EP0904444A1 - Procede de traitement de fibres de cellulose et de structures constituees de ces fibres - Google Patents

Procede de traitement de fibres de cellulose et de structures constituees de ces fibres

Info

Publication number
EP0904444A1
EP0904444A1 EP97926908A EP97926908A EP0904444A1 EP 0904444 A1 EP0904444 A1 EP 0904444A1 EP 97926908 A EP97926908 A EP 97926908A EP 97926908 A EP97926908 A EP 97926908A EP 0904444 A1 EP0904444 A1 EP 0904444A1
Authority
EP
European Patent Office
Prior art keywords
fibers
textile
carbon atoms
lyocell
general formula
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.)
Granted
Application number
EP97926908A
Other languages
German (de)
English (en)
Other versions
EP0904444B1 (fr
Inventor
Markus Eibl
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.)
Lenzing AG
Original Assignee
Lenzing AG
Chemiefaser Lenzing AG
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
Application filed by Lenzing AG, Chemiefaser Lenzing AG filed Critical Lenzing AG
Publication of EP0904444A1 publication Critical patent/EP0904444A1/fr
Application granted granted Critical
Publication of EP0904444B1 publication Critical patent/EP0904444B1/fr
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

Links

Classifications

    • DTEXTILES; PAPER
    • D01NATURAL OR MAN-MADE THREADS OR FIBRES; SPINNING
    • D01FCHEMICAL FEATURES IN THE MANUFACTURE OF ARTIFICIAL FILAMENTS, THREADS, FIBRES, BRISTLES OR RIBBONS; APPARATUS SPECIALLY ADAPTED FOR THE MANUFACTURE OF CARBON FILAMENTS
    • D01F2/00Monocomponent artificial filaments or the like of cellulose or cellulose derivatives; Manufacture thereof
    • DTEXTILES; PAPER
    • D06TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06MTREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M13/00Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment
    • D06M13/322Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with compounds containing nitrogen
    • D06M13/35Heterocyclic compounds
    • D06M13/355Heterocyclic compounds having six-membered heterocyclic rings
    • D06M13/358Triazines
    • DTEXTILES; PAPER
    • D06TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06PDYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
    • D06P1/00General 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
    • D06P1/0004General aspects of dyeing
    • DTEXTILES; PAPER
    • D06TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06PDYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
    • D06P1/00General 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
    • D06P1/44General 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
    • D06P1/64General 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
    • D06P1/642Compounds containing nitrogen
    • D06P1/6426Heterocyclic compounds
    • DTEXTILES; PAPER
    • D06TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06PDYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
    • D06P3/00Special processes of dyeing or printing textiles, or dyeing leather, furs, or solid macromolecular substances in any form, classified according to the material treated
    • D06P3/58Material containing hydroxyl groups
    • D06P3/60Natural or regenerated cellulose
    • D06P3/66Natural or regenerated cellulose using reactive dyes

