EP0021011B1 - Verfahren zum Entfernen von Oligomerenablagerungen auf textilen Materialien - Google Patents
Verfahren zum Entfernen von Oligomerenablagerungen auf textilen Materialien Download PDFInfo
- Publication number
- EP0021011B1 EP0021011B1 EP80102715A EP80102715A EP0021011B1 EP 0021011 B1 EP0021011 B1 EP 0021011B1 EP 80102715 A EP80102715 A EP 80102715A EP 80102715 A EP80102715 A EP 80102715A EP 0021011 B1 EP0021011 B1 EP 0021011B1
- Authority
- EP
- European Patent Office
- Prior art keywords
- liquor
- fibers
- polyester
- oligomers
- dyeing
- 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
Links
Classifications
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
- D06M13/00—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment
- D06M13/322—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with compounds containing nitrogen
- D06M13/46—Compounds containing quaternary nitrogen atoms
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
- D06P5/00—Other features in dyeing or printing textiles, or dyeing leather, furs, or solid macromolecular substances in any form
- D06P5/02—After-treatment
- D06P5/04—After-treatment with organic compounds
- D06P5/06—After-treatment with organic compounds containing nitrogen
Definitions
- the invention relates to a process for removing oligomer deposits on textile materials which consist of polyester fibers or which contain these fibers in a mixture with other fibers, and from dyeing apparatus by treatment with aqueous, alkaline liquors at elevated temperatures.
- Polyester fibers contain oligomers, which often give rise to difficulties in processing and dyeing the polyester fibers.
- oligomers In the case of fibers made of linear polyesters made of terephthalic acid and glycol, it is primarily the cyclic trimere that causes disturbances in the processing or finishing of the polyester fibers.
- oligomers that are only very sparingly soluble in water are deposited in the dyeing device and also on the material to be colored. Some of the oligomers derived from the polyester remain in the liquor in fine distribution. The oligomer deposits on the polyester material often cause the levelness of the dyed material or the appearance of the goods to deteriorate.
- DE-A 28 34 413 discloses a process for the aftertreatment of textile material containing dyed polyester fiber, in which the textile material is treated with an aqueous emulsion of an oligomer-dissolving substance at a temperature below the glass transition point of the polyester fibers.
- Substances which are able to detach oligomers from the fiber are, for example, aliphatic or aromatic halogenated hydrocarbons or nonionic addition products of at most 10 mol alkylene oxide with 8 to 22 carbon atoms-containing alcohols, fatty acids or amines or with phenols optionally substituted by alkyl or phenyl, their Cloud points are below the application temperature. With this method, however, it is not possible to remove particularly firmly adhering oligomers from the polyester textile material.
- aqueous sodium hydroxide solution is optionally used in combination with solvents, such as trichlorobenzene or N-methylpyrrolidone, to remove oligomer deposits from dyeing apparatus.
- solvents such as trichlorobenzene or N-methylpyrrolidone
- the invention has for its object to design the method described in the introduction so that the oligomers are hydrolyzed as far as possible under gentler conditions than in the known methods, and therefore deposits do not remain on the textile material or in the apparatus, which could give rise to faults.
- the liquors contain emulsions of quaternary ammonium compounds which carry at least two C. to C 22 alkyl or alkenyl groups on the quaternary nitrogen atom, the quaternary ammonium compounds in an amount of 0.1 to 10 g / I are contained in the aqueous liquor and the weight ratio of the emulsifier to the quaternary ammonium compound is 0.1 to 2.
- Oligomers can be removed from textile material containing undyed polyester fibers as well as from dyed or optically brightened material and from dyeing machines.
- the method according to the invention is preferably applied to dyed textile materials which consist of polyester fibers or which contain these fibers in a mixture with other fibers and in which oligomers reach the fiber surface by heat treatment or have escaped from the fiber into the dyeing medium and result from it on the textile material or deposit in the dyeing machine.
- the oligomer deposits originate from the dye bath, and secondly the oligomers migrate from the inside to the surface of the polyester fibers under the dyeing conditions and thus cause problems during dyeing.
- the hydrolytic cleavage by the process according to the invention largely removes the oligomers deposited on the colored material and in the dyeing apparatus.
