EP0354397B1 - Traitement de laine et fibres polyamidiques - Google Patents
Traitement de laine et fibres polyamidiques Download PDFInfo
- Publication number
- EP0354397B1 EP0354397B1 EP89113507A EP89113507A EP0354397B1 EP 0354397 B1 EP0354397 B1 EP 0354397B1 EP 89113507 A EP89113507 A EP 89113507A EP 89113507 A EP89113507 A EP 89113507A EP 0354397 B1 EP0354397 B1 EP 0354397B1
- Authority
- EP
- European Patent Office
- Prior art keywords
- acid
- weight
- wool
- process according
- ketene
- 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 - Lifetime
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
- D06M13/10—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 oxygen
- D06M13/12—Aldehydes; Ketones
- D06M13/13—Unsaturated aldehydes, e.g. acrolein; Unsaturated ketones; Ketenes ; Diketenes
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S8/00—Bleaching and dyeing; fluid treatment and chemical modification of textiles and fibers
- Y10S8/92—Synthetic fiber dyeing
- Y10S8/924—Polyamide fiber
Definitions
- aryl is preferably phenyl or naphthyl with aralkyl for benzyl.
- the aromatic radicals can carry substituents, for example alkyl radicals with 1-12 C atoms.
- the ketene dimers (I) are prepared by known processes, e.g. by splitting off hydrogen chloride from carboxylic acid chlorides in the presence of tertiary amines by the process of DE-A-2 335 488.
- ketene dimers (I) are octyl, decyl, dodecyl, tetradecyl, hexadecyl, octadecyl, eicosyl, docosyl, tetracosyl and cyclohexyl ketene dimers and dimers substituted with an aromatic hydrocarbon radical, for example phenyl, benzyl or .beta.-Naphthylketendimere, as well as ketene dimers, which are derived from montanic acid, naphthenic acid, ⁇ 9,10-decylenic, ⁇ 9,10-Dodecylenklare, palmitoleic acid, oleic acid, petroselinic acid, vaccenic acid, linoleic acid, linolenic acid, eleostearic acid, parinaric acid, gadoleic acid, arachidonic acid, and ceto
- the ketene dimers (I) are preferably applied in the form of their aqueous preparations. Depending on the nature of (I), these can be settings of the liquid-liquid type or of the solid-liquid type, for which both the term "emulsion" is chosen here.
- aqueous emulsions are known. They advantageously contain emulsifying agents and, if appropriate, further cationic, nonionic or anionic surface-active substances and liquid hydrocarbons.
- Emulsifying agents are understood to be agents which are used on the basis of their protective colloid properties or to increase the viscosity and thus the stability of the ketene dimer emulsions.
- Suitable emulsifying aids are, for example, cationic amino-modified starch (DE-A-1 148 130), polyvinyl alcohols (DE-A-2 306 542), polyvinyl lactams (DE-A-2 514 128) and carboxymethyl cellulose (US-A-2 762 270).
- Cationic emulsifiers such as N-octyldecylpyridinium chloride (US Pat. No. 3,046,186), nonionic emulsifiers which can be obtained by adding ethylene oxide to hydroxyl groups and compounds containing relatively long hydrocarbons, such as saturated and unsaturated alcohols having 12 to 18 carbon atoms or alkylated, can be used as surface-active substances
- Phenols obtained (DE-A-2 533 411) or anionic dispersants from the group of sodium lignin sulfonates and aromatic naphtholsulfonic acid-formaldehyde condensates (DE-A-2 951 507) can be used.
- the emulsions advantageously contain 0.5 to 30 percent by weight, based on the weight of the emulsion, but preferably 1 to 15 percent by weight of ketene dimer (I).
- the emulsifying aids are used in an amount of 0.2 to 15 percent by weight.
- the amount used is preferably 0.5 to 6 percent by weight.
- the amounts of the surface-active substances are such that stable emulsions are obtained over a long period of time.
- alkyl ketene dimers, emulsifying aids and surface-active substances are to be coordinated in each individual case so that usable, dilutable and pourable aqueous emulsions are present.
- the stability of the aqueous emulsions can optionally be considerably increased by adjusting to a pH of 2.0 to 5.5, preferably 3.0 to 4.5 with mineral acids or C1-C4 carboxylic acids.
- the emulsions can also contain other textile auxiliaries such as dirt, oil and water repellants, fungicides, foaming agents or anti-foaming agents.
