WO1999057348A1 - Fibres et filaments de polyester et procede permettant de les preparer - Google Patents

Fibres et filaments de polyester et procede permettant de les preparer Download PDF

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Publication number
WO1999057348A1
WO1999057348A1 PCT/EP1999/002888 EP9902888W WO9957348A1 WO 1999057348 A1 WO1999057348 A1 WO 1999057348A1 EP 9902888 W EP9902888 W EP 9902888W WO 9957348 A1 WO9957348 A1 WO 9957348A1
Authority
WO
WIPO (PCT)
Prior art keywords
polyamide
melt
filaments
fibers
relative viscosity
Prior art date
Application number
PCT/EP1999/002888
Other languages
German (de)
English (en)
Inventor
Raimund Schwarz
Gustav Schütze
Werner Stibal
Original Assignee
Ems-Inventa 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 Ems-Inventa Ag filed Critical Ems-Inventa Ag
Priority to KR19997012159A priority Critical patent/KR20010014109A/ko
Publication of WO1999057348A1 publication Critical patent/WO1999057348A1/fr

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/49—Phosphorus-containing compounds
    • C08K5/51—Phosphorus bound to oxygen
    • C08K5/53—Phosphorus bound to oxygen bound to oxygen and to carbon only
    • C08K5/5317—Phosphonic compounds, e.g. R—P(:O)(OR')2
    • C08K5/5333—Esters of phosphonic acids
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L67/00—Compositions of polyesters obtained by reactions forming a carboxylic ester link in the main chain; Compositions of derivatives of such polymers
    • C08L67/02—Polyesters derived from dicarboxylic acids and dihydroxy compounds
    • 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
    • D01F1/00—General methods for the manufacture of artificial filaments or the like
    • D01F1/02—Addition of substances to the spinning solution or to the melt
    • D01F1/10—Other agents for modifying properties
    • 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
    • D01F6/00—Monocomponent artificial filaments or the like of synthetic polymers; Manufacture thereof
    • D01F6/88—Monocomponent artificial filaments or the like of synthetic polymers; Manufacture thereof from mixtures of polycondensation products as major constituent with other polymers or low-molecular-weight compounds
    • D01F6/90—Monocomponent artificial filaments or the like of synthetic polymers; Manufacture thereof from mixtures of polycondensation products as major constituent with other polymers or low-molecular-weight compounds of polyamides
    • 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
    • D01F6/00—Monocomponent artificial filaments or the like of synthetic polymers; Manufacture thereof
    • D01F6/88—Monocomponent artificial filaments or the like of synthetic polymers; Manufacture thereof from mixtures of polycondensation products as major constituent with other polymers or low-molecular-weight compounds
    • D01F6/92—Monocomponent artificial filaments or the like of synthetic polymers; Manufacture thereof from mixtures of polycondensation products as major constituent with other polymers or low-molecular-weight compounds of polyesters