- Textile materials are to be understood as fibers that can be present in any processing stages, e.g. as cable, flake, sliver, staple fiber yarn, filament threads, knitwear, knitted fabric, woven or non-woven.
- the polyester fibers can also be blended with other fibers, e.g. Polyester and cotton, polyester and rayon, polyester and wool, polyester and synthetic polyamide fibers and polyester and polyacrylonitrile fibers.
- the polyester fibers are always dyed with disperse dyes and the other fibers in the case of fiber blends with the dyes of various classes suitable for these fibers, e.g. Cellulose fibers with vat or reactive dyes and under certain conditions also with disperse dyes, polyacrylonitrile fibers with basic dyes and polyamide fibers with disperse, anionic or metal complex dyes.
- the dyeing of the polyester fibers is carried out in accordance with the pull-out process, namely at temperatures in the range from 80 to 145 ° C. At temperatures above 100 ° C, pressure is used in the equipment known for dyeing.
- the usual dyeing accelerators can be used in the usual amounts, and other dyeing aids such as dispersants, wetting agents, lubricants and anti-foaming agents may be used.
- Diphenyl, chlorobenzenes, o-phenylphenol, reaction products of 1 mol of chlorophenol with 1 to 3 mol of ethylene oxide and salicylic acid esters are suitable as color accelerators.
- the pH of the liquor is usually set to between 4 and 6.
- the quaternary ammonium compounds in question are used in the liquor in an amount of 0.1 to 10 g / l, preferably 0.3 to 3 g / l. If the quaternary ammonium compounds are insoluble in water, they are used in emulsified form. Emulsification can be achieved, for example, by adding the quaternary ammonium compounds, dissolved in a monohydric alcohol, dimethylformamide, glycol, polyethylene glycol, glycerol, monomethylglycol ether, methyldiglycol or another polar solvent, with vigorous mixing of the aqueous aftertreatment liquor. Quaternary ammonium compounds containing alkylene oxide units are generally self-emulsifying.
- Cationic emulsifiers are e.g. alkoxylated fatty amines which are quaternized, for example reaction products of oleylamine and 6 to 10 mol of ethylene oxide which are completely quaternized with dimethyl sulfate or diethyl sulfate, or coconut fatty acid-y-dimethylaminopropylamide which is quaternized with epichlorohydrin.
- Suitable nonionic emulsifiers are, for example, ethoxylation products of fatty alcohols, C 1 -C 4 -alkyl phenols, fatty amines and fatty acids which are obtained by reacting the compounds mentioned with 5 to 50, preferably 15 to 45, moles of ethylene oxide.
- the fatty alcohols, fatty amines and fatty acids each have carbon numbers between 8 and 18.
- Castor oil which has been reacted with ethylene oxide is also suitable as a nonionic emulsifier, the molar ratio of castor oil: ethylene oxide being 1: 5 to 1:50.
- Stable emulsions of the quaternary ammonium compounds are obtained when the weight ratio of the emulsifier to the quaternary compound is 0.1 to 2. It is also possible to use mixtures of different emulsifiers, e.g. Mixtures of cationic and nonionic emulsifiers or of nonionic and anionic emulsifiers, provided that the use of the anionic emulsifiers does not lead to precipitation with the quaternary ammonium salts.
- this process can advantageously be carried out together with the usual reductive post-cleaning of textile material made of polyester.
- the textile material is treated with an aqueous alkaline liquor which contains a reducing agent, such as sodium dithionite, thiourea dioxide, sodium boranate or reductones, at temperatures between about 30 ° C. and the boiling point of the liquor.
- a reducing agent such as sodium dithionite, thiourea dioxide, sodium boranate or reductones
- the reverse order of the treatment stages is also possible, with the oligomers first being hydrolyzed and then the usual reductive post-cleaning carried out in the same bath or in a separate bath.
- the textile material or the dyeing apparatus is treated according to the invention at temperatures in the range between 30 and 100 ° C.
- the time required for the removal of the oligomers depends primarily on the temperature of the treatment liquor. Higher temperatures require shorter treatment times. They are between 1 minute and 24 hours.
- the temperature when removing the oligomers by the process according to the invention is preferably in the range from 70 to 90 ° C.
- the oligomers are removed with liquors containing quaternary ammonium salts, the pH of which is alkaline.
