Nothing Special   »   [go: up one dir, main page]

EP0665311B1 - Fibres synthétiques cellulosiques aminées - Google Patents

Fibres synthétiques cellulosiques aminées Download PDF

Info

Publication number
EP0665311B1
EP0665311B1 EP95100299A EP95100299A EP0665311B1 EP 0665311 B1 EP0665311 B1 EP 0665311B1 EP 95100299 A EP95100299 A EP 95100299A EP 95100299 A EP95100299 A EP 95100299A EP 0665311 B1 EP0665311 B1 EP 0665311B1
Authority
EP
European Patent Office
Prior art keywords
cellulose
group
substituted
synthetic fibers
fibers
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
Application number
EP95100299A
Other languages
German (de)
English (en)
Other versions
EP0665311A1 (fr
Inventor
Andreas Dr. Schrell
Werner Hubert Dr. Russ
Bernd Dr. Huber
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Dystar Textilfarben GmbH and Co Deutschland KG
Original Assignee
Dystar Textilfarben GmbH and Co Deutschland KG
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Priority claimed from DE19944402711 external-priority patent/DE4402711A1/de
Priority claimed from DE19944422758 external-priority patent/DE4422758A1/de
Application filed by Dystar Textilfarben GmbH and Co Deutschland KG filed Critical Dystar Textilfarben GmbH and Co Deutschland KG
Publication of EP0665311A1 publication Critical patent/EP0665311A1/fr
Application granted granted Critical
Publication of EP0665311B1 publication Critical patent/EP0665311B1/fr
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

Links

Classifications

    • D—TEXTILES; PAPER
    • D01—NATURAL OR MAN-MADE THREADS OR FIBRES; SPINNING
    • D01F—CHEMICAL FEATURES IN THE MANUFACTURE OF ARTIFICIAL FILAMENTS, THREADS, FIBRES, BRISTLES OR RIBBONS; APPARATUS SPECIALLY ADAPTED FOR THE MANUFACTURE OF CARBON FILAMENTS
    • D01F8/00—Conjugated, i.e. bi- or multicomponent, artificial filaments or the like; Manufacture thereof
    • D01F8/02—Conjugated, i.e. bi- or multicomponent, artificial filaments or the like; Manufacture thereof from cellulose, cellulose derivatives, or proteins
    • D—TEXTILES; PAPER
    • D01—NATURAL OR MAN-MADE THREADS OR FIBRES; SPINNING
    • D01F—CHEMICAL FEATURES IN THE MANUFACTURE OF ARTIFICIAL FILAMENTS, THREADS, FIBRES, BRISTLES OR RIBBONS; APPARATUS SPECIALLY ADAPTED FOR THE MANUFACTURE OF CARBON FILAMENTS
    • D01F2/00—Monocomponent artificial filaments or the like of cellulose or cellulose derivatives; Manufacture thereof
    • D—TEXTILES; PAPER
    • D01—NATURAL OR MAN-MADE THREADS OR FIBRES; SPINNING
    • D01F—CHEMICAL FEATURES IN THE MANUFACTURE OF ARTIFICIAL FILAMENTS, THREADS, FIBRES, BRISTLES OR RIBBONS; APPARATUS SPECIALLY ADAPTED FOR THE MANUFACTURE OF CARBON FILAMENTS
    • D01F2/00—Monocomponent artificial filaments or the like of cellulose or cellulose derivatives; Manufacture thereof
    • D01F2/02—Monocomponent artificial filaments or the like of cellulose or cellulose derivatives; Manufacture thereof from solutions of cellulose in acids, bases or salts
    • D01F2/04—Monocomponent artificial filaments or the like of cellulose or cellulose derivatives; Manufacture thereof from solutions of cellulose in acids, bases or salts from cuprammonium solutions
    • D—TEXTILES; PAPER
    • D01—NATURAL OR MAN-MADE THREADS OR FIBRES; SPINNING
    • D01F—CHEMICAL FEATURES IN THE MANUFACTURE OF ARTIFICIAL FILAMENTS, THREADS, FIBRES, BRISTLES OR RIBBONS; APPARATUS SPECIALLY ADAPTED FOR THE MANUFACTURE OF CARBON FILAMENTS
    • D01F2/00—Monocomponent artificial filaments or the like of cellulose or cellulose derivatives; Manufacture thereof
    • D01F2/06—Monocomponent artificial filaments or the like of cellulose or cellulose derivatives; Manufacture thereof from viscose
    • D—TEXTILES; PAPER
    • D01—NATURAL OR MAN-MADE THREADS OR FIBRES; SPINNING
    • D01F—CHEMICAL FEATURES IN THE MANUFACTURE OF ARTIFICIAL FILAMENTS, THREADS, FIBRES, BRISTLES OR RIBBONS; APPARATUS SPECIALLY ADAPTED FOR THE MANUFACTURE OF CARBON FILAMENTS
    • D01F2/00—Monocomponent artificial filaments or the like of cellulose or cellulose derivatives; Manufacture thereof
    • D01F2/06—Monocomponent artificial filaments or the like of cellulose or cellulose derivatives; Manufacture thereof from viscose
    • D01F2/08—Composition of the spinning solution or the bath
    • D01F2/10—Addition to the spinning solution or spinning bath of substances which exert their effect equally well in either
    • D—TEXTILES; PAPER
    • D01—NATURAL OR MAN-MADE THREADS OR FIBRES; SPINNING
    • D01F—CHEMICAL FEATURES IN THE MANUFACTURE OF ARTIFICIAL FILAMENTS, THREADS, FIBRES, BRISTLES OR RIBBONS; APPARATUS SPECIALLY ADAPTED FOR THE MANUFACTURE OF CARBON FILAMENTS
    • D01F2/00—Monocomponent artificial filaments or the like of cellulose or cellulose derivatives; Manufacture thereof
    • D01F2/06—Monocomponent artificial filaments or the like of cellulose or cellulose derivatives; Manufacture thereof from viscose
    • D01F2/22—Monocomponent artificial filaments or the like of cellulose or cellulose derivatives; Manufacture thereof from viscose by the dry spinning process
    • 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
    • D06P3/00—Special processes of dyeing or printing textiles, or dyeing leather, furs, or solid macromolecular substances in any form, classified according to the material treated
    • D06P3/58—Material containing hydroxyl groups
    • D06P3/60—Natural or regenerated cellulose
    • D06P3/66—Natural or regenerated cellulose using reactive dyes
    • 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
    • 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
    • D06P5/22—Effecting variation of dye affinity on textile material by chemical means that react with the fibre
    • D06P5/225—Aminalization of cellulose; introducing aminogroups into cellulose
    • 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
    • Y10S8/921—Cellulose ester or ether

