EP0055694B1 - Procédé de teinture et d'impression de matières à base de cellulose et de tissus à base de mélanges cellulose/polyester - Google Patents
Procédé de teinture et d'impression de matières à base de cellulose et de tissus à base de mélanges cellulose/polyester Download PDFInfo
- Publication number
- EP0055694B1 EP0055694B1 EP81810513A EP81810513A EP0055694B1 EP 0055694 B1 EP0055694 B1 EP 0055694B1 EP 81810513 A EP81810513 A EP 81810513A EP 81810513 A EP81810513 A EP 81810513A EP 0055694 B1 EP0055694 B1 EP 0055694B1
- Authority
- EP
- European Patent Office
- Prior art keywords
- vatting
- hydrogen
- accelerator
- group
- alkyl
- 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
- 0 *C(CO1)OS1=O Chemical compound *C(CO1)OS1=O 0.000 description 3
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
- D06P1/22—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 vat dyestuffs including indigo
- D06P1/221—Reducing systems; Reducing catalysts
-
- 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
- D06P1/30—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 sulfur dyes
Definitions
- the invention relates to a process for dyeing or printing cellulosic materials or cellulose / polyester blended fabrics using specific organic vatting accelerators, also vat or sulfur dye preparations which contain vatting accelerators of this type, and dye baths, printing pastes and reduction baths for carrying out the process.
- reducing agents for single-bath dyeing of cellulose-containing textile material with vat and / or sulfur dyes DE-A-2 350 961.
- the combination consists of a reducing agent obtained by condensing ketones with sodium dithionite and basic nitrogen-containing compounds and nitrophenol. This specific combination of reducing agents enables the dyeing of cellulose textile material by the one-bath block-steaming process or by the cold residence process.
- FR-A-2 250 848 describes a process for dyeing polyamide fiber material with sulfur dyes.
- Polyamide materials are difficult or impossible to dye with the sulfur dyes that are commonly used.
- esters of aromatic or aliphatic carboxylic acids for example benzoic acid or terephthalic acid esters or also acetic acid or propionic acid esters.
- FR-A-1 393 050 a process for dyeing or printing cellulose fiber material with water-soluble sulfur dyes is known.
- the dyes are then applied in the form of an aqueous preparation which, in addition to the dye, contains a compound having a thiocarbonyl and / or sulfhydryl function or can be converted into a thiocarbonyl derivative or thiol.
- a compound having a thiocarbonyl and / or sulfhydryl function or can be converted into a thiocarbonyl derivative or thiol.
- Examples include thioacetamide, thiourea, 2,4,6-trimercapto-1,3,5-triazine, mercaptobenzothiazole, dithiocarbamic acid or esters of thiocarbamic acid.
- vatting accelerators A whole series of compounds and their use as vatting accelerators are thus described in the prior art, but only a few substances have a sufficient range of use and enable a sufficiently good and rapid distribution of the vat and sulfur dyes in the dye liquor, printing paste or corresponding preparation forms.
- the aids are tailored to a small class of dyes or special dyeing processes.
- the known linking accelerators e.g. are difficult to access synthetically or have other disadvantages, e.g. insufficient effectiveness with different dyeing processes (e.g. poor effectiveness in the pad-steam dyeing process compared to printing), high price and sometimes dark inherent color e.g. of many quinone compounds, as well as nuances, such as. B. when using anthraquinones.
- the heavy metal compounds or thiourea they are less suitable from an ecological point of view and polyamines are only effective at high concentrations in the dye bath.
- the object of the invention was therefore to find vatting accelerators which do not have the disadvantages mentioned above and to develop a dyeing or printing process for cellulose and cellulose / polyester blended fabrics according to which a rapid and as complete as possible even with fast-running continuous dyeing processes The dyes are reduced, thus ensuring a good color yield.
- vatting accelerators or mixtures thereof are used as described below.
- These specific vatting accelerators are known per se as antioxidants, have an excellent effectiveness, are inexpensive and do not have the disadvantages mentioned at the outset. They can either be present in a vat or sulfur dye preparation, or can be added to the dye bath or reduction bath or the printing paste.