Definitions

  • the present invention relates to polyester fibers and filaments, which have other additives to a small extent, and a process for their production.
  • EP 0 080 274 B1 describes the addition of polyhexamethylene adipamide and polyethylene glycol to the fiber-forming polymer (polyethylene terephthalate). This brings about an increase in the elongation at break. However, spinning such mixtures is problematic. Thread breaks often occur, as can be seen from Tables 1 and 2 below (see additive types AS2503, A3 and A4).
  • polyepsiloncaproamide is in principle one of the polymers immiscible with polyethylene terephthalate.
  • polyhexamethylene adipamide is used as an additional polymer in addition to polyethylene glycol, which means for the person skilled in the art that polyamide 6 apparently performed significantly worse than polyamide 66 in the other requirements, such as spinning behavior and product properties, and was therefore not pursued as an additive.
  • the term “immiscible polymer” is understood to mean such a polymer which forms a two-phase melt with the fiber-forming thermoplastic polymer at spinning temperature. Microscopic examinations of such a melt or photographic recordings show a two-phase system in which finely divided drops of the immiscible polymer are continuously dispersed in the fiber-forming polymer matrix.
  • anisotropic melt in the temperature range at which the thermoplastic polymer can be melt-spun.
  • anisotropic conditions can be created by using liquid crystalline substances such as e.g. are described in EP 0 041 327, adding and heating polyester spinning polymers and adjusting the conditions by the action of shear forces.
  • J61266616-A (as a Derwent abstract) describes an elimination of fibrillation in polyester / polyamide mixtures at high concentration ratios
  • J56015414-A (as a Derwent abstract) admixes 10 to 30% polyester to nylon 6.
  • EP 00 47 464 B1 describes various acrylic polymers as additives, of which methyl polymethacrylic acid ester is particularly emphasized as a polymeric additive for polyethylene terephthalate (PET).
  • EP 0 631 638 B1 describes a fiber polymer which contains 0.1 to 5% by weight, based on the fiber polymer, of a 50 to 90% imidized polymethacrylic acid alkyl ester, essentially in the form of inclusions.
  • This fiber polymer shows an improved spinning behavior compared to that described in EP 0 047 464 B1, although no numerical examples are given in this regard.
  • a major disadvantage of polymethacrylic acid alkyl ester additives is the relatively high price of the additive.
  • the costs of the imidized polymethacrylic acid alkyl ester show that the economy of a process which requires the additive mentioned is not given.
  • the additive described is not available on a large scale and there is also a dependency on a few manufacturers.
  • Elongation at break values are given at spinning speeds of 3500, 6000, 7000 and 8000 m / min. However, these are not elongation values, which are advantageously required for further processing in the texturing process. For example, an elongation at break value of 65% is given at a spinning speed of 6000 m / min. However, a yarn with such an elongation cannot be used without problems in the stretch texturing process and is rather unusual. In contrast, elongation values common for the stretch texturing process are around 120%.
  • the specified elongations at spinning speeds of more than 3500 m / min refer to a highly oriented yarn for technical and textile use.
  • a special spinning device is required from a spinning speed of 6000 m / min. Accordingly, a perforated tube is used below the nozzle, which delays cooling and stabilizes the spinning process. On Such a method, which is based on passive cooling by air intake due to the filament movement, is predestined for more critical spinning processes.
  • the main disadvantage of the device described is, in particular, the associated lack of or limited flexibility in the spinning process.
  • the very important spinning speed range from 4000 to 6000 m min is not recognized in the examples of EP 0 530 652 B1.
  • this is precisely the area in which spinning crystallization clearly sets in and which would therefore be very interesting.
  • cross-flow blowing is used in this speed range.
  • a passive cooling technique is used at higher speeds, which is outstandingly suitable for rather critical speeds and / or critical melt-spinnable polymers.
  • disturbances in the spinning process may possibly occur even at spinning speeds of less than 6000 m / min.
  • cross-flow blowing can only be used to a limited extent for the polymer mixture described, and the entire process is therefore clearly limited.
  • the object of the present invention is to provide polymer mixtures for the production of polyester fibers and filaments which are readily spinnable and contain significantly less than 5% of polyamides as additives, the production process due to the small amount added, good availability of the additive and due to a strong increase in the elongation at break should be highly economical, and moreover the yellowing is reduced or eliminated, so that the products can be placed on the market.
  • polyepsiloncaprolactam (polyamide 6) from polymer mixtures of polyethylene terephthalate and small amounts. Fibers and filaments that can be produced from polyamide 12 or polyamide 6I / 6T can produce very high elongations at break, especially at high spinning speeds, and at the same time show excellent spinning behavior. Alloys of polyethylene terephthalate and polyamide 6 are known, but the tensile elongation effect in combination with an excellent spinning behavior is new. In addition, surprisingly, elongation values were achieved with relatively low additive concentrations, which are very suitable for further processing of the filaments in the stretch texturing process. Such an effect has so far been completely unknown for polyamide 12 and polyamide 6I / 6T.
  • these polymer mixtures contain an organic phosphorus stabilizer from the class of the phosphone compounds. Surprisingly, this can largely suppress yellow discoloration.
  • the polymer mixtures used according to the invention can also be spun without problems using conventional crossflow blowing, even at high spinning speeds.
  • cooling devices such as e.g. Devices for passive cooling by air intake of the high-speed threads or blowing devices, which are arranged in the center of the thread bundle.