Definitions

  • the invention relates to aminated cellulosic synthetic fibers, processes for their Manufacture and its use.
  • cellulose regenerated fibers are the same (in the following also referred to as viscose fibers) essentially the cotton fibers.
  • viscose fibers essentially the cotton fibers.
  • At the current state of the art are for dyeing cellulosic natural or Regenerate fiber alkalis, as well as electrolytes necessary to to achieve satisfactory fixation results with reactive dyes.
  • cellulose regenerated fibers will be important that previously without additional process steps in high dye affinity, i.e. salt and alkali free dyeable, modifications were transferred. Fibers modified in this way are similar to their chemical behavior animal fibers such as wool or silk, and can under neutral conditions with anionic dyes, without further Salt or alkali additives are colored.
  • DE-A-1494547 describes a process for producing and Dyeing threads and staple fibers from regenerated cellulose, at which the viscose is spun with an N-vinyl lactam polymer adds.
  • EP-A-0 546 476 describes a method for Production of a modified fiber material and for dyeing it Fiber material with anionic textile dyes, which one Fiber material modified in such a way that it is in aqueous solution with an aliphatic compound containing amino and ester groups impregnated and subjected to heat treatment.
  • the so modified Fiber material can be mixed with water-soluble, anionic dyes, in particular fiber-reactive dyes, from low-electrolyte or completely electrolyte-free and / or low-alkali or completely alkali-free Dyeing liquor can be dyed.
  • water-soluble, anionic dyes in particular fiber-reactive dyes, from low-electrolyte or completely electrolyte-free and / or low-alkali or completely alkali-free Dyeing liquor can be dyed.
  • This object is surprisingly achieved by adding one amine-substituted cellulose derivative to form a viscose mass or alkali cellulose, or by adding to a cellulose solution.
  • N N-diallyl-N-methyl-N-dodecylammonium halide
  • N N-diallyl-N-methyl-N-octylammonium halide
  • N N-diallyl-N-methyl-N-decylammonium halide
  • N N-diallyl-N, N-dimethylammonium halide
  • N N-diallyl-N, N-dimethylammonium chloride.
  • ester group is a sulfato or phosphato group or a C 1 -C 4 alkanoyl group, phenylsulfonyloxy or one on the benzene nucleus by substituents from the group carboxy, C 1 -C 4 alkyl, C 1 - C 4 alkoxy and nitro substituted phenylsulfonyloxy group.
  • Cellulose derivatives are also suitable for those compounds which act as a reactive residue the amino component has an ⁇ -chloro- ⁇ -hydroxy or epoxy substitution exhibit.
  • such parts of the molecule are generally reactive understand that with hydroxyl groups, for example of cellulose, or amino and thiol groups, for example wool and silk, can react and are able to form a covalent chemical bond.
  • a cellulose component for the production of the amine-substituted Cellulose derivatives have become carboxymethyl cellulose, hydroxyethyl cellulose, Hydroxypropyl cellulose, carboxymethyl hydroxyethyl cellulose, Sulfoethyl cellulose, carboxymethyl sulfoethyl cellulose, Hydroxypropylsulfoethyl cellulose, hydroxyethylsulfoethyl cellulose, Methylsulfoethyl cellulose and ethyl sulfoethyl cellulose have been found to be suitable.
  • the process for making the aminated cellulosic synthetic fibers is carried out either by alkaline cellulose digestion (Alkali cellulose), reacted with carbon disulfide, the xanthate in Sodium hydroxide solution dissolves and the viscose spinning solution thus obtained amine-substituted cellulose derivatives or by adding the amine-substituted cellulose derivatives are added directly to the alkali cellulose and then xanthogenized. By subsequent spinning in an acidic spinning bath the modified viscose fibers according to the invention are obtained.
  • the nitrogenous compounds used for the present process are in an aqueous medium or expediently with the aid of emulsifiers incorporated into the viscose spinning mass and show a good with the viscose Compatibility.
  • the amine-substituted cellulose derivative is added in an amount of 1 to 20%, preferably 1 to 12 wt .-%, based on the Cellulose content of the dope before precipitation and shaping.
  • the expert current process for producing cellulosic fibers from solution such as the cupro process, the lyocell process and the Process on low substituted cellulose ethers, so produced Cellulose dissolved in a suitable organic solvent with which amine-substituted cellulose derivative added and directly from the solution to fibers spun.
  • the best thing to do is to meter in immediately before spinning, where the interference and homogeneous distribution by known mixing systems can be done with the help of static or dynamic mixing systems.
  • the Dosing can also be done in any preliminary stage with the Spinning mass production take place.
  • the aminated celluloses used as additives have degrees of polymerization between 300 and 1000 anhydroglucose units and viscosities from 300 to 1500 mPas.
  • the degree of polymerization should not be less than 300 because otherwise there is a risk that the prefabricated aminated cellulose after the spinning is washed out of the fiber.
  • the prefabricated ones used to manufacture the modified viscose Cellulose derivatives can, due to their solubility in water or in aqueous alkali solution, stir well into the spinning mass.
  • the filterability of the viscose shows no deterioration in comparison with additive free samples, so that no clogging of the in the course of the spinning process Spinneret can be observed.
  • the deformation of the viscose is done according to usual and known methods, such as. B. with spinnerets, one subsequent precipitating bath and, if appropriate, further post-treatment baths.
  • the present invention also relates to a method for the production a colored or printed textile material made from regenerated cellulose fibers, characterized in that a viscose or alkali cellulose amine-substituted cellulose derivative and after the viscose spinning process Fibers spinning, or by making said cellulose derivative from a cellulose solution adds and spins fibers from the solution, the fibers into a fabric or Knitted fabrics processed and this with one or more reactive dyes in Absence of additional electrolyte salt or alkali colors or prints.
  • the textile modified fiber material used in the invention Dyeing process can be used in all processing states, so as Yarn, flake, sliver and piece goods (fabric) are available.