Definitions

  • the invention relates to a process for treatment of cellulosic fibers and structures made from these cellulose fibers, in which method the fibers or the fiber structure are contacted with a textile auxiliary agent in contact 'to impart to the fibers of improved properties.
  • the invention further relates to new fiber structures, such as yarns and textile surfaces, which are obtainable by this process.
  • a tertiary amine oxide in particular N-methylmorpholine-N-oxide (NMMO)
  • NMMO N-methylmorpholine-N-oxide
  • WO 92/07124 describes a method for producing a fiber with a reduced tendency to fibrillation, according to which the freshly spun, that is to say not yet dried, fiber is treated with a cationic polymer.
  • a polymer with imidazole and azetidine groups is mentioned as such a polymer.
  • treatment with an emulsifiable polymer e.g. Polyethylene or polyvinyl acetate, or crosslinking with glyoxal.
  • EP-A-0 538 977 and WO 94/09191 describe a process of the type mentioned at the outset in which fibers of the Lyocell genus are brought into contact with a textile auxiliary in order to reduce the tendency to fibrillation.
  • WO 94/24343 describes a process for the production of cellulose fibers with reduced tendency to fibrillation, in which Process spun a solution of cellulose in a tertiary amine oxide into fibers and the freshly spun fibers are brought into contact with a textile auxiliary which carries at least two reactive groups and are washed with an aqueous buffer, glyoxal not being used as the textile auxiliary. According to this previously known method, the freshly spun fibers are best brought into contact with the textile auxiliary in an alkaline environment.
  • fiber structures made from fibers of the Lyocell genus can be crosslinked with methylol compounds in order to produce washable fabrics and knitted fabrics.
  • methylol compounds it has been shown that it is not possible to prevent the formation of abrasive edges during the coloring when using these compounds. For this, the crosslinking would have to take place before the dyeing or at least during the dyeing.
  • methylol compounds and the other classic finishing agents are hardly suitable for this.
  • Another disadvantage of methylol compounds is the formation of formaldehyde, which leads to stress in the workplace.
  • the invention has for its object to provide a process for the treatment of cellulose fibers of the Lyocell genus and of structures made of these fibers, which can be carried out in a simple manner and which enables the treated fibers to have a reduced tendency to fibrillation or treated fiber structures or fiber structures containing treated fibers have improved abrasion and pilling values.
  • the process according to the invention for the treatment of cellulose fibers, in which the fibers are brought into contact with a textile auxiliary, is characterized in that a compound having the general formula is used as the textile auxiliary
  • X is halogen, alkoxy with 1-4 carbon atoms, amino, alkylamino with 1-4 carbon atoms, hydroxysulfonyl, or 1-nicotinyl; Y the general formula
  • n is the number 1 or 2;
  • R is hydrogen, alkyl of 1-4 carbon atoms or phenyl;
  • R 2 and R3 are hydrogen, hydroxysulfonyl, hydroxyl, halogen, alkyl of 1-4 carbon atoms or carboxyl;
  • A is vinyl or -C-H.B, wherein B is a group which can be split off under alkaline conditions; and
  • Z is Y or X.
  • An expedient embodiment of the method according to the invention is characterized in that fibers of the Lyocell genus are brought into contact with the textile auxiliary used according to the invention in an alkaline environment.
  • Crosslinkers acting in an alkaline environment can be used during reactive dyeing.
  • a preferred embodiment of the method according to the invention is that the compound as a textile auxiliary
  • Further preferred embodiments of the method according to the invention consist in that the fibers are used in the undyed state, or that the treatment is carried out, the fibers being dyed at the same time, or that the fibers are present as fiber structures.
  • the present invention further relates to the use of a compound of the general formula
  • X, Y and Z have the meaning given above, or their alkali metal salt, as textile auxiliaries for the treatment of fibers of the Lyocell genus or for the treatment of structures made of fibers of the Lyocell genus, a yarn or a textile surface being best used as the fiber structure .
  • a woven, knitted or knitted fabric is particularly suitable as a textile surface.