- a melt of the ketene dimer to which about 5 to 30% by weight of a liquid hydrocarbon such as toluene, cyclohexane, octane or hydrocarbon mixtures can be added as an inert solvent, is dissolved in a solution of the emulsifying aid at temperatures from 40 to 90 ° C stirred in, optionally homogenized with a homogenizer, and cooled with stirring.
- a liquid hydrocarbon such as toluene, cyclohexane, octane or hydrocarbon mixtures
- the materials used for the treatment can be wool and synthetic polyamides such as polymers of ⁇ -caprolactam and polymers of dicarboxylic acid and diamines, e.g. act from adipic acid and hexamethylenediamine.
- the synthetic polyamides can also carry acidic groups such as sulfonic acid groups and can therefore be dyed with cationic dyes.
- Suitable dyes are the dyes usually used for dyeing fibers containing polyamide groups, for example acid dyes, metal complex dyes such as 1: 1 metal complex dyes, which can contain water-solubilizing groups such as sulfonic acid or carboxylic acid groups or also sulfonamide or alkylsulfone residues, as well as reactive dyes and cationic dyes, for example un Ullmann's Encyclopedia of Technical Chemistry, 3rd edition 1970, supplement volume p. 225 are questionable.
- the substrates can be in the form of flake, sliver, yarn or piece goods.
- the method for treating carpets is preferably used. They can be in the form of web, warp and tufted goods.
- the aqueous emulsions are particularly advantageously used for the treatment of velor and loop goods, the pile of which consists of wool or synthetic polyamides.
- the base material can e.g. consist of polypropylene fabrics or polyisopropylene or polyester fleece.
- the method according to the invention ensures optimal pole development. This is to be understood to mean that the pile opens and thus gains volume, sets up in the direction specified by the weaving, knitting and tufting settings, and that the pile surface appears even without individual fibers emerging from the fiber structure.
- the substrate has a voluminous and pleasant grip.
- the process can be carried out continuously and batchwise. Continuous treatments by immersion, padding, spraying and foam application methods are preferred.
- the liquor ratio is in particular 1: 1-5.
- the heat treatment following the liquor application is preferably carried out for 1-15 minutes at 100-120 ° C, for example at steam temperatures around 100 ° C.
- the preferred conditions in the discontinuous exhaust process are: liquor ratio 1: 10-40, treatment time 1-2 hours and temperature 65-95 ° C.
- the amount of ketene dimers (I) used is preferably 0.01-5% by weight, in particular 0.05-1% by weight, based on wool or synthetic polyamide.
- the process according to the invention can be carried out simultaneously with the dyeing or finishing with further agents or according to these processes.
- aqueous ketene dimer emulsions are known from the publications mentioned above and have hitherto been used as sizing agents for paper. Surprisingly, it has now been found that they give wool and synthetic polyamide materials advantageous properties.
- Example 2 Following the procedure of Example 1, 250 g of behenic acid chloride are reacted in 600 g of toluene and 80.7 g of triethylamine. The reaction mixture is mixed with 120 g of water and 12 g of concentrated hydrochloric acid and stirred at 50 ° C for 30 minutes. After phase separation, the toluene is distilled off in vacuo. The product, 213 g of ketene dimer (yield 94.8% of theory), has a melting point of 63-64 ° C.
- a mixture of 100 g of Cato 110 (Roquett, cationic starch) and 1500 g of water are stirred at 90-95 ° C for 1 hour.
- 25 g of acetic acid and 19.2 g of a phenol-bisulfite-urea-formaldehyde condensate are added to the solution, which has been cooled to 70 ° C., and as an anionic dispersant.
- a melt of 70 g of 240 g of ketene dimer of stearic acid and 48 g of white oil is run into the starch solution and then homogenized for 2-3 minutes at a pressure of 40 bar and 70 ° C. in a jet disperser.
- the product is diluted with 1300 g of water and cooled to 30 ° C.
- the ketene dimer of behenic acid is emulsified in the same way.
- the emulsification process corresponds to that described in Example 3.
- the treatment liquor contains per liter
- the goods speed is 12 m / min.
- the fleet order is 270% by weight of the pile weight.
- the steaming time is 3 minutes.
- the substrate is dewatered and at 110 ° C dried.
- the fabric treated with recipe A shows a depressed, flat portion of velor, a hard handle and a straw character.
- the fabric treated with recipe B shows an almost vertical velor, which has a good orientation according to the tufting setting.
- the velor top is even, with almost no protruding fibers.