  • the modified textile fiber materials are dyed according to the invention analogous to known dyeing methods and printing processes for dyeing and printing of fiber materials with water-soluble textile dyes and under Application of the temperature ranges known for this and usual amounts of dye, but with the exception that for the dye baths, Block process, printing pastes and ink jet formulations an addition of alkaline compounds, as they are usually used to fix fiber-reactive dyes are used, is not necessary and also on usual Additions to electrolyte salts can be dispensed with. It is therefore one pH between 4.5 and 8.5 and, when using commercially available Reactive dyes, in the presence of an electrolyte salt content of 0.01 to 0.5% by weight, based on the coloring solution, colored or printed. Without that Amination of the cellulose fibers according to the invention would be this electrolyte content too small for a successful dyeing process by a factor of 20 to 1000.
  • Dyeing processes which can be used according to the invention are, for example, the various exhaust processes, such as dyeing on the jigger and on the reel runner or dyeing from a long and short liquor, dyeing in jet dyeing machines, dyeing by padding-cold dwelling or padding -Hot steam fixing process.
  • the dyeing methods which can be used according to the invention also include the printing techniques, including ink-jet printing and transfer printing.
  • the dyes that are used to dye the modified cellulose are generally anionic in nature.
  • the fiber-reactive ones are particularly suitable Textile dyes containing hydroxyl groups, for example cellulose, or Amino and thiol groups, for example wool and silk, from synthetic polymers, such as polyamides, or also modified polymers, just the aminated celluloses, can react and a covalent bond able to enter.
  • a fiber-reactive component on textile dyes especially the sulfatoethylsulfonyl, vinylsulfonyl, chlorotriazinyl, Fluorotriazinyl, as well as combinations of these "anchor systems" called. Unless otherwise stated, these are in the examples below parts listed parts by weight.
  • a hydroxyethyl cellulose modified with N- (2-sulfatoethyl) piperazine (viscosity 925 mPas, DP approx.) Is placed in an industrial spinning viscose with a cellulose content of 8.9%, an alkali content of 5% and a viscosity of 38 falling ball seconds at 30 ° C. 700) stirred in.
  • the procedure is as follows: 16.2 parts of the modified hydroxyethyl cellulose are pasted with 49 parts of water and mixed with 436 parts of spin viscose. This premix is stirred into 2522 parts of spin viscose.
  • the spinning mass is spun into fibers using a customary viscose spinning process in a sulfuric acid, sodium and zinc sulfate-containing bath, stretched in acidic baths, cut, washed, prepared and dried. 10 parts of these dry viscose fibers are then mixed with 100 parts of water in a dyeing apparatus. The mixture is heated to 60 ° C. and a total of 0.1 part of a 50% electrolyte-containing (predominantly sodium-containing) dye powder of the formula known from published patent application 19 43 904 is metered in. over a period of 30 minutes. After a run-on time of 5 minutes, the remaining liquor is drained off and the material is washed out and dried using standard methods. A deep red color with very good fastness properties is obtained.
  • a spun viscose as described in Example 1 is a cellulose modified in accordance with the information in Example 1 of US Pat. No. 4,464,523 with a nitrogen content of 2.9%, a viscosity of 825 mPas (2% solution in water) and a DP -Value of approx. 700 mixed in.
  • the procedure is as described in Example 1 of the present application.
  • the spinning mass is spun into fibers using a customary viscose spinning process in a sulfuric acid, sodium and zinc sulfate-containing bath, stretched in acidic baths, cut, washed, prepared and dried. After weaving, a textile viscose fabric is obtained which can be further processed directly in a dyeing process using the block method.
  • an aqueous dye solution containing 20 parts of the dye of the formula known from EP-A-0 158 233, Example 1, and contains 3 parts of a commercially available nonionic wetting agent dissolved, applied to the fabric at 25 ° C. by means of a padder with a liquor absorption of 80%, based on the weight of the fabric.
  • the fabric padded with the dye solution is wound onto a dock, wrapped in a plastic sheet, left to stand at 40 to 50 ° C. for 4 hours and then with cold and hot water, which may or may not contain a commercial surfactant, and then again with cold water, if necessary rinsed and dried.
  • a strong, uniformly colored yellow coloration is obtained which has good general fastness properties, in particular good fastness to rubbing and light.
  • Example 1 A spinning viscose as described in Example 1 is used accordingly the details of Example 28 of published patent application DE 41 25 752 A1 modified potato starch stirred in. The procedure is the same Information in Example 1 of the present application.
  • a fiber which can be dyed using a conventional pull-out method.
  • 20 parts of the pretreated viscose fiber are treated in a dyeing machine with 200 parts of an aqueous liquor which, based on the weight of the dry goods, contains 1.5% of the reactive dye of the formula known from EP-A-0 061 151, example 4, in a commercially available form and composition.
  • the fiber is dyed with this liquor at 80 ° C. for 30 minutes.
  • the dyeing thus produced is further processed by rinsing and soaping in the customary manner. The result is a lively orange color with the good fastness properties customary for reactive dyes.
  • Example 1 A spinning viscose as described in Example 1 is used accordingly modified the details of Example 2 of DE-A-1 593 657 Hydroxyethylcellulose stirred in. The procedure is the same Information in Example 1 of the present application.
  • a fiber made of modified viscose is obtained, which can be dyed in a pull-out process without salt and alkali additives.
  • 30 parts of viscose yarn are wound on a cross-wound bobbin and the yarn is treated in a yarn dyeing machine, the 450 parts (based on the weight of the goods) of a liquor, the 0.6 parts, based on the initial weight of the goods, of an electrolyte-containing dye (predominantly containing sodium chloride) general Formula, known from DE-A-28 40 380, example 1, contains and heats to 80 ° C., the liquor being pumped alternately from the inside to the outside and from the outside to the inside. After 60 minutes at this temperature, the liquor is drained off, rinsed and washed according to the usual conditions, the dyeing obtained. An irrespective yellow colored fiber with generally good fastness properties for reactive dyes is obtained.