- R 1 , R 2 and R 3 in the meaning of a C 1 -C 12 alkyl group can be unbranched or branched. It is, for example, the methyl group, ethyl group, n-propyl group, isopropyl group, the n-, sec- or tert-butyl group, the n-, sec- or tert-amyl group, the n-, sec. or tert-hexyl group, the n-, sec- or tert-octyl group or the n-, sec- or tert-dodecyl group.
- R 1 , R 2 and R 3 represent, for example, the methoxy, ethoxy, n- or iso-propoxy and n- or iso-butoxy group.
- benzyl radical or Phenethyl radicals are suitable, for example: halogen, such as F, CI or Br, the OH group, C 1 -C 12 alkyl, preferably C 1 -C 4 alkyl (branched or unbranched) or C 1 -C 4 alkoxy (branched or unbranched).
- the substituents R 1 to R 3 have the following meanings: C 1 to C 5 alkyl, -CH 2 0H, hydrogen, halogen, OH, C 1 to C 4- alkoxy, benzyl, Cyclohexyl or the group again with the condition that if one of the radicals R 1 , R 2 or R 3 is -OH or -CH 3 , at most one of the remaining two radicals is hydrogen and also with the proviso that all three radicals R 1 to R 3 are not mean hydrogen at the same time.
- vatting accelerators of the formula (A) are used in which the radicals R 1 to R 3 are independently of one another: C 1 to C 4 alkyl, hydrogen, chlorine, hydroxy or benzyl, with the condition that R 1 , R 2 and R 3 do not simultaneously represent hydrogen and furthermore, in the event that one of the radicals R 1 to R 3 is an —OH or CH 3 group, means at most one of the remaining two radicals hydrogen.
- the type (A) compounds mentioned are known and can be prepared by known methods.
- a further class of compounds are the compounds of group (A) which are linked to an organic radical via a bridge member R ' 3 instead of the substituent R 3 .
- These are compounds of the formula organic radical in which R 1 and R 2 have the meaning given above, m is a number 1 or 2 and R ' 3 is any bridging element, for example the radical of an inorganic or organic acid or the radical of an aldehyde, a styrene or an olefin, and preferably a Group in which R 4 is independently hydrogen or C 1 -C 4 alkyl.
- R 1 , R z and R ' 3 have the meanings given above and X is an aliphatic bridge member, preferably - (CH 2 ) 2 COO-CH 2 , m is a number 1 or 2 and n is a number 1 to 4 and p is a number 1 to 3 mean.
- This group includes the partial or full esters of compounds of type (A) with inorganic and organic acids, e.g. with phosphoric acid, corresponding mono-, di- or trisphosphites, or with isocyanuric acid.
- inorganic and organic acids e.g. with phosphoric acid, corresponding mono-, di- or trisphosphites, or with isocyanuric acid.
- Such connections are e.g. the tris (3,5-di-tert-butyl-4-hydroxyphenyl) phosphite.
- Group B also includes those compounds which are formed by condensation of compounds of type A with, for example, aldehydes, such as formaldehyde or crotonaldehyde, or also reaction products of compounds (A) with, for. B. styrene and its derivatives or with olefins.
- A is the direct bond or a divalent bridge member of the formula where R 4 is independently hydrogen or C 1 -C 4 alkyl, and R s and R 6 are independently: C 1 -C 12 alkyl, C 3 -C 12 alkenyl, halogen, C 1 -C 4 - Alkoxy, optionally substituted phenyl, cyclohexyl, benzyl, phenethyl, hydrogen, S0 3 H, COOH or CONH 2 .
- Preferred from these classes of compounds (A) and (B) are those compounds which contain a sterically hindered phenol group, in particular those in which the o-position to the OH group is occupied by a tertiary alkyl radical.
- R 11 is a C 1 -C 4 -alkyl group or a C 1 -C 3 -alkoxy group, this can be unbranched or branched.
- R 12 is a C 1 -C 12 alkyl group, this can be unbranched or branched; for example, the methyl, ethyl, n or iso-hexyl and n or iso-octyl group are mentioned.
