EP0011814B1 - Process for dyeing mixtures of polyester and wool - Google Patents
Process for dyeing mixtures of polyester and wool Download PDFInfo
- Publication number
- EP0011814B1 EP0011814B1 EP79104617A EP79104617A EP0011814B1 EP 0011814 B1 EP0011814 B1 EP 0011814B1 EP 79104617 A EP79104617 A EP 79104617A EP 79104617 A EP79104617 A EP 79104617A EP 0011814 B1 EP0011814 B1 EP 0011814B1
- Authority
- EP
- European Patent Office
- Prior art keywords
- polyester
- dyeing
- wool
- alkyl
- carriers
- 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
- D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
- D06P1/00—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed
- D06P1/44—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed using insoluble pigments or auxiliary substances, e.g. binders
- D06P1/64—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed using insoluble pigments or auxiliary substances, e.g. binders using compositions containing low-molecular-weight organic compounds without sulfate or sulfonate groups
- D06P1/651—Compounds without nitrogen
- D06P1/6515—Hydrocarbons
- D06P1/65156—Halogen-containing hydrocarbons
Definitions
- the required amounts of the chlorinated alkylbenzenes of the formula (I) to be used according to the invention can easily be determined from case to case by preliminary search. In general, amounts of 1 to 7 g per liter of dyeing liquor have proven themselves in the usual liquor ratios of 1: 5 to 1:40, or 10 to 40 g per liter of padding liquor.
- chlorinated alkyl benzenes to be used according to the invention are well compatible with other carriers, they can also be used in a mixture with known other carriers.
- the chlorinated alkyl benzenes of the formula (I) to be used according to the invention are advantageously used together with anionic or nonionic emulsifiers or dispersants.
- the disperse dyes used in the dyeing process according to the invention are the disperse dyes usually used for dyeing polyesters and cellulose esters, as described, for example, in "Color Index” Vol. 2, pp. 2483-2741, 3rd edition (1971).
- the dyeing of the structures consisting of polyesters or cellulose esters and wool in the presence of the chlorinated alkylbenzenes to be used according to the invention is carried out by customary continuous or batch processes; The following may be mentioned as such: the customary process operating at 98 ° C., the high temperature and the thermosol process.
- the isomer mixtures such as those obtained in the industrial chlorination of toluene, have been found to be particularly suitable.
- Threads, fibers, fabrics, knitted fabrics, films and foils made of polyesters, such as polyterephthalic acid glycol esters, or polyesters made of 1,4-bis (hydroxymethyl) cyclohexane and terephthalic acid, and cellulose esters, e.g. Cellulose triacetate, with disperse dyes in deep shades and excellent to dye evenly.
- polyesters such as polyterephthalic acid glycol esters, or polyesters made of 1,4-bis (hydroxymethyl) cyclohexane and terephthalic acid
- cellulose esters e.g. Cellulose triacetate
- Disperse dyes such as halobenzenes, alkyl phthalimides, aromatic carboxylic acid esters, methyl and methoxynaphthalenes, diphenyl, diphenyl ether, o-, m-up-oxydiphenyls or p-oxydiphenyl ethers.
- halobenzenes alkyl phthalimides
- aromatic carboxylic acid esters methyl and methoxynaphthalenes
- diphenyl diphenyl ether
- o-, m-up-oxydiphenyls or p-oxydiphenyl ethers o-, m-up-oxydiphenyls or p-oxydiphenyl ethers.
- Diphenyl has good carrier properties, but it has the disadvantage of causing stains on the textiles because, due to its high melting point, it easily crystallizes out in the dyebaths and emulsifies poorly when the baths are heated.
- Diphenyl ether has the disadvantage that its carrier activity depends strongly on the constitution of the disperse dye used, and therefore when dyeing with dye combinations, e.g. those for the production of gray and olive tones, no reproducible colorations can be obtained.
- p-oxy-diphenyl has good carrier properties, it cannot be used as a carrier in the normal dyeing process at 98-100 ° C, since it is still solid at these temperatures. It also affects the lightfastness of the dyeings.