  • polyethylene terephthalate / polyamide 6 polyethylene terephthalate / polyamide 12 and polyethylene terephthalate / polyamide 6I / 6T mixtures enormous increases in productivity are possible by increasing the elongation at break at high spinning speeds, surprisingly at the same time, despite the high Elongation, excellent spinnability of the mixture was observed.
  • polyamide 6 and polyamide 6I / 6T in particular are significantly cheaper and readily available compared to the additive component (alkyl polymethacrylate) described in EP 0 631 638 B1.
  • Polyamide 6 is not critical in large areas. A range of 2.5 to 5.2 is usually preferred in this regard. In view of the very good spinning behavior
  • Relative viscosities of 2.8 to 4.1 were found to be very suitable. Particularly suitable are relative viscosity in the range of 2.8 to 3.7.
  • polyamide 12 is additive, the commercially available Grilamid ® of type L20 of EMS-CHEMIE AG, its relative viscosity, measured at 0.5% in m-cresol at 20 ° C, in the range of 1.85 to 1.95.
  • polyamide 12 with a relative viscosity in the range from 1.6 to 2.3. The range from 1.8 to 2.0 is preferred.
  • the third type of polyamide is a partially aromatic copolyamide, which according to its nomenclature is made up of the monomers hexamethylenediamine. Isophthalic acid and terephthalic acid.
  • variable composition range ratio of the amount of isophthalic acid to the amount of terephthalic acid
  • polyamide 61 / 6T class which has an amorphous structure gives good results.
  • preference is again given to those which have a relative viscosity in the lower range, which was completely unexpected in view of the reverse statement in the prior art about nylon additives in PET (cf. EP 0 080 274 page 9).
  • Example 8th lines 30 and 31 A relative viscosity, measured at 0.5% in m-cresol at 20 ° C, is suitable. of a maximum of 1.50. The range from 1.35 to 1.45 is preferred.
  • the corresponding commercial product Grivory ® type G16 from EMS-CHEMIE AG is particularly suitable. which is amorphous with an isophthalic acid to terephthalic acid ratio of 70:30 and has a relative viscosity of approx. 1.42.
  • the concentration of the phosphonic compounds is in the range from 0.02 to 1.0% by weight.
  • the range from 0.05 to 0.6% by weight is preferably selected.
  • the admixture of the polyamide additives to the polyethylene terephthalate can be carried out, for example, by means of the so-called "melt conditioning" process for the continuous modification of polymer melts (DE 40 39 857 C2).
  • the disclosure content of DE 40 39 857 C2 is hereby also made fully part of the content of this application
  • There a part of the melt is branched off from the main melt stream. This partial stream is fed into a side-stream extruder and there the additive, which is in granular, pearl or preferably powder form, is applied and then dispersed.
  • the dispersed and mixed melt concentrate is then returned led into the main smelting line and diluted there to the final concentration.
  • melt conditioning it is also possible, for example, to produce a pure additive melt by means of a melt extruder and to inject it into the main melt stream.
  • the additive can be added both as a pure substance and in masterbatch form.
  • other additives e.g. stabilizer according to the invention
  • the polyethylene terephthalate itself can also contain the usual additives such as matting agents (titanium dioxide).
  • Stabilizers in particular the necessary according to the invention, catalysts, etc. contain.
  • PET polyethylene terephthalate
  • polyyester means the polyesters. which contain at least 80%) polyethylene terephthalate and 20%> units, derived from a diol other than ethylene glycol such as diethylene glycol. Tetramethylene glycol or an acid other than terephthalic acid, for example isophthalic acid. Hexahydroterephthalic acid. Dibenzoic acid.
  • Trimethyl propane Trimethylolethane, pentaerythritol, glycerol, trimesic acid, trimellitic acid or pyromellitic acid. modify.
  • the starting polyester can also contain known additives to modify the ability of reactive coloring, e.g. Sodium 3,5-dicarboxybenzenesulfonate.
  • dynamic and / or static mixers can also be placed directly in front of the spin pack.
  • the polyamide 6 drop sizes investigated in the examples according to the invention in the polyethylene terephthalate matrix is 250 to 400 n, i.e. less than 0.5 ⁇ m.
  • the droplet sizes (particle sizes) described in the context of the document EP 0 080 274 B1, on the other hand, are between 0.5 and 3 ⁇ m. It can therefore be assumed that in the case of very finely distributed drops in the matrix, the spinning behavior of the polymer mixture is relatively better than in the case of large deposits. which, because of their size, are at a greater relative distance from each other at the same concentration and thus have to have a less homogeneous distribution.
  • the particle size was determined on samples from the still unspun melt mixture, where the particles were still spherical. All particles were below the specified upper limit of 0.5 ⁇ m.
  • Table 1 shows results from spinning tests at a winding speed (Vwick) of 4950 m / min.
  • the spinning temperature was 292 ° C with PA6, and 295 ° C at Grilamid ® L20 and Grivory ® G16 and G21, with the range of 280 ° C to 295 ° C is preferred.
  • Conventional cross-flow blowing was used to cool the filaments. After passing through the cross-flow blower, the gam was passed over a cold godet duo and then wound up. The godet or take-off speed, ie the actual spinning speed, was 5000 m / min in all variants.
  • a normal, matted polyethylene terephthalate from EMS-CHEMIE AG with the type designation M764 was used for the production of the yarns.
  • the additives used were polyepsiloncaprolactam with the designations A23, F34. F40. F47, F50 from EMS-CHEMIE and polyhexamethylene adipamide from BASF with the type designations AS2503, A3, A4 and A5.
  • the additive was rolled up in powder form onto the polyethylene terephthalate granules.
  • the concentrations of additives PA6 and PA66 were each 1.25 percent by weight based on the polyethylene terephthalate. In the case of PA12 and PA6I / 6T, it was 3% by weight, which was added as granules (chips).
  • Table 3 shows textile data of the textile yarn.
  • the quality data achieved with the modified polyester correspond to that of good, conventionally produced texture yarn.
  • the benefit, however, is the enormous increase in productivity in the spinning mill, if you consider. that normal POY yarn is only spun at approx. 3200 m / min.
  • Viscosity (1%> - ig in H 2 S0 4 )
  • Matrix polymer unmodified PET for normal textile use (matted)