Landscapes

  • Engineering & Computer Science (AREA)
  • Textile Engineering (AREA)
  • Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Artificial Filaments (AREA)
  • Polysaccharides And Polysaccharide Derivatives (AREA)
  • Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
  • Coloring (AREA)

Claims (14)

  1. Fibres synthétiques cellulosiques aminées, fabriquées par addition, à une masse de viscose ou de cellulose alcaline, d'un dérivé cellulosique substitué par une amine et filage des fibres selon le procédé de filage de la viscose, ou par addition dudit dérivé cellulosique à une solution de cellulose et filage des fibres au départ de la solution, caractérisé en ce que les dérivés cellulosiques substitués par des amines sont des polymères d'amines oléfiniques insaturées avec de la cellulose ou des composants cellulosiques ; ou bien, que lesdits dérivés cellulosiques substitués par des amines sont des produits de réaction entre la cellulose ou des composants cellulosiques et des amines de formule générale (1a) ou (1b)
    Figure 00320001
    Figure 00320002
    dans laquelle
    Y
    est un radical ester
    A et N
    forment ensemble, avec 1 ou 2 radicaux alkyle de 1 à 4 atomes de carbone, le radical bivalent d'un hétérocycle dans lequel
    A
    est un atome d'oxygène ou un radical de formule générale (a), (b) ou (c)
    Figure 00330001
    dans laquelle
    R
    signifie un atome d'hydrogène, ou un radical amino ou un radical alkyle de 1 à 6 atomes de carbone, qui peut être substitué par 1 ou 2 substituants des radicaux amino, sulfo, hydroxy, sulfato, phosphato ou carboxy, ou un radical alkyle de 3 à 8 atomes de carbone interrompu par 1 ou 2 radicaux de formules -O- et -NH- ou une combinaison de ceux- ci et peut être substitué par un radical amino, sulfo, hydroxy, sulfato ou carboxy,
    R1
    est un hydrogène, un méthyle ou un éthyle,
    R2
    est un hydrogène, un méthyle ou un éthyle, et
    Z(-)
    signifie un anion ;
    B
    est un radical amino de formule H2N- ou un radical amino ou ammonium de formule générale (d) ou (e)
    Figure 00330002
    dans laquelle
    R1, R2 et Z(-)
    ont l'une des significations ci-dessus,
    R3
    est un méthyle ou un éthyle, et
    R4
    signifie un hydrogène, un méthyle ou un éthyle ;
    p
    est égal à 1 ou 2 ;
    l'alkylène
    est un radical alkylène à chaíne linéaire ou ramifiée de 2 à 6 atomes de carbone, qui peut être substitué par 1 ou 2 radicaux hydroxy, ou est un radical alkylène de 3 à 8 atomes de carbone à chaíne linéaire ou ramifiée interrompue par 1 ou 2 radicaux de formules -O- et -NH- ou une combinaison des deux ;
    alk
    est un radical alkylène à chaíne linéaire ou ramifiée de 2 à 6 atomes de carbone, ou un radical alkylène à chaíne linéaire ou ramifiée de 3 à 8 atomes de carbone interrompue par 1 ou 2 radicaux de formules -O- et -NH- ou une combinaison des deux, et est de préférence un radical alkylène à chaíne linéaire ou ramifiée de 2 à 6 atomes de carbone ;
    m
    est égal à 1 ou 2 ;
    n
    a une valeur de 1 à 4 ;
    les radicaux amino, hydroxy et ester peuvent être liés à un carbone primaire, secondaire ou tertiaire du radical alkylène.
  2. Fibres synthétiques cellulosiques aminées selon la revendication 1, caractérisées en ce que les polymères de A) et B) de dérivés cellulosiques substitués par des amines sont dans une proportion (A) : (B) de (95 à 20) : (5 à 80), avec
    A) des monomères ou des mélanges de monomères des groupes :
    a) N-vinylimidazole, substitués sur l'hétérocycle par un maximum de trois radicaux alkyle C1-C12 et pouvant être présents sous forme de N quaternaire ou sous forme de sel;
    b) N-vinyllactame avec 5 à 8 maillons, pouvant être substitués sur le cycle par un maximum de trois radicaux alkyle C1-C12;
    c) dialkylaminoester de l'acide acrylique ou méthacrylique avec au total jusqu'à 30 atomes de carbone dans le radical dialkylaminoalkyle, qui peut être présent sous forme de N quaternaire ou de sel;
    d) amide de l'acide N-(dialkylaminoalkyl)acrylique ou -méthacrylique, avec au total jusqu'à 30 atomes de carbone dans le radical dialkylaminoalkyle, qui peut être présent sous forme de N quaternaire ou de sel; et
    e) diallyle-C1-C12-alkylamine ou ses sels, ou composés de diallyle-di(C1-C12-alkyle)-ammonium; d'autres comonomères pour (A) pouvant encore être
    f) des acides carboxyliques C3-C10 monoéthyléniques insaturés et leurs sels de métaux alcalins, de métaux alcalinoterreux ou d'ammonium,
    g) des esters carboxyliques C3-C10 monoéthyléniques insaturés, et
    h) des composés contenant dans leur molécule au moins deux doubles liaisons éthyléniques insaturées non conjuguées, et
    B) des monosaccharides, oligosaccharides, polysaccharides, des polysaccharides traités thermiquement ou mécaniquement, décomposés par oxydation, hydrolyse ou processus enzymatique, des mono-, oligo- ou polysaccharides chimiquement modifiés ou des mélanges des composés (B) ci-dessus.