- chlorinated alkylbenzenes to be used according to the invention have the advantages over these carriers mentioned. that they do not cause stains, that they do not adversely affect the lightfastness of the dyeings, that their effectiveness is independent of the dye constitution, that they can therefore be used to produce reproducible combination dyeings and that the odor nuisance is low.
- the chlorinated alkyl benzenes have the advantage that they are effective even in lower concentrations. It should also be emphasized that they at least do not impair the build-up capacity of the disperse dyes, if not improve them, as do other carriers which retain the dyes in the dyebath. Another advantage is the excellent compensation for thread structure differences of heat-set polyester material.
- a combination with 1,2,4-trichlorobenzene has proven to be particularly advantageous. While a pure trichlorobenzene setting already crystallizes at + 10 ° C to + 17 ° C, suitable combinations with dichlorotoluene result in freezing points down to - 20 ° C.
- the compounds (I) to be used according to the invention are superior in terms of constitution to the closest chlorobenzene even that the wool portion is less soiled when dyeing the polyester portion of polyester-wool blended materials.
Description
Die Verwendung von Mono- oder Polychlorderivaten der Mono- oder Dialkylbenzolreihe, beispielsweise Mono- und Di-chlortoluol und Monochlor-zylol als Carrier beim Färben von Polyestermaterialien ist beispielsweise aus der DE - B - 1 199 732, der NL - A 6 809 649 und der US - A - 3 644 080 bekannt. In diesen Veröffentlichungen wird jedoch nicht erwähnt, daß die Verbindungen auch dann vorteilhaft als Carrier verwendet werden können, wenn Polyester in Gegenwart von Wolle gefärbt wird. Der Einfluß der Verbindungen auf Wolle, die bei dem Färbe-prozeß möglichst wenig angeschmutzt werden sollte, war demnach bisher nicht bekannt.The use of mono- or polychloro derivatives of the mono- or dialkylbenzene series, for example mono- and di-chlorotoluene and monochlorocylene as carriers in the dyeing of polyester materials, is known for example from DE-B-1 199 732, NL-A 6 809 649 and the US - A - 3 644 080 known. However, it is not mentioned in these publications that the compounds can also advantageously be used as carriers if polyester is dyed in the presence of wool. The influence of the compounds on wool, which should be soiled as little as possible in the dyeing process, has therefore not been known to date.
Es wurde nun ein Verfahren zum Färben des Polyesteranteils von Polyester-Wolle-Mischmaterialien mit Dispersionsfarbstoffen gefunden. Das Verfahren ist dadurch gekennzeichnet, daß man das Färben oder Bedrucken in Gegenwart von chlorierten Alkylbenzolen der allgemeinen Formel
- n = 1-3
- R = H, Alkyl mit 1-4 Kohlenstoffatomen
- vornimmt.
- n = 1-3
- R = H, alkyl of 1-4 carbon atoms
- makes.
Die erforderlichen Mengen der erfindungsgemäß zu verwendenden chlorierten Alkylbenzole der Formel (I) lassen sich durch Vorwersuche von Fall zu Fall leicht ermitteln. Im allgemeinen haben sich Mengen von 1 bis 7 g je Liter Färbeflotte bei den üblichen Flottenverhältnissen von 1:5 - 1:40, bzw. 10 bis 40 g je Liter Klotzflotte, bewährt.The required amounts of the chlorinated alkylbenzenes of the formula (I) to be used according to the invention can easily be determined from case to case by preliminary search. In general, amounts of 1 to 7 g per liter of dyeing liquor have proven themselves in the usual liquor ratios of 1: 5 to 1:40, or 10 to 40 g per liter of padding liquor.
Da die erfindungsgemäß zu verwendenden chlorierten Alkyl-benzole gut verträglich mit anderen Carriern sind, können sie auch in Mischung mit bekannten anderen Carriern verwendet werden.Since the chlorinated alkyl benzenes to be used according to the invention are well compatible with other carriers, they can also be used in a mixture with known other carriers.