- the grip character is voluminous.
- the dyes are chosen so that the color differences between the fiber types are not shifted.
- Blocking aids such as example 7 1.5 1.5 Dispersant of the formula C17H33-CH2- (O-CH2-CH2-) OH 45-50 0.5 0.5 Thickener based on powdered meal ether 3.0 3.0 Acetic acid (60%) 5.5 5.5 Preparation according to example 4 - 7.5.
- the liquor is applied with 500% by weight of the pile weight and treated as described under 7.
- the color shade differentiation of recipes A and B is the same.
- the quality loss is as described in Example 7.
- a carpet product with a polyamide 6,6-pole and a pile weight of 580 g / m2 is dyed according to the method of example 7 with the formulation A described there. After drying and shearing, the carpet is provided with a dirt, oil and water-repellent finish on a foam application system.
- the finishing agent is a polymer of 35% by weight of units of the formula and 65% by weight units of the formula
- the amine oxide of an alkyl ether of tri (hydroxyethyl) amine is used as the foaming agent.
- the liquor is foamed to a foam liter weight of 25 g using a static foam mixer and pressed onto the carpet pile until the wet weight increases by 20%.
- the goods equipped with Fleet A show a hard, cracked and flat pile failure, which is typical of the stress and non-development of the pile on a dyeing system.
- Equipment with fleet B. shows a full, voluminous and soft textile character with an almost vertical pole.
- a carpet made of wool velor with a fiber covering of 950 g / m2 is used for the treatment.
- the wool was washed as a flock and bleached weakly. After spinning to a yarn, deepening to the carpet and application of a back coating, the goods are treated without the prior wet treatment according to the procedure described in Example 9.
- the evaluation of the goods gives the following result:
- the goods treated with the equipment fleet show a significantly denser pole surface than the untreated goods.
- the handle is also more voluminous and softer.
- a carpet is treated with a preparation according to example 5.
- the evaluation of the goods gives the following result:
- the goods treated with the equipment fleet show a significantly denser pole surface than the untreated goods.
- the handle is also more voluminous and softer.
- a carpet is treated with a preparation according to Example 6 according to the method described in Example 10.
Landscapes
- Engineering & Computer Science (AREA)
- Textile Engineering (AREA)
- Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
Claims (8)
- Procédé de traitement de laine et de fibres de polyamides synthétiques, caractérisé en ce qu'on utilise des dimères de cétènes de formule généraleR₁ et R₂ représentent indépendamment l'un de l'autre un reste alkyle ou alcényle ayant au moins 8 atomes de carbone, un reste cycloalkyle ayant au moins 6 atomes de carbone ou un reste aryle ou aralkyle.
- Procédé suivant la revendication 1, caractérisé en ce qu'on utilise des dimères de cétènes de formule (I) dans laquelle R₁ et R₂ sont des restes alkyle ou alcényle ayant 10 à 22 atomes de carbone.
- Procédé suivant la revendication 1, caractérisé en ce qu'on utilise les dimères de cétènes sous forme d'émulsions aqueuses.
- Procédé suivant la revendication 1, caractérisé en ce qu'on utilise des émulsions aqueuses qui contiennent 0,5 à 30 % en poids d'un dimère de cétène (I) et 0,2 à 15 % en poids d'une substance auxiliaire émulsionnante.
- Procédé suivant la revendication 1, caractérisé en ce qu'on utilise les dimères de cétènes en une quantité de 0,05 à 1 % en poids, par rapport à la fibre.
- Procédé suivant la revendication 1, caractérisé en ce qu'il est mis en oeuvre en continu.
- Procédé suivant la revendication 1, caractérisé en ce que la laine et les libres de polyamides synthétiques se présentent sous forme de matières pour tapis.
- Laine et matières en polyamides synthétiques, qui ont été traitées par le procédé suivant la revendication 1.