  • the invention further relates to the use of the above compound of general formula (I) to improve the Pilling behavior, to reduce the formation of pills and to improve the chafing behavior of the textile surface.
  • the present invention further relates to fibers of the Lyocell genus which can be obtained by the process according to the invention, or to yarns and fiber structures which contain these fibers.
  • Cellulose fibers of the Lyocell genus were produced in accordance with the process described in EP-A-0 356 419 and WO 93/19230. These fibers were processed into a textile in a known manner. The treatment of the fibers is carried out with the compound of formula (III). This compound is referred to below as "substance I”.
  • the textile is impregnated with a liquor ratio of 1:20 with 6% reactive dye (Remazol Brilliantblau BB or Remazol Schwarz B) in 40 minutes at 40 * c.
  • the dye bath contains 0.3 ml / 1 of an anti-wrinkle (e.g. Biavin 109).
  • 50 g / 1 Na-SO. added in portions.
  • 5 g / l Na_C0 are added and the mixture is heated to 60'C.
  • 0.25 ml / 1 NaOH are added and staining is continued for a further 20 minutes. It is then rinsed warm, brought to pH 5.5 with acetic acid and rinsed cold, boiling and finally cold again.
  • the Textiles with 1 ml / 1 softener Basosoft, Avivan GSA
  • Example 2 This example is analogous to Example 1, except that the following fabric is used instead of the single jersey: 100% Lyocell, 1.7 dtex, twill, weft and chain Nm 50, 150 cm long and 30 cm wide.
  • Example 5 This example is analogous to Example 2, but the following fabric is used instead of the single jersey: 100% Lyocell, 1.7 dtex, twill, weft and chain Nm 50, 150 cm long and 30 cm wide.
  • Example 3 This example is analogous to Example 3, except that the following fabric is used instead of the single jersey: 100% Lyocell, 1.7 dtex, twill, weft and chain Nm 50, 150 cm long and 30 cm wide.
  • the fabrics obtained in Examples 4, 5 and 6 are sewn together and dyed on the laboratory jet (Mathis, 40 mm nozzle, 1 revolution / minute) according to the above dyeing instructions.
  • Example 6 shows clear brightening due to abrasive edges, whereas the fabrics of Examples 4 and 5 are streak-free.
  • the fabrics of Examples 4 and 5 also show significantly better values than the fabric piece of Example 6 with regard to pill formation and whitening.
  • the tissues are treated with 1 ml / 1 plasticizer (Basosoft, Avivan GSA) at 60'C and waxed.
  • 1 ml / 1 plasticizer Basosoft, Avivan GSA
  • a single jersey and socks are knitted from the yarn thus obtained.
  • the tissues are treated with 1 ml / 1 plasticizer (Basosoft, Avivan GSA) at 60'C and waxed. Socks are knitted from the yarn thus obtained.
  • 1 ml / 1 plasticizer Basosoft, Avivan GSA
  • the single jersey from Example 7 and a single jersey made from the same, untreated yarn are dyed together in the laboratory jet (Mathis, nozzle 40 mm, 1 revolution / minute) according to the above dyeing instructions, the fabrics 9a and 9b being obtained.
  • the dyed single jersey 9a shows no streaks or chafing. In contrast, the single jersey 9b abrasive edges and graying are clearly visible.
  • the socks are washed repeatedly at 40 * C. Drying takes place in the tumbler. After 5 washing cycles, the socks made from the yarn of Example 8 are grayed out. The socks made from the yarn of Example 7, on the other hand, have no graying or abrasive edges.
  • the pilling test is carried out in a dry state in accordance with SN 198525.
  • the assessment is carried out visually according to the standard with the help of comparison images.
  • the grade 5 means a low pilling, while the grade 1 means an extreme pilling.
  • “Pill 125”, “Pill 500” and “Pill 2000” means pilling after 125, 500 and 2000 cycles, respectively.
  • a Lyocell fabric dyed with reactive dyes (twill, 1.7 dtex, Nm 50) is impregnated with a liquor on the pad (liquor absorption: 80%), which contains 10 g / 1 crosslinker and 3 ml wetting agent (Leonil SR). Then the fabric is dried at 60 ° C and impregnated again with a liquor (liquor absorption: 80%) which contains 10 g / 1 crosslinking agent (substance I or TAHT), 3 ml wetting agent (Leonil SR), 10 g / 1 plasticizer ( Sandolub NV), 10 g / 1 Na 2 CO 3 and 1 ml / 1 NaOH contains.
  • the fabric is then left to rest sealed in a film at 70 ° C. for 16 hours. Then it is rinsed (cold, warm and finally boiling), mixed with acetic acid and dried at 60'C. The result regarding whitening is shown in Table IV.