Die erfindungsgemäß zu verwendenden chlorierten Alkyl-benzole der Formel (I) werden vorteilhaft zusammen mit anionaktiven oder nichtionogenen Emulgiermitteln bzw. Dispergiermitteln eingesetzt. Besonders bewährt haben sich als Emulgatoren Gemische aus a) oxäthylierten Ölen, wie Rizinusöl oder Sojaöl, oxäthylierten Alkoholen, Alkylphenolpolyglykoläthern oder Phenylalkylphenolpolyglykoläthern, b) Alkali, Erdalkali- und/oder Ammoniumsalzen organischer mindestens 10 Kohlenstoffatome aufweisender Sulfonsäuren, wie Didecylbenzolsulfonsäure, Diisobutylnaphthalinsulfonsäure, a-Sulfofettsäuren und Rizinoleyl-methyltaurid. Die Mengen an Emulgier- bzw. Dispergiermitteln betragen zweck-mäßig 5 bis 15 % des Gewichts der Carriereinstellung.The chlorinated alkyl benzenes of the formula (I) to be used according to the invention are advantageously used together with anionic or nonionic emulsifiers or dispersants. Mixtures of a) oxyethylated oils, such as castor oil or soybean oil, oxyethylated alcohols, alkylphenol polyglycol ethers or phenylalkylphenol polyglycol ethers, b) alkali, alkaline earth metal and / or ammonium salts of organic sulfonic acids having at least 10 carbon atoms, such as didecyl sulfonylsulfonyl sulfonyl sulfonylsulfonyl sulfonylsulfonic acid, such as didecyl sulfonyl sulfonyl sulfonylsulfonyl sulfonylsulfonate, and ricinoleyl methyl tauride. The amounts of emulsifiers or dispersants are expediently 5 to 15% of the weight of the carrier setting.
Die bei dem erfindungsgemäßen Färbeverfahren zur Anwendung gelangenden Dispersionsfarbstoffe sind die üblicherweise zum Färben von Polyestern und Celluloseestern verwendeten Dispersionsfarbstoffe, wie sie beispielsweise in "Colour Index" Vol. 2, S. 2483-2741, 3. Edition (1971) beschreiben sind. Das Färben der aus Polyestern oder Celluloseestern und Wolle bestehenden Gebilde in Gegenwart der erfindungsgemäß zu verwendenden chlorierten Alkylbenzole wird nach üblichen kontinuierlichen oder diskontinuierlichen Verfahren durchgeführt; als solche seien genannt: das übliche bei 98°C arbeitende Verfahren, das Hochtemperatur- und das Thermosol-Verfahren.The disperse dyes used in the dyeing process according to the invention are the disperse dyes usually used for dyeing polyesters and cellulose esters, as described, for example, in "Color Index" Vol. 2, pp. 2483-2741, 3rd edition (1971). The dyeing of the structures consisting of polyesters or cellulose esters and wool in the presence of the chlorinated alkylbenzenes to be used according to the invention is carried out by customary continuous or batch processes; The following may be mentioned as such: the customary process operating at 98 ° C., the high temperature and the thermosol process.
Als Vertreter der erfindungsgemäß zu verwendenden Verbindungen der Formel (I) seien beispielsweise genannt: Die isomeren Mono-, Di- und Trichlorotoluole, 4-Chlor-1,3-di-methylbenzol, 2-Chlor-1,4-dimethylbenzol und 2,5-Dichlor-1,4-dimethylbenzol.The following are examples of the compounds of the formula (I) to be used according to the invention: the isomeric mono-, di- and trichlorotoluenes, 4-chloro-1,3-dimethylbenzene, 2-chloro-1,4-dimethylbenzene and 2, 5-dichloro-1,4-dimethylbenzene.
Als besonders vorteilhaft bei dem erfindungsgemäßen Verfahren erwiesen sich Dichlortoluole der allgemeinen FormelDichlorotoluenes of the general formula have proven to be particularly advantageous in the process according to the invention
Insbesondere die Isomerengemische, wie sie bei der technischen Chlorierung von Toluol anfallen, haben sich als besonders geeignet herausgestellt.In particular, the isomer mixtures, such as those obtained in the industrial chlorination of toluene, have been found to be particularly suitable.