  3. Fibres synthétiques cellulosiques aminées selon la revendication 2, caractérisées en ce que, dans lesdits polymères, les monomères (A) sont soit les composés individuels (a), (c), (d) et (e) seuls, soit des mélanges de 5 à 95% en poids d'un composé (b) et de 95 à 5% en poids d'un ou plusieurs des composés (a), (c), (d), (e), (f), (g) et (h) ; (h) étant présent en une quantité maximale de 5% en poids, ramenée à la quantité totale de tous les monomères (A).
  4. Fibres synthétiques cellulosiques aminées selon la revendication 1, caractérisées en ce que les dérivés cellulosiques substitués par des amines sont des polymères d'halogénures de N,N-diallyle-N,N-di(C1-C12)-alkyle-ammonium et de cellulose ou de dérivés cellulosiques.
  5. Fibres synthétiques cellulosiques aminées selon la revendication 4, caractérisées en ce que l'halogénure de N,N-diallyl-N,N-di(C1-C12)alkylammonium est un halogénure de N,N-diallyl-N-méthyl-N-dodécylammonium, un halogénure de N,N-diallyl-N-méthyl-N-octylammonium, un halogénure de N,N-diallyl-N-méthyl-N-décylammonium, un halogénure de N,N-diallyl-N,N-diméthylammonium, et en particulier le chlorure de N,N-diallyl-N,N-diméthylammonium.
  6. Fibres synthétiques cellulosiques aminées selon la revendication 1, caractérisées en ce que le radical ester Y est un radical sulfato ou phosphato ou un radical alcanoyle C1-C4, un noyau phénylsulfonyloxy ou un radical phénylsulfonyloxy substitué sur le noyau de benzène par des substituants du groupe carboxy, alkyle C1-C4, alkoxy C1-C4 et nitro.
  7. Fibres synthétiques cellulosiques aminées selon la revendication 1, caractérisées en ce que l'amine est un composé du groupe N-(β-sulfatoéthyl)piperazine, sulfate de N-(2-sulfatoéthyl)piperazine, N-[β-(β'-sulfatoéthoxy)éthyl]piperazine, N-(γ-sulfato-β-hydroxypropyl)pipéridine, N-(γ-sulfato-β-hydroxypropyl)pyrrolidine, N-(β-sulfatoéthyl)pipéridine, 2-sulfato-3-hydroxy-1-aminopropane, 3-sulfato-2-hydroxy-1-aminopropane, 1-sulfato-3-hydroxy-2-aminopropane, 3-hydroxy-1-sulfato-2-aminopropane, 2,3-disulfato-1-aminopropane, 1,3-disulfato-2-aminopropane ou un dérivé de ces composés avec un radical phosphato, C1-C4-alcanoyle, phénylsulfonyloxy ou, à la place du groupe sulfato, un radical phénylsulfonyloxy substitué sur le noyau benzénique par des substituants du groupe carboxy, C1-C4-alkyle, C1-C4-alcoxy et nitro.
  8. Fibres synthétiques cellulosiques aminées selon la revendication 1, caractérisées en ce que les amines présentent une partie de molécule réactive, capable de réagir avec des radicaux hydroxy, en particulier une substitution α-chloro-β-hydroxy ou époxy.
  9. Fibres synthétiques cellulosiques aminées selon l'une au moins des revendications 1 à 8, caractérisées en ce que les composés cellulosiques utilisés pour la préparation des dérivés cellulosiques substitués par des amines sont la carboxyméthylcellulose, l'hydroxyéthylcellulose, l'hydroxypropylcellulose, la carboxyméthylhydroxyéthylcellulose, la sulfoéthylcellulose, la carboxyméthylsulfoéthylcellulose, l'hydroxypropylsulfoéthylcellulose, l'hydroxyéthylsulfoéthylcellulose, la méthylsulfoéthylcellulose ou l'éthylsulfoéthylcellulose.
  10. Fibres synthétiques cellulosiques aminées selon l'une au moins des revendications 1 à 9, caractérisées en ce que les dérivés cellulosiques substitués par des amines présentent des degrés de polymérisation entre 300 et 1000 unités de glucose anhydre et des viscosités de 300 à 1500 mPa.s.
  11. Fibres synthétiques cellulosiques aminées selon l'une au moins des revendications 1 à 10, caractérisées en ce que les fibres cellulosiques régénérées sont filées selon le procédé au cuivre ou lyocell.
  12. Fibres synthétiques cellulosiques aminées selon l'une au moins des revendications 1 à 11, caractérisées en ce que le dérivé cellulosique substitué par une amine est ajouté à une concentration de 1 à 20% en poids, et en particulier 1 à 12% en poids, ramenée à la teneur en cellulose de la masse à filer.
  13. Procédé pour la préparation d'un matériau textile coloré ou imprimé en fibres synthétiques cellulosiques selon la revendication 1, caractérisé en ce que l'on ajoute à une masse de viscose ou de cellulose alcaline un dérivé cellulosique substitué par une amine et que l'on file les fibres par le procédé de filage de la viscose, ou que l'on ajoute ledit dérivé cellulosique à une solution de cellulose et que l'on file les fibres au départ de la solution, les fibres étant ensuite travaillées en tissu ou en tricot, ce tissu ou tricot étant enfin coloré ou imprimé au moyen d'un ou plusieurs colorants réactifs en l'absence d'électrolyte ou alcali additionnels.
  14. Procédé selon la revendication 13, caractérisé en ce que le matériau textile est coloré ou imprimé à un pH entre 4,5 et 8,5.
EP95100299A 1994-01-29 1995-01-11 Fibres synthétiques cellulosiques aminées Expired - Lifetime EP0665311B1 (fr)