- the pH is in the range from 8 to 14 and is adjusted by adding bases such as sodium hydroxide solution or potassium hydroxide solution.
- the invention is illustrated by the following examples.
- the parts given in the examples are parts by weight, the data in percent relate to the weight of the substances, unless stated otherwise. Only the surface content of cyclic trimers is given in the examples. It was determined using the method of P. Kusch, Textilpraxis International 28, 96 to 98 (1973).
- the dyed yarn was then reductively cleaned in the dyeing apparatus with an aqueous liquor which contained 3 g / l of sodium dithionite, 5 ml / l of an aqueous sodium hydroxide solution at 38 ° Be and 0.5 g / l of an adduct of 45 moles of ethylene oxide and 1 mole of castor oil.
- the liquor ratio was 1: 20.
- the liquor flowed through the colored material from the inside to the outside.
- the reductive cleaning was carried out at a temperature of 70 ° C. and lasted 15 minutes.
- the fabric was rinsed with water at a temperature of 70 ° C and treated with dilute acetic acid for neutralization and then dried at a temperature of 100 ° C.
- the colored and reductively cleaned polyester material contained 0.2% of the cyclic trimers in the inner layers of the muff and 0.15% in the outer layers, in each case based on the fiber weight.
- the colored and reductively cleaned material was treated in the laboratory dyeing machine with a liquor containing 4 g / l of a mixture of 25% di- (iso-tridecyl) -dimethylammonium methosulfate, 25% of a reaction product, which was formed by the addition of 7 mol of ethylene oxide 1 mol of oleylamine and quaternization of the reaction product with dimethyl sulfate was obtained, 25% isopropanol and 25% water and 20 ml / l sodium hydroxide solution contained 38 ° Be.
- the liquor ratio was 1: 20.
- the liquor was heated to a temperature of 90 ° C. and acted on the colored and reductively cleaned material for 45 minutes.
- the material was then rinsed and acidified with dilute acetic acid and dried. Oligomers could not be detected either in the inner or in the outer layers of the cross wrap.
- a textured polyester yarn dyed according to Example 1 a) was treated for 45 minutes at a temperature of 90 ° C. with an aqueous liquor containing 3 g / l sodium dithionite, 20 ml / l sodium hydroxide solution 38 ° Be, 0.5 g / l of an adduct 45 moles of ethylene oxide in 1 mole of castor oil and 4 g / l of a mixture of tri- (iso-tridecyl) methylammonium methosulfate, 25% of the reaction product of 7 moles of ethylene oxide in 1 mole of oleylamine quaternized with dimethyl sulfate, 25% isopropanol and 25% Contained water. After rinsing, acidifying with dilute acetic acid and drying the material, no oligomers could be detected either in the inner or in the outer layers of the roll.
- the textured polyester yarn dyed according to Example 1 a) was aftertreated under the above conditions with an aqueous liquor containing only 3 g / l sodium dithionite, 20 ml / l sodium hydroxide solution 38 ° Be and 0.5 g / l of an adduct of Contained 45 moles of ethylene oxide in 1 mole of castor oil, the surface content of cyclic trimers after rinsing with water and acidifying with acetic acid was 0.15 in the inner layers and 0.1% in the outer layers.
- Example 1 a textured polyester yarn with 1.5%, based on the fiber weight, of the red disperse dye of C.I. No. 11 116 colored in a commercial setting.
- the colored material was treated with the liquor specified in Example 1 for the reductive post-cleaning for 15 minutes at a temperature of 80.degree. Thereafter, the oligomer content was 0.2% in the inner layers and 0.15% in the outer layers.
- a textured polyester yarn in the form of a muff was made with the red disperse dye from C.I. No. 11 116 colored in a commercial setting according to the details in Example 1 and then treated for 15 minutes with an aqueous liquor heated to 80 ° C., the 3 g / l sodium dithionite, 5 ml / l sodium hydroxide solution 38 ° Be, 0.5 g / I of the adduct of 45 moles of ethylene oxide with 1 mole of castor oil and 4 g / I of a mixture of 25% tri- (iso-decyl) methylammonium methosulfate, 25% coconut fatty acid-y-dimethylaminopropylamide, quaternized with epichlorohydrin and 50% isopropanol.