Mit Hilfe des erfindungsgemäßen Verfahrens gelingt es, Gebilde, z.B. Fäden, Fasern, Gewebe, Gewirke, Filme und Folien aus Polyestern, wie Polyterephthalsäureglykolestern, oder Polyestern aus 1,4-Bis-(hydroxymethyl)-cyclohexan und Terephthalsäure, und Celluloseestern, z.B. Cellulosetriacetat, mit Dispersionsfarbstoffen in tiefen Tönen und hervorragend gleichmäßig zu färben.With the help of the method according to the invention, it is possible to construct e.g. Threads, fibers, fabrics, knitted fabrics, films and foils made of polyesters, such as polyterephthalic acid glycol esters, or polyesters made of 1,4-bis (hydroxymethyl) cyclohexane and terephthalic acid, and cellulose esters, e.g. Cellulose triacetate, with disperse dyes in deep shades and excellent to dye evenly.
Es sind schon viele Verbindungen als Carrier zum Färben von Polyester-Materialien mit Dispersionsfarbstoffen vorgeschlagen worden, wie Halogenbenzole, Alkylphthalimide, aromatische Carbonsäureester, Methyl- und Methoxynaphthaline, Diphenyl, Diphenyläther, o-, m- u.p-Oxydiphenyle oder p-Oxydiphenyläther. Diese Verbindungen haben jedoch Nachteile.There are already many compounds as carriers for dyeing polyester materials Disperse dyes have been proposed, such as halobenzenes, alkyl phthalimides, aromatic carboxylic acid esters, methyl and methoxynaphthalenes, diphenyl, diphenyl ether, o-, m-up-oxydiphenyls or p-oxydiphenyl ethers. However, these connections have disadvantages.
Alle Verbindungen, bis auf die Alkylphthalimide, sind stark geruchsbelästigend, Mono- und Dichlorbenzole sind stark lebertoxisch, während die Methyl- und Methoxynaphthaline den Nachteil haben, daß sie die Lichtechtheit der Färbungen nachteilig beeinflussen. Diphenyl besitzt zwar gute Carriereigenschaften, hat aber den Nachteil, Flecken auf den Textilien zu verursachen, weil es wegen seines hohen Schmelzpunktes in den Färbebädern leicht auskristallisiert und beim Anheizen der Bäder schlecht emulgiert. Diphenyläther hat den Nachteil, daß seine Carrierwirksamkeit stark von der Konstitution des verwendeten Dispersionsfarbstoffs abhängt, und daß deshalb beim Färben mit Farbstoffkombinationen, z.B. solchen zur Erzeugung von Grau- und Olivtönen, keine reproduzierbaren Färbungen erhalten werden. p-Oxy-diphenyl besitzt zwar gute Carriereigenschaften, kann aber nicht als Carrier im Normalfärbeverfahren bei 98-100°C eingesetzt werden, da es bei diesen Temperaturen noch fest ist. Außerdem beeinträchtigt es die Lichtechtheit der Färbungen.All compounds, with the exception of the alkyl phthalimides, are highly odor-causing, mono- and dichlorobenzenes are highly toxic to the liver, while the methyl- and methoxynaphthalenes have the disadvantage that they adversely affect the lightfastness of the dyeings. Diphenyl has good carrier properties, but it has the disadvantage of causing stains on the textiles because, due to its high melting point, it easily crystallizes out in the dyebaths and emulsifies poorly when the baths are heated. Diphenyl ether has the disadvantage that its carrier activity depends strongly on the constitution of the disperse dye used, and therefore when dyeing with dye combinations, e.g. those for the production of gray and olive tones, no reproducible colorations can be obtained. Although p-oxy-diphenyl has good carrier properties, it cannot be used as a carrier in the normal dyeing process at 98-100 ° C, since it is still solid at these temperatures. It also affects the lightfastness of the dyeings.
Gegenüber diesen genannten Carriern weisen die erfindungsgemäß zu verwendenden chlorierten Alkylbenzole die Vorteile auf. daß sie keine Flecken verursachen, daß sie die Lichtechtheit der Färbungen nicht nachteilig beeinflussen, daß ihre Wirksamkeit unabhängig von der Farbstoffkonstitution ist, daß sich deshalb mit ihrer Hilfe reproduzierbare Kombinationsfärbungen herstellen lassen und daß die Geruchbelästigung gering ist.The chlorinated alkylbenzenes to be used according to the invention have the advantages over these carriers mentioned. that they do not cause stains, that they do not adversely affect the lightfastness of the dyeings, that their effectiveness is independent of the dye constitution, that they can therefore be used to produce reproducible combination dyeings and that the odor nuisance is low.