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
DE4402711 1994-01-29
DE19944402711 DE4402711A1 (de) 1994-01-29 1994-01-29 Aminierte Cellulose-Regeneratfasern, Verfahren zu ihrer Herstellung und ihre Verwendung
DE19944422758 DE4422758A1 (de) 1994-06-29 1994-06-29 Aminierte Cellulose-Regeneratfasern
DE4422758 1994-06-29

Publications (2)

Publication Number Publication Date
EP0665311A1 EP0665311A1 (fr) 1995-08-02
EP0665311B1 true EP0665311B1 (fr) 1998-12-09

Family

ID=25933390

Family Applications (1)

Application Number Title Priority Date Filing Date
EP95100299A Expired - Lifetime EP0665311B1 (fr) 1994-01-29 1995-01-11 Fibres synthétiques cellulosiques aminées

Country Status (11)

Country Link
US (2) US5684141A (fr)
EP (1) EP0665311B1 (fr)
JP (1) JPH07300719A (fr)
KR (1) KR950032755A (fr)
CN (1) CN1109925A (fr)
AT (1) ATE174388T1 (fr)
CA (1) CA2141267A1 (fr)
DE (1) DE59504452D1 (fr)
DK (1) DK0665311T3 (fr)
ES (1) ES2126794T3 (fr)
FI (1) FI113281B (fr)

Families Citing this family (17)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE4435385A1 (de) * 1994-10-04 1996-04-11 Hoechst Ag Verfahren zum Färben von modifizierten Viskosefasern mit Säure- oder Direktfarbstoffen
DE4446540A1 (de) * 1994-12-24 1996-06-27 Hoechst Ag Verfahren zur Herstellung von wasserlöslichen Aminoalkylderivaten von Polysacchariden
DE19549408A1 (de) * 1995-05-24 1997-01-09 Hoechst Ag Mit hochsubstituierter Stärke aminierte Celluloseregeneratfasern
DE19519024A1 (de) * 1995-05-24 1996-11-28 Hoechst Ag Verfahren zur Spinnfärbung mit Farbsalzen
AT402740B (de) * 1995-10-06 1997-08-25 Chemiefaser Lenzing Ag Cellulosefaser
DE19605578C2 (de) 1996-02-15 2001-03-29 Dystar Textilfarben Gmbh & Co Verfahren zur Herstellung eines anionischen Textilfarbstoffen bedruckten textilen Materials
CN1306081C (zh) * 2005-07-26 2007-03-21 高明宝 一种抗菌除螨纤维制品及制造方法
JP5490724B2 (ja) * 2008-02-08 2014-05-14 リスト ホールディング アーゲー 成形物の製造方法及び装置
US9221963B2 (en) * 2008-11-27 2015-12-29 Speciality Fibres And Materials Ltd. Absorbent material
WO2010105357A1 (fr) * 2009-03-20 2010-09-23 Fpinnovations Matériaux de cellulose dotés de nouvelles propriétés
US8399590B2 (en) * 2009-10-07 2013-03-19 Akzo Nobel Chemicals International B.V. Superhydrophilic amphiphilic copolymers and processes for making the same
US11173106B2 (en) * 2009-10-07 2021-11-16 Johnson & Johnson Consumer Inc. Compositions comprising a superhydrophilic amphiphilic copolymer and a micellar thickener
US8258250B2 (en) 2009-10-07 2012-09-04 Johnson & Johnson Consumer Companies, Inc. Compositions comprising superhydrophilic amphiphilic copolymers and methods of use thereof
EP2556186B1 (fr) 2010-04-08 2017-01-04 LIST Holding AG Procédé de production d'un produit
JP5356582B2 (ja) * 2011-12-28 2013-12-04 花王株式会社 ポリエステル樹脂組成物
CN104746161A (zh) * 2013-12-31 2015-07-01 上海水星家用纺织品股份有限公司 一种药物纤维的生产工艺以及药物家纺纤维
CN108193310B (zh) * 2017-12-30 2020-11-13 安徽宏祥丝绸织造有限公司 一种弹力双乔用耐热氨纶纤维的制备方法