Landscapes

  • Engineering & Computer Science (AREA)
  • Textile Engineering (AREA)
  • Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
  • Chemical Or Physical Treatment Of Fibers (AREA)
  • Coloring (AREA)
  • Polysaccharides And Polysaccharide Derivatives (AREA)
  • Yarns And Mechanical Finishing Of Yarns Or Ropes (AREA)
EP97926908A 1996-06-21 1997-06-19 Procede de traitement de fibres de cellulose et de structures constituees de ces fibres Expired - Lifetime EP0904444B1 (fr)

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
AT0110796A AT409144B (de) 1996-06-21 1996-06-21 Verfahren zur behandlung von cellulosefasern und von gebilden aus diesen fasern
AT1107/96 1996-06-21
AT110796 1996-06-21
PCT/AT1997/000132 WO1997049856A1 (fr) 1996-06-21 1997-06-19 Procede de traitement de fibres de cellulose et de structures constituees de ces fibres

Publications (2)

Publication Number Publication Date
EP0904444A1 true EP0904444A1 (fr) 1999-03-31
EP0904444B1 EP0904444B1 (fr) 1999-11-24

Family

ID=3506742

Family Applications (1)

Application Number Title Priority Date Filing Date
EP97926908A Expired - Lifetime EP0904444B1 (fr) 1996-06-21 1997-06-19 Procede de traitement de fibres de cellulose et de structures constituees de ces fibres

Country Status (15)

Country Link
US (1) US6022378A (fr)
EP (1) EP0904444B1 (fr)
JP (1) JP2000513412A (fr)
CN (1) CN1146684C (fr)
AT (2) AT409144B (fr)
AU (1) AU721876B2 (fr)
BR (1) BR9709916A (fr)
CA (1) CA2258500A1 (fr)
DE (1) DE59700768D1 (fr)
ES (1) ES2142167T3 (fr)
GR (1) GR3032485T3 (fr)
ID (1) ID17073A (fr)
NO (1) NO985955L (fr)
TW (1) TW336966B (fr)
WO (1) WO1997049856A1 (fr)

Families Citing this family (13)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0903434B1 (fr) * 1997-09-17 2002-11-27 Lenzing Aktiengesellschaft Procédé pour le traitement de fibres cellulosiques
DE59806420D1 (de) * 1997-09-17 2003-01-09 Chemiefaser Lenzing Ag Verfahren zur Behandlung von Cellulosefasern
AT2256U1 (de) 1997-10-15 1998-07-27 Chemiefaser Lenzing Ag Verfahren zur behandlung von cellulosischen formkörpern
GB2373784A (en) * 2001-03-30 2002-10-02 Tencel Ltd Lyocell fibre and treatment to reduce fibrillation
AT411863B (de) * 2002-09-16 2004-07-26 Chemiefaser Lenzing Ag Decke, vorzugsweise steppdecke
US7575599B2 (en) * 2004-07-30 2009-08-18 Spinalmotion, Inc. Intervertebral prosthetic disc with metallic core
WO2005057265A1 (fr) * 2003-12-09 2005-06-23 Matsushita Electric Industrial Co., Ltd. Pilote de l'objectif, dispositif d'imagerie, barillet de l'objectif utilise dans le dispositif d'imagerie et corps d'appareil photo
ATA1332004A (de) * 2004-01-30 2005-10-15 Chemiefaser Lenzing Ag Verfahren zur behandlung von lösungsmittelgesponnenen cellulosischen fasern
AT507051B1 (de) 2008-06-27 2015-05-15 Chemiefaser Lenzing Ag Cellulosefaser und verfahren zu ihrer herstellung
US9416494B2 (en) * 2012-12-26 2016-08-16 Kimberly-Clark Worldwide, Inc. Modified cellulosic fibers having reduced hydrogen bonding
US8980054B2 (en) * 2012-12-26 2015-03-17 Kimberly-Clark Worldwide, Inc. Soft tissue having reduced hydrogen bonding
WO2016178662A1 (fr) * 2015-05-04 2016-11-10 Carbtex Technology, Inc. Articles de fibres de coton ignifuge
EP3771755A1 (fr) 2019-08-02 2021-02-03 Lenzing Aktiengesellschaft Procédé de fabrication de fibres discontinues lyocellulaires