Abstract

L'invention concerne des fibres et des filaments contenant essentiellement de polyéthylèneterepthalate comme polymère fibreux, qui contient entre 0,1 à 4 % en poids, par rapport au polymère fibreux, d'un polyamide du groupe comprenant polyepsiloncaprolactame, polyamide 12 et polyamide amorphe 6I/6T, principalement sous forme d'incrustations, les polyamides ayant une viscosité relative dans des zones déterminées et le polyepsiloncaprolactme présentant une grandeur particulaire inférieure à 3 νm dans la matière en fusion. Le mélange polymère contient en outre entre 0,02 et 1,0 % en poids d'un stabilisateur de phosphore organique contre le jaunissement, sélectionné dans la catégorie des composés phosphoniques. Pour produire des fils partiellement orientés, la vitesse d'enroulement des filaments peut atteindre 8000 m/mn. L'invention concerne en outre un procédé de préparation de ce nouveau type de fibres et de filaments polyester.
PCT/EP1999/002888 1998-04-30 1999-04-28 Fibres et filaments de polyester et procede permettant de les preparer WO1999057348A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
KR19997012159A KR20010014109A (ko) 1998-04-30 1999-04-28 폴리에스터 섬유와 필라멘트 및 이들의 제조방법

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
DE19819450.1 1998-04-30
DE19819450 1998-04-30
DE19915683A DE19915683A1 (de) 1998-04-30 1999-04-07 Polyesterfasern und -filamente und Verfahren zu deren Herstellung
DE19915683.2 1999-04-07

Publications (1)

Publication Number Publication Date
WO1999057348A1 true WO1999057348A1 (fr) 1999-11-11

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KR (1) KR20010014109A (fr)
CN (1) CN1266465A (fr)
DE (1) DE19915683A1 (fr)
TW (1) TW421678B (fr)
WO (1) WO1999057348A1 (fr)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE10022889B4 (de) * 2000-05-25 2007-12-20 Lurgi Zimmer Gmbh Verfahren zum Herstellen von synthetischen Fäden aus einer Polymermischung auf Polyesterbasis
WO2010103030A3 (fr) * 2009-03-13 2010-11-25 Basf Se Mélanges stabilisés de polyester et de polyamide

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR101812237B1 (ko) * 2011-09-27 2017-12-27 코오롱인더스트리 주식회사 폴리에틸렌테레프탈레이트 연신사의 제조방법, 폴리에틸렌테레프탈레이트 연신사 및 타이어 코오드
CN102618946B (zh) * 2012-04-24 2015-10-21 可隆（南京）特种纺织品有限公司 聚对苯二甲酸乙二酯拉伸丝的制造方法、聚对苯二甲酸乙二酯拉伸丝及轮胎帘子布