Gegenüber den erwähnten Alkylnaphthalimiden weisen die chlorierten Alkylbenzole den Vorteil auf, daß sie bereits in geringeren Konzentrationen wirksam sind. Außerdem sei hervorgehoben, daß sie das Aufbauvermögen der Dispersionsfarbstoffe wenn nicht gar verbessern zumindest aber nicht beeinträchtigen wie dies andere Carrier bewirken, die die Farbstoffe im Färbebad zurückhalten. Als weiterer Vorteil sei das ausgezeichnete Ausgleichsvermögen für Fadenstrukturdifferenzen von thermofixiertem Polyester-Material gennant.Compared to the alkyl naphthalimides mentioned, the chlorinated alkyl benzenes have the advantage that they are effective even in lower concentrations. It should also be emphasized that they at least do not impair the build-up capacity of the disperse dyes, if not improve them, as do other carriers which retain the dyes in the dyebath. Another advantage is the excellent compensation for thread structure differences of heat-set polyester material.
Als besonders vorteilhaft hat sich eine Kombination mit 1,2,4-Trichlorbenzol erwiesen. Während eine reine Trichlorbenzol-Einstellung bereits bei + 10° C bis + 17° C auskristallisiert, ergeben geeignete Kombinationen mit Dichlortoluol Erstarrungspunkte bis zu - 20° C.A combination with 1,2,4-trichlorobenzene has proven to be particularly advantageous. While a pure trichlorobenzene setting already crystallizes at + 10 ° C to + 17 ° C, suitable combinations with dichlorotoluene result in freezing points down to - 20 ° C.
Überraschenderweise wurde gefunden, daß die erfindungsgemäß zu verwendenden Verbindungen (I) dem konstitutionsmäßig nächstliegenden Chlorbenzol sogar dann überlegen sind, daß in ihrer Gegenwart beim Färben des Polyester-Anteils von Polyester-Wolle-Mischmaterialien der Wollanteil weniger angeschmutzt wird.Surprisingly, it was found that the compounds (I) to be used according to the invention are superior in terms of constitution to the closest chlorobenzene even that the wool portion is less soiled when dyeing the polyester portion of polyester-wool blended materials.
Claims (1)
- Process for dyeing the polyester part of polyester/wool mixed materials with dispersion dyestuffs, characterised in that dyeing is carried out in the presence of chlorinated alkylbenzenes of the general formula
n = 1-3R = H or alkyl with 1 to 4 carbon atoms.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2852027 | 1978-12-01 | ||
| DE19782852027 DE2852027A1 (en) | 1978-12-01 | 1978-12-01 | METHOD FOR COLORING POLYESTER-CONTAINING MATERIALS |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| EP0011814A1 EP0011814A1 (en) | 1980-06-11 |
| EP0011814B1 true EP0011814B1 (en) | 1983-02-16 |
Family
ID=6056083
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| EP79104617A Expired EP0011814B1 (en) | 1978-12-01 | 1979-11-21 | Process for dyeing mixtures of polyester and wool |
Country Status (5)
| Country | Link |
|---|---|
| US (1) | US4279614A (en) |
| EP (1) | EP0011814B1 (en) |
| JP (1) | JPS5580585A (en) |
| BR (1) | BR7907800A (en) |
| DE (2) | DE2852027A1 (en) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA1307482C (en) * | 1987-11-09 | 1992-09-15 | Ronald G. Schoner | Vectors and expression sequences for production of polypeptides |
| US5112292A (en) * | 1989-01-09 | 1992-05-12 | American Biomed, Inc. | Helifoil pump |
Family Cites Families (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR1069902A (en) * | 1953-01-16 | 1954-07-13 | Hoechst Ag | Process for dyeing articles obtained from polyvinyl chloride or copolymers derived from vinyl chloride and articles thus dyed |
| DE1199732B (en) * | 1957-01-05 | 1965-09-02 | Kuhlmann Ets | Process for dyeing or printing polyester fibers |
| DE1918340A1 (en) * | 1968-04-10 | 1969-10-23 | Ici Ltd | Coloring process |