- the liquor ratio was 1: 20. After rinsing and acidifying with dilute acetic acid, the surface content of cyclic trimers was 0.03%.
- 1.1 kg of a textured polyester yarn in Form of a muff was colored within 60 minutes at a temperature of 130 ° C with an aqueous liquor containing 3% of the red disperse dye of CI No. 60 756 in a commercial setting, 0.5 g / I of the sodium salt of a condensation product of naphthalene sulfonic acid and Formaldehyde, 0.5 ml / l 30% aqueous acetic acid and 0.5 g / l sodium salt of ethylenediaminetetraacetic acid contained.
- the liquor ratio was 1:20, the liquor flowed through the material from the inside out.
- the textured polyester yarn was reductively cleaned by treating it for 20 minutes at a temperature of 80 ° C. with an aqueous liquor containing 10 ml / l sodium hydroxide solution 38 ° C, 3 g / l sodium dithionite and 0.5 g / l of an adduct of 45 moles of ethylene oxide with 1 mole of castor oil.
- the liquor ratio was 1:20, the liquor flowed through the material from the inside out.
- the dyed and reductively cleaned yarn was treated for 20 minutes with a liquor heated to 80 ° C., the 10 ml / l sodium hydroxide solution 38 ° Bè and 4 g / l of a mixture of 25% tri- (n-octyl ) -methylammonium chloride, 25% coconut fatty acid-y-dimethylaminopropylamide, quaternized with benzyl chloride, and 50% isopropanol contained.
- the liquor ratio was 1: 20. Thereafter, only traces (less than 0.01%) of oligomers were present on the yarn surface.
- a textured polyester yarn which was in the form of a muff, was dyed according to the instructions given in Example 4 a) and then subjected to the reductive post-cleaning, the conditions specified in Example 4 a) for the reductive post-cleaning being selected and the liquor additionally 4 g / l of a mixture of 25% tri- (n-octyl) methylammonium chloride, 25% coconut fatty acid-y-dimethylamino-propylamide, quaternized with benzyl chloride, and 50% isopropanol. After rinsing and drying the post-treated polyester material, only traces ( ⁇ 0.01%) of the cyclic trimers were detectable on the fiber surface.
- polyester sliver 600 g were dyed in a packing cylinder with a liquor of the following composition: 1%, based on the material to be dyed, of the blue disperse dye from C.I. No. 63 285 in a commercial setting, 0.5 g / l of the sodium salt of a condensation product of naphthalenesulfonic acid and formaldehyde and 0.5 ml / l of 30% aqueous acetic acid. The liquor ratio was 1:30.
- the dyeing was carried out at a temperature of 130 ° C. and was complete after 60 minutes at this temperature.
- the liquor was discharged at a temperature of 80 ° C.
- the material to be dyed was then rinsed twice with water at a temperature of 80 ° C.
- the dyed and reductively cleaned fiber material was treated in apparatus to remove the oligomers with an aqueous liquor containing 8 g / l of a mixture of 25% di- (isodecyl) dimethylammonium methosulfate, 25% of the adduct of 7 moles of ethylene oxide and oleylamine, quaternized with dimethyl sulfate, 25% isopropanol and 25% water and 15 ml / l sodium hydroxide solution contained 38 ° Bè.
- the liquor ratio was 1: 30. After the liquor had acted on the textile for 30 minutes at a temperature of 80 ° C., no more cyclic trimers could be detected on the fiber surface after rinsing the textile with water.
- a polyester sliver dyed according to Example 5 a) was treated for 30 minutes at a temperature of 80 ° C. with an aqueous liquor containing 15 ml / l sodium hydroxide solution 38 ° Be, 3 g / l sodium dithionite, 0.5 g / l of the adduct 45 mol of ethylene oxide in 1 mol of castor oil and 8 g / l of a mixture of 25% di- (isodecyl) dimethylammonium methosulfate, 25% of the adduct of 7 mol of ethylene oxide and 1 mol of oleylamine, quaternized with dimethyl sulfate, 25% isopropanol and 25 % Water contained.
- the liquor ratio was 1: 30. After rinsing and drying the polyester sliver, the surface content was found to be 0.02% cyclic trimers.