Citations (9)

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Publication number Priority date Publication date Assignee Title
CH434746A (de) * 1962-12-11 1967-04-30 Geigy Ag J R Verfahren zur Herstellung von Polyestern
CH581205A5 (fr) * 1970-12-23 1976-10-29 Benecke J H Gmbh
DE2708790A1 (de) * 1977-03-01 1978-09-07 Akzo Gmbh Lineare polyester
EP0080274A2 (fr) * 1981-11-23 1983-06-01 Imperial Chemical Industries Plc Procédé pour le filage au fondu d'un mélange d'un polymère constituant la fibre et un polymère incompatible et fibres filés par ce procédé
DE4039857A1 (de) * 1990-10-19 1992-04-23 Inventa Ag Verfahren und vorrichtung zur direkten, kontinuierlichen modifizierung von polymerschmelzen
EP0501545A1 (fr) * 1991-02-28 1992-09-02 Agfa-Gevaert N.V. Méthode pour la production de polyesters à stabilité thermooxydative améliorée
JPH0617317A (ja) * 1991-12-26 1994-01-25 Toray Ind Inc ポリエステル繊維の製造方法
JPH0931739A (ja) * 1995-07-21 1997-02-04 Mitsubishi Rayon Co Ltd 多錘溶融混合紡糸方法及び多錘溶融混合紡糸装置
EP0823500A2 (fr) * 1996-08-01 1998-02-11 Zimmer Aktiengesellschaft Fibre POY en polyester pour étirage-texturation et procédé pour sa production

Patent Citations (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CH434746A (de) * 1962-12-11 1967-04-30 Geigy Ag J R Verfahren zur Herstellung von Polyestern
CH581205A5 (fr) * 1970-12-23 1976-10-29 Benecke J H Gmbh
DE2708790A1 (de) * 1977-03-01 1978-09-07 Akzo Gmbh Lineare polyester
EP0080274A2 (fr) * 1981-11-23 1983-06-01 Imperial Chemical Industries Plc Procédé pour le filage au fondu d'un mélange d'un polymère constituant la fibre et un polymère incompatible et fibres filés par ce procédé
DE4039857A1 (de) * 1990-10-19 1992-04-23 Inventa Ag Verfahren und vorrichtung zur direkten, kontinuierlichen modifizierung von polymerschmelzen
EP0501545A1 (fr) * 1991-02-28 1992-09-02 Agfa-Gevaert N.V. Méthode pour la production de polyesters à stabilité thermooxydative améliorée
JPH0617317A (ja) * 1991-12-26 1994-01-25 Toray Ind Inc ポリエステル繊維の製造方法
JPH0931739A (ja) * 1995-07-21 1997-02-04 Mitsubishi Rayon Co Ltd 多錘溶融混合紡糸方法及び多錘溶融混合紡糸装置
EP0823500A2 (fr) * 1996-08-01 1998-02-11 Zimmer Aktiengesellschaft Fibre POY en polyester pour étirage-texturation et procédé pour sa production

Non-Patent Citations (3)

* Cited by examiner, † Cited by third party
Title
DATABASE WPI Section Ch Week 9408, Derwent World Patents Index; Class A23, AN 94-062441, XP002112344 *
PATENT ABSTRACTS OF JAPAN vol. 097, no. 006 30 June 1997 (1997-06-30) *
S ASLAN ET AL: "Influence of Spinning Velocity on Mechanical and Structural Behavior of PET/Nylon 6 Fibers", JOURNAL OF APPLIED POLYMER SCIENCE, vol. 55, no. 1, 3 January 1995 (1995-01-03), pages 57 - 67, XP002112343 *

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE10022889B4 (de) * 2000-05-25 2007-12-20 Lurgi Zimmer Gmbh Verfahren zum Herstellen von synthetischen Fäden aus einer Polymermischung auf Polyesterbasis
WO2010103030A3 (fr) * 2009-03-13 2010-11-25 Basf Se Mélanges stabilisés de polyester et de polyamide

Also Published As

Publication number Publication date
DE19915683A1 (de) 1999-11-11
CN1266465A (zh) 2000-09-13
KR20010014109A (ko) 2001-02-26
TW421678B (en) 2001-02-11

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