Family Cites Families (16)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
BE638428A (fr) * 1962-10-09
NL6506343A (fr) * 1964-06-01 1965-12-02
US3472840A (en) * 1965-09-14 1969-10-14 Union Carbide Corp Quaternary nitrogen-containing cellulose ethers
GB1243194A (en) * 1967-12-13 1971-08-18 Courtaulds Ltd The manufacture of more dyeable regenerated cellulose filaments
FR1581593A (fr) * 1968-06-25 1969-09-19
CH508060A (de) * 1968-10-01 1971-05-31 Ciba Geigy Ag Verfahren zur Herstellung von modifizierten Viskosefasern
US4464523A (en) * 1983-05-16 1984-08-07 National Starch And Chemical Corporation Process for the preparation of graft copolymers of cellulose derivatives and diallyl, dialkyl ammonium halides
SE452448B (sv) * 1985-02-04 1987-11-30 Hyco Hydraulic Ab Lyftanordning for lyftning av fordon
DE3709766A1 (de) * 1987-03-25 1988-10-06 Hoechst Ag Verfahren zum alkali-freien faerben mit reaktivfarbstoffen
DE3831464A1 (de) * 1988-09-16 1990-03-29 Hoechst Ag Verfahren zum alkali-freien faerben und bedrucken von cellulosefasern
TW201803B (fr) * 1991-04-15 1993-03-11 Hoechst Ag
TW223134B (fr) * 1991-05-11 1994-05-01 Hoechst Ag
DE4125752A1 (de) * 1991-08-03 1993-02-04 Basf Ag Polymerisate aus ethylenisch ungesaettigten, n-haltigen verbindungen, polymerisiert in gegenwart von monosacchariden, oligosacchariden, polysacchariden oder deren derivaten
TW211595B (fr) * 1991-12-07 1993-08-21 Hoechst Ag
JP3234270B2 (ja) * 1992-03-19 2001-12-04 富士通株式会社 面放電型プラズマディスプレイパネル
DE4435385A1 (de) * 1994-10-04 1996-04-11 Hoechst Ag Verfahren zum Färben von modifizierten Viskosefasern mit Säure- oder Direktfarbstoffen

Also Published As

Publication number Publication date
FI950343A (fi) 1995-07-30
EP0665311A1 (fr) 1995-08-02
DE59504452D1 (de) 1999-01-21
JPH07300719A (ja) 1995-11-14
ATE174388T1 (de) 1998-12-15
US5684141A (en) 1997-11-04
FI950343A0 (fi) 1995-01-26
ES2126794T3 (es) 1999-04-01
KR950032755A (ko) 1995-12-22
CA2141267A1 (fr) 1995-07-30
US5865858A (en) 1999-02-02
CN1109925A (zh) 1995-10-11
DK0665311T3 (da) 1999-08-16
FI113281B (fi) 2004-03-31

Similar Documents

Publication Publication Date Title
EP0665311B1 (fr) Fibres synthétiques cellulosiques aminées
DE69223305T2 (de) Behandlung von cellulosischen Fasern zur Verringerung ihrer Fibrillierneigung
DE19519025C1 (de) Hochgradig mit Alkylsulfonsäureresten veretherte Stärke
EP0692559A1 (fr) Fibres synthétiques cellulosiques modifiées par des composés aminés polymères
EP0828868B1 (fr) Amination de cellulose regeneree avec des amidons a haut degre de substitution et utilisation des fibres ainsi modifiees
EP0683251B1 (fr) Amination de fibres synthétiques cellulosiques
AT409144B (de) Verfahren zur behandlung von cellulosefasern und von gebilden aus diesen fasern
EP0703305A1 (fr) Procédé pour la fabrication de cellulose régénérée aminée
EP0692558A1 (fr) Procédé pour la fabrication de fibres aminées de cellulose régénerée
EP0705924A2 (fr) Procédé de teinture de fibres de viscose modifiées, avec des colorants acides ou directs
DE69600639T2 (de) Anthrachinonreaktivfarbstoffzusammensetzungen und diese verwendende Färbe- oder Druckverfahren
DE4402711A1 (de) Aminierte Cellulose-Regeneratfasern, Verfahren zu ihrer Herstellung und ihre Verwendung
DE4422758A1 (de) Aminierte Cellulose-Regeneratfasern
DE69226834T2 (de) Reaktivfarbstoffmischungen und deren Verwendung
DE19519023C1 (de) Mit Aminogruppen hochsubstituierte Stärken
DE3141082A1 (de) Verfahren zum kontinuierlichen faerben von fasergut von aus organischen loesemitteln versponnenen acrylnitril-polymerisaten im gelzustand
DE4421740A1 (de) Aminierung von Regeneratcellulose
CH687355B5 (de) Verfahren zum Färben von Cellulose-Textilmaterial.
AT205654B (de) Verfahren zur Herstellung gefärbter Gebilde, insbesondere Fasern und Folien, aus Viskose
DE4417211A1 (de) Aminierung von Regeneratcellulose
DE2023179C (de) Verfahren zum Farben und Bedrucken von Textilfasern
DE29520890U1 (de) Hochsubstituierte Stärken und mit hochsubstituierten Stärken aminierte Regeneratcellulose
DE2438543B2 (de) Verfahren zur Herstellung gefärbter Fäden aus vollaromatischen Polyamiden
DE2023179A1 (de) Verfahren zum Faerben und Bedrucken von Textilfasern
DE2442553C2 (de) Farbstoffpräparationen zur Herstellung tiefer Gelbtöne mit Reaktivfarbstoffen, deren Herstellung und deren Verwendung