- Two 20 g sections of a textured polyester knit cleaned with perchlorethylene Goods were dyed in a multicolor printing dyeing machine (from Pretema) as follows: 1 g of the dye of the formula in commercial form were dispersed in 300 ml of deionized water. In addition, 3 g / l of a mixture of di- and trichlorobenzene (carrier) and 0.5 g / l of the sodium salt of a condensation product of naphthalenesulfonic acid and formaldehyde were added and the pH was adjusted to 4.5 with acetic acid. The mixture was heated to 130 ° C. in 30 minutes and stained at 130 ° C. for 60 minutes.
- Untreated polyester knitted fabrics were dyed with 1% of the dye of CI No. 11 116 in a commercially available form, as described in Example 6, with the only difference that 2 g / l of the mixture of di- and trichlorobenzene were used. After cooling to 80 ° C., 4 ml / l sodium hydroxide solution 38 ° Be, 2 g / l sodium dithionite and 0.5 g / l of an adduct of 45 mol ethylene oxide and 1 mol castor oil were added and the mixture was reductively cleaned at 80 ° C. for 20 minutes. After the liquor had been drained and the goods had been rinsed once hot, they were treated for 30 minutes at 80 ° C.
- Coloring and aftertreatment were carried out as described in Example 7, but 9 g / l of an active ingredient mixture of 22 parts of tri (nC 6/10 alkyl) methylammonium methosulfate, 22 parts of the adduct of 7 mol of ethylene oxide and 1 mol Oleylamine quaternized with dimethyl sulfate, 22 parts isopropanol and 34 parts water.
- the cyclic trimers content on the innermost roll was 0.05%.
- a liquor was alternately circulated in both directions at a temperature of 95 ° C. for 30 minutes, the 20 ml / l sodium hydroxide solution 38 ° Bè, 8 g / l sodium dithionite, 8 g / l of a mixture of 25% tri (n-octyl) methylammonium methosulfate, 25% of the adduct of 7 moles of ethylene oxide with 1 mole of oleylamine, quaternized with dimethyl sulfate, 25% isopropanol and 25% water and 2 g / l of Addition product of 12 moles of ethylene oxide to 1 mole of oleylamine contained. Then it was rinsed several times with water. The apparatus was then free of the deposits mentioned above.
Landscapes
- Engineering & Computer Science (AREA)
- Textile Engineering (AREA)
- Coloring (AREA)
- Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
- Laminated Bodies (AREA)
- Treatments Of Macromolecular Shaped Articles (AREA)
- Detergent Compositions (AREA)
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
AT80102715T ATE2967T1 (de) | 1979-06-23 | 1980-05-16 | Verfahren zum entfernen von oligomerenablagerungen auf textilen materialien. |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE2925477 | 1979-06-23 | ||
DE19792925477 DE2925477A1 (de) | 1979-06-23 | 1979-06-23 | Verfahren zum entfernen von oligomerenablagerungen auf textilen materialien |
Publications (2)
Publication Number | Publication Date |
---|---|
EP0021011A1 EP0021011A1 (de) | 1981-01-07 |
EP0021011B1 true EP0021011B1 (de) | 1983-04-06 |
Family
ID=6074029
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
EP80102715A Expired EP0021011B1 (de) | 1979-06-23 | 1980-05-16 | Verfahren zum Entfernen von Oligomerenablagerungen auf textilen Materialien |
Country Status (7)
Country | Link |
---|---|
US (1) | US4294576A (ja) |
EP (1) | EP0021011B1 (ja) |
JP (1) | JPS5649091A (ja) |
AT (1) | ATE2967T1 (ja) |
DE (2) | DE2925477A1 (ja) |
ES (1) | ES8103225A1 (ja) |
PT (1) | PT71396A (ja) |
Families Citing this family (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE3605716A1 (de) * | 1986-02-22 | 1987-09-03 | Henkel Kgaa | Verwendung von unloeslichen schmutzsammlern zur regenerierung von wasch- und reinigungsloesungen |
JPH088819B2 (ja) * | 1988-04-20 | 1996-01-31 | 山口育苗合名会社 | 育苗方法 |
