial Chemical Industries Plc Substituierte 2,7-Dioxo-2,7-dihydrobenzo(1,2b;5,6-b1)-difuran oder -dipyrrol-Farbstoffe, Verfahren zu ihrer Herstellung und ihre Verwendung zum Färben von Textilmaterialien aus aromatischen Polyestern

Cited By (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0051261A1 (de) * 1980-10-31 1982-05-12 CASSELLA Aktiengesellschaft Verfahren zur Herstellung von Ätzreservedrucken auf Textilmaterialien
EP0121875A2 (de) * 1983-04-07 1984-10-17 BASF Aktiengesellschaft Verfahren zur Herstellung alkalisch ätzbarer Färbungen und Drucke
EP0121875A3 (de) * 1983-04-07 1984-12-19 BASF Aktiengesellschaft Verfahren zur Herstellung alkalisch ätzbarer Färbungen und Drucke
AU568577B2 (en) * 1983-10-31 1988-01-07 Allied Corporation A master cylinder
EP0209120A2 (de) * 1985-07-18 1987-01-21 Yoshida Kogyo K.K. Verfahren zur Markierung von Haftverschlusselementen
EP0209120A3 (en) * 1985-07-18 1988-01-07 Yoshida Kogyo K.K. Method of providing marks on surface-type fasteners
EP0293745A2 (de) * 1987-06-03 1988-12-07 BASF Aktiengesellschaft Verfahren zur Herstellung von Ätzdrucken
EP0293745A3 (de) * 1987-06-03 1991-08-14 BASF Aktiengesellschaft Verfahren zur Herstellung von Ätzdrucken
EP0416888A2 (de) 1989-09-05 1991-03-13 Wace Uk Limited Bedrucken von Textilmaterialien
EP0416888A3 (en) * 1989-09-05 1991-12-11 John Green & Son Plc Printing of fabrics
ITSA20120006A1 (it) * 2012-05-10 2013-11-11 Oz Anadolu Kimya Sanayi Ve Ticaret Anonim Sirketi Innovazione nelle paste corrodenti per la stampa tessile.

Also Published As

Publication number Publication date
EP0036252A3 (en) 1981-11-18
PT72662A (en) 1981-04-01
PT72662B (en) 1982-03-19
EP0036252B1 (de) 1985-01-16
ES8207251A1 (es) 1982-09-01
DE3168222D1 (en) 1985-02-28
ES500294A0 (es) 1982-09-01

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