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE3826769A DE3826769A1 (de) | 1988-08-06 | 1988-08-06 | Behandlung von polyamidfasern |
DE3826769 | 1988-08-06 |
Publications (3)
Publication Number | Publication Date |
---|---|
EP0354397A2 EP0354397A2 (fr) | 1990-02-14 |
EP0354397A3 EP0354397A3 (en) | 1990-12-12 |
EP0354397B1 true EP0354397B1 (fr) | 1993-03-24 |
Family
ID=6360368
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
EP89113507A Expired - Lifetime EP0354397B1 (fr) | 1988-08-06 | 1989-07-22 | Traitement de laine et fibres polyamidiques |
Country Status (4)
Country | Link |
---|---|
US (1) | US5028236A (fr) |
EP (1) | EP0354397B1 (fr) |
JP (1) | JP2901650B2 (fr) |
DE (2) | DE3826769A1 (fr) |
Families Citing this family (11)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE69231379T2 (de) * | 1991-03-01 | 2001-03-01 | E.I. Du Pont De Nemours And Co., Wilmington | Oberflächenbehandelte aramidfasern und verfahren zu deren herstellung |
US5403392A (en) * | 1993-08-04 | 1995-04-04 | Ennis Herder, Inc. | High solids aqueous dispersions of hydrophobizing agents |
US5447689A (en) * | 1994-03-01 | 1995-09-05 | Actimed Laboratories, Inc. | Method and apparatus for flow control |
US5658377A (en) * | 1996-01-24 | 1997-08-19 | Ennis Herder, Inc. | Stable high solids aqueous dispersions of hydrophobizing agents |
US6156112A (en) * | 1998-02-12 | 2000-12-05 | Craig; Daniel H. | High solids aqueous dispersions of reactive hydrophobizing agents |
AT411734B (de) * | 1999-12-22 | 2004-05-25 | Atomic Austria Gmbh | Brettartiges gleitgerät, insbesondere schi oder snowboard |
DE10008930A1 (de) * | 2000-02-25 | 2001-08-30 | Basf Ag | Antiknitterausrüstung von cellulosehaltigen Textilien und Wäschenachbehandlungsmittel |
KR20030084355A (ko) * | 2002-04-26 | 2003-11-01 | 엘지이노텍 주식회사 | 내장형 커패시터와 이를 포함하는 적층기판 |
DE102010038887A1 (de) | 2010-08-04 | 2012-02-09 | Wacker Chemie Ag | β-Ketocarbonylquatverbindungen und Verfahren zu deren Herstellung |
DE102010063696A1 (de) | 2010-12-21 | 2012-06-21 | Wacker Chemie Ag | Zusammensetzungen enthaltend Quatverbindungen und Organopolysiloxane |
IN2014CN03735A (fr) | 2011-11-17 | 2015-09-04 | Basf Se |
Family Cites Families (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2171241A (en) * | 1936-05-12 | 1939-08-29 | Textile Foundation Washington | Silk |
US2482578A (en) * | 1947-04-24 | 1949-09-20 | Little Inc A | Treatment of wool |
US2672397A (en) * | 1952-08-22 | 1954-03-16 | Harold P Lundgren | Reaction of wool with beta-propiolactone and water |
US3002024A (en) * | 1957-03-12 | 1961-09-26 | Goodrich Co B F | Bis-ketenes and method of preparation |
JPS5943069B2 (ja) * | 1980-09-26 | 1984-10-19 | 日本合成化学工業株式会社 | 木材用接着剤 |
JPS57205583A (en) * | 1981-06-09 | 1982-12-16 | Nippon Synthetic Chem Ind | Treating agent for fiber product |
JPS5887395A (ja) * | 1981-11-19 | 1983-05-25 | 花王株式会社 | 製紙用サイズ剤組成物 |
-
1988
- 1988-08-06 DE DE3826769A patent/DE3826769A1/de not_active Withdrawn
-
1989
- 1989-07-22 DE DE8989113507T patent/DE58903869D1/de not_active Expired - Fee Related
- 1989-07-22 EP EP89113507A patent/EP0354397B1/fr not_active Expired - Lifetime
- 1989-08-04 JP JP1201493A patent/JP2901650B2/ja not_active Expired - Lifetime
- 1989-08-04 US US07/389,646 patent/US5028236A/en not_active Expired - Lifetime
Non-Patent Citations (1)
Title |
---|
Faserforschung und Textiltechnik, Band 22, 1971, Seiten 501-505, Deutscher Fachverlag, Frankfurt/Main, H.-H. Ulrich:"Modifizierungsreaktionen an Polyamidfäden. Eine Literaturübersicht" * |
Also Published As
Publication number | Publication date |
---|---|
JP2901650B2 (ja) | 1999-06-07 |
JPH0397960A (ja) | 1991-04-23 |
DE58903869D1 (de) | 1993-04-29 |
DE3826769A1 (de) | 1990-02-15 |
EP0354397A2 (fr) | 1990-02-14 |
US5028236A (en) | 1991-07-02 |
EP0354397A3 (en) | 1990-12-12 |
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