CN1112449C (zh) * | 1996-03-06 | 2003-06-25 | 加利福尼亚大学董事会 | 酶处理以增强纺织物的润湿性和吸收性 |
US5711764A (en) * | 1996-10-03 | 1998-01-27 | Wasinger; Eric M. | Composition and process for decolorizing and/or desizing garments |
US6844307B1 (en) | 2002-02-04 | 2005-01-18 | Jeffrey Todd Sumner | Compositions to reduce textile contaminants and associated processing methods |
SI21189A (sl) * | 2002-03-25 | 2003-10-31 | Univerza V Ljubljani, | Metoda predobdelave poliestra za znižanje izločanja oligomerov pri visokotemperaturnem kislem barvanju z disperzijskimi barvili |
US6911421B2 (en) * | 2002-11-01 | 2005-06-28 | Nicca Usa, Inc. | Surfactant blends for removing oligomer deposits from polyester fibers and polyester processing equipment |
CN111945444A (zh) * | 2020-07-24 | 2020-11-17 | 江苏海云花新材料有限公司 | 涤纶高温染色低聚物去除剂 |
Family Cites Families (11)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2587597A (en) * | 1949-07-14 | 1952-03-04 | Arkansas Company Inc | Process for removal of pigments from printed textiles and agents useful therein |
NL189533C (nl) * | 1953-07-29 | Ates Componenti Elettron | Werkwijze voor het aanbrengen van een kunststofhouder met warmte-afvoer rond een geintegreerde schakeling, alsmede combinatie van een matrijs en een warmte-afvoerelement voor gebruik bij deze werkwijze. | |
NL259354A (ja) * | 1959-12-22 | |||
US3684431A (en) * | 1969-01-10 | 1972-08-15 | Ciba Geigy Ag | Process for after-washing freshly dyed textile material |
DE2220710A1 (de) * | 1972-04-27 | 1973-11-08 | Bayer Ag | Nassechtheitsverbesserungsmittel |
US3816321A (en) * | 1972-05-03 | 1974-06-11 | Procter & Gamble | Laundering aid |
JPS5059592A (ja) * | 1973-10-01 | 1975-05-22 | ||
DE2508245C2 (de) * | 1975-02-26 | 1977-04-07 | Bayer Ag | Verfahren zur nachbehandlung von gefaerbten textilmaterialien |
DE2641608C3 (de) * | 1976-09-16 | 1981-06-25 | Öffentliche Prüfstelle und Textilinstitut für Vertragsforschung e.V., 4150 Krefeld | Verfahren zum Färben von textilen Materialien unter Vorschaltung einer Vorreinigung |
GB1587122A (en) * | 1976-10-29 | 1981-04-01 | Procter & Gamble Ltd | Fabric conditioning compositions |
CH611107B (de) * | 1977-08-25 | Ciba Geigy Ag | Verfahren zur entfernung von oligomeren-ausscheidungen aus gefaerbtem, polyesterfasern enthaltendem textilmaterial. |
-
1979
- 1979-06-23 DE DE19792925477 patent/DE2925477A1/de not_active Withdrawn
-
1980
- 1980-05-16 AT AT80102715T patent/ATE2967T1/de not_active IP Right Cessation
- 1980-05-16 EP EP80102715A patent/EP0021011B1/de not_active Expired
- 1980-05-16 DE DE8080102715T patent/DE3062596D1/de not_active Expired
- 1980-05-22 US US06/152,178 patent/US4294576A/en not_active Expired - Lifetime
- 1980-06-12 PT PT71396A patent/PT71396A/pt unknown
- 1980-06-23 ES ES492695A patent/ES8103225A1/es not_active Expired
- 1980-06-23 JP JP8411780A patent/JPS5649091A/ja active Pending
Also Published As
Publication number | Publication date |
---|---|
JPS5649091A (en) | 1981-05-02 |
ES492695A0 (es) | 1981-02-16 |
ATE2967T1 (de) | 1983-04-15 |
DE2925477A1 (de) | 1981-01-22 |
DE3062596D1 (en) | 1983-05-11 |
US4294576A (en) | 1981-10-13 |
EP0021011A1 (de) | 1981-01-07 |
ES8103225A1 (es) | 1981-02-16 |
PT71396A (de) | 1980-07-01 |
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PUAI | Public reference made under article 153(3) epc to a published international application that has entered the european phase |
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AK | Designated contracting states |
Designated state(s): AT BE CH DE FR GB IT NL SE |
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17P | Request for examination filed |
Effective date: 19810401 |
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