- these are dihydroxy and, on the other hand, hydroxyamino naphthalenes, where the two OH or. OH and NH 2 groups are preferably in the 1,6, 1,8, 2,5 and 2,7 positions.
- R 16 represents an unbranched or branched C 1 -C 4 alkyl group, such as the methyl, ethyl, n or iso-propyl or n, sec. or tert-butyl group. These compounds are known and can be prepared by known methods. A preferred compound from this class is 4-hydroxy-acetophenone.
- Z is independently a bridge member of the formula or p is a number from 2-6, R 28 and R 29 independently of one another hydrogen, C 1 -C 6 alkyl (unbranched or branched) or C 1 -C 3 alkoxy (unbranched or branched), R 23 , R 24, R 2s and R 27 independently of one another hydrogen, C 1 -C 12 alkyl (unbranched or branched), C 1 -C 12 hydroxyalkyl, optionally substituted phenyl or cyclohexyl, a- or ⁇ -naphthyl or benzyl and R 26 C 1 -C 12 -alkyl (unbranched or branched) or optionally substituted phenyl, a- or ⁇ -naphthyl; Cyclohexyl or benzyl, where R 21 and R 24 or R 25 and R 26 do not simultaneously denote hydrogen, with the condition that when Z is - (CH 2 ) p-, R 23 ,
- R 23 , R 24 , R 25 , R 26 and R 17 OH, halogen (F, Cl, Br), NH 2 and C 1 -C 4 alkyl.
- R 30 represents an unbranched or branched C 1 -C 12 alkyl group, such as the methyl, ethyl, n or iso-propyl, n or iso-hexyl or n or iso-octyl group.
- the compounds mentioned under A) to I) are generally easily accessible and are notable for good distributability in the dye preparations, dye baths or reduction baths and printing pastes.
- the compounds mentioned should be water-soluble and / or soluble in an alkaline reductive bath (ph ⁇ 12). If they do not meet these solubility requirements, it is advisable to use these compounds before their use, e.g. to be ground with an anionic dispersing agent to a grain size of ⁇ 5 ⁇ m, in particular about 11 m. In principle, this is done in such a way that the vatting accelerator or a mixture thereof with a dispersant, e.g.
- naphthalenesulfonic acid / formaldehyde condensation product for example by joint wet grinding in a corundum disk mill, ball mill, agitator mill, sand mill or other grinding units, optionally with subsequent drying of the mixture, e.g. in an atomizing dryer.
- the phenols and amines according to groups A), B), C) and G) are preferably used as vatting accelerators.
- vatting accelerators are advantageously used in an amount of 0.5 to 10% by weight, based on the dye, or in an amount of 0.05 to 1 g per liter of reduction bath.
- the term process for dyeing or printing cellulosic materials or cellulose / polyester blended fabrics in the present case is to be understood as general dyeing and printing processes with which vat and sulfur dyes are normally applied to the textile materials mentioned.
- the dyeing process is both a pull-out and a continuous process.
- pull-out process in the jigger, in the reel runner and in the jet dyeing machine the pad-jig process, the standfast process, the semi-pigmentation process, the block fixing process, e.g. B. the Einbadklotzdampf psychologist, the pad-roll process, the pad-roll process with intermediate drying, the wet steam process and especially the pad-steam process.
- As printing processes e.g. called: single-phase and two-phase development processes.
- the vatting accelerators are contained in the preparations in a concentration of 0.1 to 20% by weight, in particular 0.5 to 10% by weight, based on the dye.
- the dye preparations usually also contain anionic dispersants or possibly nonionic fillers, preferably in amounts of 0.5 to 80% by weight. Dispersants of this type are primarily used as described in DE-A-2 816 539. Further additives are the auxiliaries generally contained in dye preparations, such as humectants, antifoams, preservatives, wetting agents, leveling agents, thickeners, etc.
- vat and sulfur dyes are primarily indanthrones, flavanthrones, pyranthrones, violanthrones, isoviolanthrones, benzanthrones, nitrogen-substituted imides of perylene tetracarboxylic acid, acridones, anthraquinone oxazoles, anthraquinone thiazoles and compounds that are derived primarily from anthraquinone.