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Publication number Priority date Publication date Assignee Title
NL125292C (fr) * 1962-08-22
US3508858A (en) * 1966-01-11 1970-04-28 Bemberg Spa Process and product for improving the textile characteristics of natural and synthetic fibers and fibers obtained thereby
US4246221A (en) * 1979-03-02 1981-01-20 Akzona Incorporated Process for shaped cellulose article prepared from a solution containing cellulose dissolved in a tertiary amine N-oxide solvent
DE3045471A1 (de) * 1980-12-02 1982-07-08 Bayer Ag, 5090 Leverkusen Dioxazin-reaktivfarbstoffe, verfahren zu ihrer herstellung und ihre verwendung zum faerben und bedrucken von hydroxyl- oder amidgruppenhaltigen fasermaterialien
GB8303850D0 (en) * 1983-02-11 1983-03-16 Wool Dev International Textile treatment
EP0174794A3 (fr) * 1984-09-14 1987-09-16 Wool Development International Limited Traitement de textile
DE3433983A1 (de) * 1984-09-15 1986-04-10 Hoechst Ag, 6230 Frankfurt Faserreaktive triazinverbindungen, verfahren zu ihrer herstellung und ihre verwendung
DE3740650A1 (de) * 1987-12-01 1989-06-15 Bayer Ag Verfahren zur herstellung faserreaktiver nicht-chromophorer amine
US5571444A (en) * 1989-09-11 1996-11-05 Invicta Group Industries Pty Ltd. Textile treatment
GB9022175D0 (en) * 1990-10-12 1990-11-28 Courtaulds Plc Treatment of fibres
GB9122318D0 (en) * 1991-10-21 1991-12-04 Courtaulds Plc Treatment of elongate members
GB9222059D0 (en) * 1992-10-21 1992-12-02 Courtaulds Plc Fibre treatment
TR27503A (tr) * 1993-04-21 1995-06-07 Chemiefaser Lenzing Ag Azaltilmis fibrillesme egilimine sahip olan selüloz liflerini imale mahsus yöntem.
KR0135648B1 (ko) * 1995-04-08 1998-04-22 성낙관 2환성 금속착염포르마잔유도체, 그 유도체의 제조방법, 그 유도체를 함유하는 조성물 및 그 유도체를 이용한 염색방법
CN1172513A (zh) * 1995-01-12 1998-02-04 希巴特殊化学控股公司 纤维素纺织纤维材料的染色方法
JPH09324130A (ja) * 1996-06-05 1997-12-16 Sumitomo Chem Co Ltd モノアゾ化合物及びそれを用いる繊維材料の染色又は捺染方法

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Title
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Also Published As

Publication number Publication date
WO1997049856A1 (fr) 1997-12-31
AU721876B2 (en) 2000-07-13
NO985955L (no) 1999-02-03
CA2258500A1 (fr) 1997-12-31
CN1228131A (zh) 1999-09-08
GR3032485T3 (en) 2000-05-31
JP2000513412A (ja) 2000-10-10
ID17073A (id) 1997-12-04
ATE186961T1 (de) 1999-12-15
ES2142167T3 (es) 2000-04-01
AT409144B (de) 2002-05-27
AU3159497A (en) 1998-01-14
NO985955D0 (no) 1998-12-18
DE59700768D1 (de) 1999-12-30
ATA110796A (de) 2001-10-15
BR9709916A (pt) 1999-08-10
TW336966B (en) 1998-07-21
CN1146684C (zh) 2004-04-21
EP0904444B1 (fr) 1999-11-24
US6022378A (en) 2000-02-08

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