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

AK Designated contracting states

Kind code of ref document: A1

Designated state(s): AT BE CH DE DK ES FR GB IT LI SE

17P Request for examination filed

Effective date: 19960202

17Q First examination report despatched

Effective date: 19970722

RAP1 Party data changed (applicant data changed or rights of an application transferred)

Owner name: DYSTAR TEXTILFARBEN GMBH & CO. DEUTSCHLAND KG

GRAG Despatch of communication of intention to grant

Free format text: ORIGINAL CODE: EPIDOS AGRA

GRAG Despatch of communication of intention to grant

Free format text: ORIGINAL CODE: EPIDOS AGRA

GRAH Despatch of communication of intention to grant a patent

Free format text: ORIGINAL CODE: EPIDOS IGRA

GRAH Despatch of communication of intention to grant a patent

Free format text: ORIGINAL CODE: EPIDOS IGRA

GRAA (expected) grant

Free format text: ORIGINAL CODE: 0009210

AK Designated contracting states

Kind code of ref document: B1

Designated state(s): AT BE CH DE DK ES FR GB IT LI SE

REF Corresponds to:

Ref document number: 174388

Country of ref document: AT

Date of ref document: 19981215

Kind code of ref document: T

REG Reference to a national code

Ref country code: CH

Ref legal event code: EP

REF Corresponds to:

Ref document number: 59504452

Country of ref document: DE

Date of ref document: 19990121

GBT Gb: translation of ep patent filed (gb section 77(6)(a)/1977)

Effective date: 19990112

ET Fr: translation filed
ITF It: translation for a ep patent filed
REG Reference to a national code

Ref country code: ES

Ref legal event code: FG2A

Ref document number: 2126794

Country of ref document: ES

Kind code of ref document: T3

REG Reference to a national code

Ref country code: DK

Ref legal event code: T3

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

26N No opposition filed
PGFP Annual fee paid to national office [announced via postgrant information from national office to epo]

Ref country code: DK

Payment date: 20011221

Year of fee payment: 8

PGFP Annual fee paid to national office [announced via postgrant information from national office to epo]

Ref country code: CH

Payment date: 20011224

Year of fee payment: 8

REG Reference to a national code

Ref country code: GB

Ref legal event code: IF02

PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: LI

Free format text: LAPSE BECAUSE OF NON-PAYMENT OF DUE FEES

Effective date: 20030131

Ref country code: DK

Free format text: LAPSE BECAUSE OF NON-PAYMENT OF DUE FEES

Effective date: 20030131

Ref country code: CH

Free format text: LAPSE BECAUSE OF NON-PAYMENT OF DUE FEES

Effective date: 20030131

REG Reference to a national code

Ref country code: DK

Ref legal event code: EBP

REG Reference to a national code

Ref country code: CH

Ref legal event code: PL

PGFP Annual fee paid to national office [announced via postgrant information from national office to epo]

Ref country code: GB

Payment date: 20051222

Year of fee payment: 12

PGFP Annual fee paid to national office [announced via postgrant information from national office to epo]

Ref country code: ES

Payment date: 20060113

Year of fee payment: 12

PGFP Annual fee paid to national office [announced via postgrant information from national office to epo]

Ref country code: SE

Payment date: 20060120

Year of fee payment: 12

Ref country code: FR

Payment date: 20060120

Year of fee payment: 12

Ref country code: AT

Payment date: 20060120

Year of fee payment: 12

PGFP Annual fee paid to national office [announced via postgrant information from national office to epo]

Ref country code: DE

Payment date: 20060123

Year of fee payment: 12

Ref country code: BE

Payment date: 20060123

Year of fee payment: 12

PGFP Annual fee paid to national office [announced via postgrant information from national office to epo]

Ref country code: IT

Payment date: 20060131

Year of fee payment: 12

PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: SE

Free format text: LAPSE BECAUSE OF NON-PAYMENT OF DUE FEES

Effective date: 20070112

PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: DE

Free format text: LAPSE BECAUSE OF NON-PAYMENT OF DUE FEES

Effective date: 20070801

EUG Se: european patent has lapsed
GBPC Gb: european patent ceased through non-payment of renewal fee

Effective date: 20070111

REG Reference to a national code

Ref country code: FR

Ref legal event code: ST

Effective date: 20070930

PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: GB

Free format text: LAPSE BECAUSE OF NON-PAYMENT OF DUE FEES

Effective date: 20070111

Ref country code: AT

Free format text: LAPSE BECAUSE OF NON-PAYMENT OF DUE FEES

Effective date: 20070111

BERE Be: lapsed

Owner name: *DYSTAR TEXTILFARBEN G.M.B.H. & CO. DEUTSCHLAND K.

Effective date: 20070131

PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: BE

Free format text: LAPSE BECAUSE OF NON-PAYMENT OF DUE FEES

Effective date: 20070131

REG Reference to a national code

Ref country code: ES

Ref legal event code: FD2A

Effective date: 20070112

PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: FR

Free format text: LAPSE BECAUSE OF NON-PAYMENT OF DUE FEES

Effective date: 20070131

PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: ES

Free format text: LAPSE BECAUSE OF NON-PAYMENT OF DUE FEES

Effective date: 20070112

PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: IT

Free format text: LAPSE BECAUSE OF NON-PAYMENT OF DUE FEES

Effective date: 20070111