- the invention also relates to the dye baths and printing pastes, and the reduction baths as such.
- the dyebaths or printing pastes are produced in a simple manner by dissolving a vat or sulfur dye preparation which already contains the vatting accelerator in the dyebath or by incorporating them in a suitable thickener.
- the textile material can also initially only be impregnated or printed with the dye, then optionally dried and then the dye on the fabric can be vetted in a reduction bath containing the vatting accelerator.
- the linking accelerators are substances which belong to the compound classes already described in detail. The compounds are used individually or in a mixture, specifically per liter of reduction bath in an amount of 0.01 to 5 g, preferably 0.05 to 1 g.
- the reduction baths contain, in addition to the vatting accelerator, a reducing agent, e.g. B. sodium dithionite, sodium formaldehyde sulfoxylate of thiourea dioxide, and alkali, especially sodium hydroxide solution or potassium hydroxide solution.
- a reducing agent e.g. B. sodium dithionite, sodium formaldehyde sulfoxylate of thiourea dioxide, and alkali, especially sodium hydroxide solution or potassium hydroxide solution.
- Parts mean parts by weight.
- the cotton fabric is then steamed in the steamer at 100 ° C for 30 seconds. Then rinsed as usual, with 3 ml / l H 2 0 2 30%, oxidized for 15 minutes at 50 ° C, rinsed and for 15 minutes at cooking temperature with 2 g / i of an anionic detergent and 1 g / l soda calc. soaped. A blue coloration is obtained which is more intense in color than a comparison coloration without the addition of 30% aqueous dispersion of tetrakis [methylene-3- (3 ', 5'-di-tert-butyl-4'-hydroxyphenyl) propionate ]-methane.
- Washed-out cotton fabric is padded with this dye liquor and treated as in Example 4 until the dyeing is finished.
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- Engineering & Computer Science (AREA)
- Textile Engineering (AREA)
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Coloring (AREA)
Claims (17)
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CH964480 | 1980-12-30 | ||
CH9644/80 | 1980-12-30 |
Publications (3)
Publication Number | Publication Date |
---|---|
EP0055694A2 EP0055694A2 (fr) | 1982-07-07 |
EP0055694A3 EP0055694A3 (en) | 1983-01-19 |
EP0055694B1 true EP0055694B1 (fr) | 1986-06-04 |
Family
ID=4354139
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
EP81810513A Expired EP0055694B1 (fr) | 1980-12-30 | 1981-12-22 | Procédé de teinture et d'impression de matières à base de cellulose et de tissus à base de mélanges cellulose/polyester |
Country Status (5)
Country | Link |
---|---|
US (2) | US4519805A (fr) |
EP (1) | EP0055694B1 (fr) |
JP (2) | JPS57133281A (fr) |
DE (1) | DE3174788D1 (fr) |
ZA (1) | ZA818967B (fr) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN104372685A (zh) * | 2014-12-05 | 2015-02-25 | 江苏太子鳄服饰有限公司 | 布料的耐洗印染方法 |
Families Citing this family (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE3704125A1 (de) * | 1987-02-11 | 1988-08-25 | Basf Ag | Verwendung von cyclischen estern der schwefligen saeure beim faerben von textilmaterialien aus polyamid und verfahren zum faerben |
JPS63271963A (ja) * | 1987-04-28 | 1988-11-09 | Nec Corp | 半導体装置の製造方法 |