| NL6809649A (en) * | 1968-07-09 | 1968-11-25 | ||
| US3644079A (en) * | 1969-07-11 | 1972-02-22 | Collins & Aikman Corp | Method for improving the dyeability and for heat setting synthetic linear polyesters |
| US3650663A (en) * | 1969-09-15 | 1972-03-21 | Collins & Aikman Corp | Method for treating synthetic linear polyesters fibers and film in the vapor phase to improve the dyeability and to heat set said polyesters |
| US3644080A (en) * | 1969-09-15 | 1972-02-22 | Collins & Aikman Co | Method of printing synthetic linear polyester sheet materials |
| US3992143A (en) * | 1971-03-23 | 1976-11-16 | Bayer Aktiengesellschaft | Exhaust process for the dyeing of synthetic fiber materials |
| NL7204838A (en) * | 1971-04-14 | 1972-10-17 | ||
| US3894842A (en) * | 1972-03-10 | 1975-07-15 | Hoechst Ag | Process for preparing dyeings and prints fast to light on synthetic fibers |
| US4018558A (en) * | 1973-05-09 | 1977-04-19 | Ciba-Geigy Corporation | Exhaust process for the dyeing of synthetic organic textile material in navy blue to black shades |
| US4013408A (en) * | 1973-05-09 | 1977-03-22 | Ciba-Geigy Corporation | Exhaust process for the dyeing of synthetic organic textile materials in navy blue to black shades |
-
1978
- 1978-12-01 DE DE19782852027 patent/DE2852027A1/en not_active Withdrawn
-
1979
- 1979-11-14 US US06/093,951 patent/US4279614A/en not_active Expired - Lifetime
- 1979-11-21 DE DE7979104617T patent/DE2964858D1/en not_active Expired
- 1979-11-21 EP EP79104617A patent/EP0011814B1/en not_active Expired
- 1979-11-29 JP JP15495479A patent/JPS5580585A/en active Pending
- 1979-11-30 BR BR7907800A patent/BR7907800A/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| JPS5580585A (en) | 1980-06-17 |
| US4279614A (en) | 1981-07-21 |
| BR7907800A (en) | 1980-06-24 |
| DE2852027A1 (en) | 1980-06-12 |
| EP0011814A1 (en) | 1980-06-11 |
| DE2964858D1 (en) | 1983-03-24 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE1290915B (en) | Process for dyeing and printing fiber materials made from aromatic polyesters and cellulose acetates | |
| EP0491764A1 (en) | Benzophenone ether esters, process for making them and their use in improving the light-stability of polyester dyes. | |
| DE2721084A1 (en) | MIXTURES OF OPTICAL BRIGHTENERS | |
| DE2602750A1 (en) | ORGANIC COMPOUNDS, THEIR PRODUCTION AND USE | |
| EP0310973B1 (en) | Levelling agent | |
| EP0011814B1 (en) | Process for dyeing mixtures of polyester and wool | |
| EP0212562B1 (en) | Process for dyeing fine titer polyester fibres | |
| DE1963735C3 (en) | Monoazo dyes and processes for the continuous dyeing of synthetic fiber materials | |
| DE2755295C3 (en) | Process for dyeing polyester materials | |
| EP0414631A1 (en) | Auxiliary agent mixture and its use in dyeing polyester fibre materials | |
| DE2252123A1 (en) | PROCESS FOR COLORING SYNTHETIC FIBER MATERIALS FROM ORGANIC SOLVENTS | |
| DE3247400C2 (en) | ||
| DE1644209C3 (en) | Monoazo dyes, process for their preparation and their use | |
| DE2502234A1 (en) | PREPARATION AND PROCESS FOR CURVE-FREE COLORING OF POLYESTER FIBERS | |
| DE1941699A1 (en) | Process for the continuous dyeing of synthetic fiber materials | |
| DE1619497A1 (en) | Process for dyeing structures made of aromatic polyesters or cellulose triacetate | |
| DE2236551C3 (en) | Carrier mixture and process for dyeing and printing | |
| DE2422333A1 (en) | COLORING PROCESS | |
| EP0811041A1 (en) | Method of dyeing polyester and polyester-containing textile materials | |
| DE2348363A1 (en) | CARRIER PREPARATION AND METHOD OF INKING AND PRINTING | |
| DE2118019C3 (en) | Exhaust process for dyeing synthetic fiber materials | |
| DE2447610C3 (en) | Process for the production of anthraquinone dyes and their use | |