US4886518A (en) * | 1987-10-01 | 1989-12-12 | Ciba-Geigy Corporation | Dyeing cellulose fibres without incurring ending with colorless pyrimidine, triazine, aromatic, furfuryl or quinolinyl compound |
CN1029227C (zh) * | 1989-02-08 | 1995-07-05 | 大制药株式会社 | 苯衍生物的制备方法 |
US5108505A (en) * | 1990-05-16 | 1992-04-28 | Hewlett-Packard Company | Waterfast inks via cyclodextrin inclusion complex |
IT1271814B (it) * | 1994-12-28 | 1997-06-09 | Alpi Spa | Tintura di fogli di legno mediante coloranti appartenenti alla classe "al tino". |
US5961670A (en) * | 1995-05-03 | 1999-10-05 | Clariant Finance (Bvi) Limited | Sulfur dyes |
HUP0102869A2 (hu) | 1998-06-23 | 2002-02-28 | Henkel Kommanditgesellschaft Auf Aktien | Keratin szálak színezésére szolgáló festőanyag |
Citations (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CH886560A4 (fr) * | 1959-08-08 | 1964-03-13 |
Family Cites Families (35)
Publication number | Priority date | Publication date | Assignee | Title |
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US1803219A (en) * | 1931-04-28 | Formerly saostooz | ||
GB1130908A (fr) * | ||||
GB354777A (en) * | 1930-03-10 | 1931-08-10 | James Morton | Improvements in and relating to dyeing with vat dyestuffs |
US2074150A (en) * | 1934-05-01 | 1937-03-16 | Nat Aniline & Chem Co Inc | Vat dye assistants and method of using |
US2069215A (en) * | 1934-08-18 | 1937-02-02 | Du Pont | Printing process and composition therefor |
CH192294A (de) * | 1936-01-15 | 1937-07-31 | Chem Ind Basel | Präparat zum Drucken von Textilstoffen. |
US2087866A (en) * | 1937-03-17 | 1937-07-20 | Du Pont | Vat dyestuff preparations |
FR835854A (fr) * | 1937-03-30 | 1939-01-05 | Durand & Huguenin Sa | Procédé pour la teinture et l'impression de la soie naturelle avec les éthersels de dérivés leuconiques de colorants à cuve |
US2256809A (en) * | 1938-11-28 | 1941-09-23 | Nat Aniline & Chem Co Inc | Production of resist effects |
US2256806A (en) * | 1938-11-28 | 1941-09-23 | Nat Aniline & Chem Co Inc | Vat dye composition |
GB616440A (en) * | 1946-11-02 | 1949-01-21 | Alan Stanley Pern | Process for dyeing |
DE912450C (de) * | 1951-12-18 | 1954-05-31 | Bayer Ag | Verfahren zum Faerben oder Bedrucken von Acrylnitrilpolymerisaten mit Kuepenfabstoffen |
DE896335C (de) * | 1951-12-29 | 1953-11-12 | Basf Ag | Verfahren zum Verkuepen von Kuepenfarbstoffen |
FR1068097A (fr) * | 1952-10-03 | 1954-06-22 | Southern Dyestuff Corp | Colorants de cuve liquides concentrés |
US2852331A (en) * | 1955-06-01 | 1958-09-16 | Gen Aniline & Film Corp | Low viscosity stabilized vat dye pastes |
US2921830A (en) * | 1956-07-31 | 1960-01-19 | Gen Aniline & Film Corp | Hydron blue dyestuff compositions |
US2893813A (en) * | 1956-07-31 | 1959-07-07 | Gen Aniline & Film Corp | Indo-carbon black dyestuff compositions |
BE571349A (fr) * | 1957-09-19 | |||
DE1086209B (de) * | 1959-04-18 | 1960-08-04 | Basf Ag | Druckpasten fuer das Direkt- oder AEtzdruckverfahren |
DE1163284B (de) * | 1960-10-15 | 1964-02-20 | Hoechst Ag | Verwendung von Methylendiarylverbindungen als Dispergiermittel fuer in Wasser unloesliche oder schwer loesliche Farbstoffe |
DE1286499B (de) * | 1962-01-25 | 1969-01-09 | Bayer Ag | Egalisiermittel fuer das Faerben von Polyestergebilden |
US3201190A (en) * | 1962-05-28 | 1965-08-17 | Eastman Kodak Co | Dyed cellulose ester textile materials resistant to chlorine fading |
GB982500A (en) * | 1963-07-12 | 1965-02-03 | Metal Hydrides Inc | Improvements in dyeing with acid leuco vat dyes |
FR1393050A (fr) * | 1964-05-11 | 1965-03-19 | Hoechst Ag | Procédé de teinture et d'impression de matières textiles en fibres de cellulose naturelle ou régénérée |
US3532455A (en) * | 1967-09-19 | 1970-10-06 | American Cyanamid Co | Method for producing sulfurized vat dyes by thionation and products thereof |
DE2229130A1 (de) * | 1972-06-15 | 1974-01-10 | Basf Ag | Schnellfixierverfahren zum kontinuierlichen faerben von stoffbahnen aus cellulose enthaltendem fasermaterial mit kuepenfarbstoffen |
DE2350961A1 (de) * | 1973-10-11 | 1975-04-24 | Basf Ag | Reduktionsmittelkombination zum einbadigen faerben von cellulose enthaltendem textilmaterial mit kuepen- und/oder schwefelfarbstoffen |
DE2356548A1 (de) * | 1973-11-13 | 1975-06-26 | Cassella Farbwerke Mainkur Ag | Verfahren zum faerben von polyamidfasern mit schwefelfarbstoffen |
DE2416300A1 (de) * | 1974-04-04 | 1975-10-16 | Cassella Farbwerke Mainkur Ag | Verfahren zum faerben von zellulosehaltigen textilmaterialien mit schwefelfarbstoffen |
CH598404B5 (fr) * | 1975-04-04 | 1978-04-28 | Ciba Geigy Ag | |
DE2525021A1 (de) * | 1975-06-05 | 1976-12-23 | Hoechst Ag | Verfahren und mittel zur herstellung von direktdrucken und buntaetzen mit kuepen- oder schwefelfarbstoffen |
DE2628903A1 (de) * | 1976-06-28 | 1978-01-05 | Boc Ltd | Dithionit-stabilisator-zubereitung, verfahren zu ihrer herstellung und verwendung des stabilisators in der zubereitung |
DE2657774C2 (de) * | 1976-12-21 | 1982-06-16 | Hoechst Ag, 6000 Frankfurt | Verwendung eines wasserlöslichen nicht-ionogenen Polyglykoläthers als Mahlhilfsmittel und wäßrige Zubereitungen von in Wasser schwer- bis unlöslichen Farbstoffen |
DE2901461A1 (de) * | 1979-01-16 | 1980-07-24 | Hoechst Ag | Verwendung oxalkylierter novolakharze als praeparationsmittel fuer dispersionsfarbstoffe und damit hergestellte zubereitungen |
GB2114166B (en) * | 1982-02-03 | 1985-08-14 | Sandoz Ltd | Level dyeing of polyester materials |
-
1981
- 1981-12-22 EP EP81810513A patent/EP0055694B1/fr not_active Expired
- 1981-12-22 DE DE8181810513T patent/DE3174788D1/de not_active Expired
- 1981-12-29 ZA ZA818967A patent/ZA818967B/xx unknown
- 1981-12-29 JP JP56216091A patent/JPS57133281A/ja active Granted
- 1981-12-29 US US06/335,428 patent/US4519805A/en not_active Expired - Fee Related
-
1988
- 1988-03-08 US US07/169,093 patent/US4886549A/en not_active Expired - Fee Related
-
1990
- 1990-08-06 JP JP2207964A patent/JPH0376876A/ja active Granted
Patent Citations (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CH886560A4 (fr) * | 1959-08-08 | 1964-03-13 |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN104372685A (zh) * | 2014-12-05 | 2015-02-25 | 江苏太子鳄服饰有限公司 | 布料的耐洗印染方法 |
Also Published As
Publication number | Publication date |
---|---|
EP0055694A2 (fr) | 1982-07-07 |
DE3174788D1 (en) | 1986-07-10 |
ZA818967B (en) | 1982-11-24 |
JPS57133281A (en) | 1982-08-17 |
US4886549A (en) | 1989-12-12 |
JPH0423031B2 (fr) | 1992-04-21 |
US4519805A (en) | 1985-05-28 |
JPH0329827B2 (fr) | 1991-04-25 |
JPH0376876A (ja) | 1991-04-02 |
EP0055694A3 (en) | 1983-01-19 |
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