| DE2060565C3 (en) | Process for dyeing textiles made of polyester or cellulose triacetate | |
| DE1469745B2 (en) | Process for coloring fiber materials which consist of or contain high polymer, linear polyesters | |
| DE2607966A1 (en) | BENZOTHIOXANTHENS, THE PROCESS FOR THEIR MANUFACTURING AND THEIR USE AS COLORING MATTER |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PUAI | Public reference made under article 153(3) epc to a published international application that has entered the european phase |
Free format text: ORIGINAL CODE: 0009012 |
|
| 17P | Request for examination filed | ||
| AK | Designated contracting states |
Designated state(s): BE CH DE FR GB IT NL |
|
| ITF | It: translation for a ep patent filed |
Owner name: ING. C. GREGORJ S.P.A. |
|
| GRAA | (expected) grant |
Free format text: ORIGINAL CODE: 0009210 |
|
| AK | Designated contracting states |
Designated state(s): BE CH DE FR GB IT NL |
|
| ET | Fr: translation filed | ||
| REF | Corresponds to: |
Ref document number: 2964858 Country of ref document: DE Date of ref document: 19830324 |
|
| PGFP | Annual fee paid to national office [announced via postgrant information from national office to epo] |
Ref country code: CH Payment date: 19831124 Year of fee payment: 5 |
|
| PGFP | Annual fee paid to national office [announced via postgrant information from national office to epo] |
Ref country code: BE Payment date: 19841231 Year of fee payment: 6 |
|
| PGFP | Annual fee paid to national office [announced via postgrant information from national office to epo] |
Ref country code: NL Payment date: 19861130 Year of fee payment: 8 |
|
| PG25 | Lapsed in a contracting state [announced via postgrant information from national office to epo] |
Ref country code: CH Effective date: 19871130 Ref country code: BE Effective date: 19871130 |
|
| BERE | Be: lapsed |
Owner name: BAYER A.G. Effective date: 19871130 |
|
| PG25 | Lapsed in a contracting state [announced via postgrant information from national office to epo] |
Ref country code: NL Effective date: 19880601 |
|
| NLV4 | Nl: lapsed or anulled due to non-payment of the annual fee | ||
| REG | Reference to a national code |
Ref country code: CH Ref legal event code: PL |
|
| ITTA | It: last paid annual fee | ||
| PGFP | Annual fee paid to national office [announced via postgrant information from national office to epo] |
Ref country code: DE Payment date: 19921021 Year of fee payment: 14 |
|
| PG25 | Lapsed in a contracting state [announced via postgrant information from national office to epo] |
Ref country code: DE Effective date: 19940802 |
|
| PGFP | Annual fee paid to national office [announced via postgrant information from national office to epo] |
Ref country code: FR Payment date: 19941027 Year of fee payment: 16 |
|
| PGFP | Annual fee paid to national office [announced via postgrant information from national office to epo] |
Ref country code: GB Payment date: 19941111 Year of fee payment: 16 |
|
| PG25 | Lapsed in a contracting state [announced via postgrant information from national office to epo] |
Ref country code: GB Effective date: 19951121 |
|
| GBPC | Gb: european patent ceased through non-payment of renewal fee |
Effective date: 19951121 |
|
| PG25 | Lapsed in a contracting state [announced via postgrant information from national office to epo] |
Ref country code: FR Effective date: 19960731 |
|
| REG | Reference to a national code |
Ref country code: FR Ref legal event code: ST |
|
| PLBE | No opposition filed within time limit |
Free format text: ORIGINAL CODE: 0009261 |
|
| STAA | Information on the status of an ep patent application or granted ep patent |
Free format text: STATUS: NO OPPOSITION FILED WITHIN TIME LIMIT |