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EP1544331A1 - Fibres de polyester, leur procédé de fabrication et leur utilisation - Google Patents

Fibres de polyester, leur procédé de fabrication et leur utilisation Download PDF

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Publication number
EP1544331A1
EP1544331A1 EP04027655A EP04027655A EP1544331A1 EP 1544331 A1 EP1544331 A1 EP 1544331A1 EP 04027655 A EP04027655 A EP 04027655A EP 04027655 A EP04027655 A EP 04027655A EP 1544331 A1 EP1544331 A1 EP 1544331A1
Authority
EP
European Patent Office
Prior art keywords
polyester
polyester fibers
fibers according
epoxy composition
weight
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
EP04027655A
Other languages
German (de)
English (en)
Other versions
EP1544331B1 (fr
Inventor
Kurt-Günter Dr. Berndt
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.)
Teijin Monofilament Germany GmbH
Original Assignee
Teijin Monofilament Germany GmbH
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 Teijin Monofilament Germany GmbH filed Critical Teijin Monofilament Germany GmbH
Publication of EP1544331A1 publication Critical patent/EP1544331A1/fr
Application granted granted Critical
Publication of EP1544331B1 publication Critical patent/EP1544331B1/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
    • 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
    • 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
    • D01F6/58—Monocomponent artificial filaments or the like of synthetic polymers; Manufacture thereof from homopolycondensation products
    • D01F6/62—Monocomponent artificial filaments or the like of synthetic polymers; Manufacture thereof from homopolycondensation products from polyesters

Definitions

  • the present invention relates to polyester fibers having high hydrolysis resistance, in particular monofilaments, which are particularly useful in applications for Processing and / or storage of food can be used.
  • polyester fibers in particular monofilaments for technical Applications, in most cases when using high mechanical and or be subjected to thermal loads.
  • Exposure to chemical and other environmental factors affecting the material must oppose sufficient resistance. With all these burdens
  • the material needs a good dimensional stability and constancy of the force-elongation properties have as long as possible periods of use.
  • Molding compounds with high chemical and physical resistance and their Use for fiber production are known. Widely used materials for it are polyester. It is also known to use these polymers with other materials combine, for example, to set the hydrolysis resistance targeted.
  • the present invention was the The object of the invention is to provide polyester fibers which are excellent Have hydrolytic stability and are suitable for the production of Food commodities, such as conveyor belts or sieves, are suitable.
  • polyester fibers in particular Monofilaments, provided on the one hand during processing and / or storage can be used by food and the one opposite the unmodified and an equal number of carboxyl groups having polyester have improved hydrolysis resistance.
  • the invention relates to polyester fibers containing free carboxyl groups of less than 3 meq / kg, containing with an epoxy composition at least one epoxidized fatty acid ester having an epoxide content of at least 1.5% by weight, based on the composition, has been stabilized are.
  • the fiber-forming polyesters may be of any nature, as long as they are in the Melt are deformable and the fiber for the particular application lend desired properties.
  • thermoplastic polyesters and / or aromatic liquid crystalline Polyesters are known per se.
  • polyesters such as polycarbonate or aliphatic / aromatic Polyester, e.g. Polybutylene terephthalate, polycyclohexanedimethylterephthalate, Polyethylene naphthalate or in particular polyethylene terephthalate, but also completely aromatic, liquid-crystalline polyesters, such as Polyoxibenzonaphtoat.
  • Building blocks of thread-forming polyesters are preferred Diols and dicarboxylic acids, or correspondingly structured oxycarboxylic acids.
  • Main acid constituent of the polyesters is terephthalic acid or cyclohexanedicarboxylic acid, but also other aromatic and / or aliphatic or Cycloaliphatic dicarboxylic acids may be suitable, preferably para or transitive aromatic compounds, e.g. 2,6-naphthalene or 4,4'-biphenyldicarboxylic acid, but also p-hydroxybenzoic acid.
  • aliphatic Dicarboxylic acids e.g. Adipic acid or sebacic acid are preferably used in Used in combination with aromatic dicarboxylic acids.
  • Typical suitable dihydric alcohols are aliphatic and / or cycloaliphatic and / or aromatic diols, for example ethylene glycol, Propanediol, 1,4-butanediol, 1,4-cyclohexanedimethanol but also hydroquinone.
  • Preferred are aliphatic diols having from two to four carbon atoms, in particular ethylene glycol; furthermore preferred are cycloaliphatic diols, such as 1,4-cyclohexanedimethanol.
  • polyesters which contain recurring structural units which are derived from an aromatic dicarboxylic acid and a aliphatic and / or cycloaliphatic diol.
  • thermoplastic polyesters are selected in particular from the group consisting of polyethylene terephthalate, polyethylene naphthalate, Polybutylene naphthalate, polypropylene terephthalate, polybutylene terephthalate, Polycyclohexanedimethanol terephthalate, polycarbonate or a copolycondensate containing polybutylene glycol, terephthalic acid and Naphthalenedicarboxylic.
  • thermoplastic polyesters used are aromatic, liquid crystalline polyesters, in particular polyesters containing p-hydroxybenzoate units.
  • the inventively stabilized polyester moldings show a significant Reduction of the degradation tendency of the polyester, so that, for example Lifes of monofilaments can be achieved that of Monofilaments based on extremely durable fiber materials, such as Polyarylene sulfides or oxides, are equivalent.
  • the polyesters used according to the invention usually have Solution viscosities (IV values) of at least 0.60 dl / g, preferably from 0.60 to 1.05 dl / g, particularly preferably from 0.62 to 0.93 dl / g, (measured at 25 ° C in Dichloroacetic acid (DCE)).
  • IV values Solution viscosities
  • the hydrolysis protectants used according to the invention confer the Polyester fibers provide excellent protection against hydrolysis without being toxic Act.
  • the hydrolysis protective agents used according to the invention can be prepared by simple Mixing the components are made.
  • hydrolysis protection agent used according to the invention epoxidized fatty acid esters are derived from any fatty acids with any, preferably aliphatic alcohols are esterified.
  • the fatty acids have six to thirty carbon atoms, in particular ten to twenty carbon atoms.
  • the for the production of Hydrolysis protectants used according to the invention used epoxidized Fatty acid esters have at least one double bond. This can be in the Alcohol part or preferably located in the acid part. There are also fatty acid esters with several double bonds can be used as starting materials. In these Compounds are, in particular, esters of the so-called omega fatty acids, which occur for example in fish oils.
  • the alcohols can tertiary, secondary or primary aliphatic alcohols are and generally have one to ten carbon atoms.
  • Preferably used hydrolysis stabilizers comprise a) epoxidized Fatty acid alkyl esters and b) epoxidized fatty acid glycerides.
  • the epoxidized fatty acid glycerides used as component b) are derived from Any fatty acids that are esterified with glycerol or partially esterified.
  • the fatty acids Preferably, the fatty acids have six to thirty carbon atoms, in particular ten to twenty carbon atoms.
  • the fatty acids are preferred unsaturated and may have one or more double bonds.
  • epoxidized fatty acid glycerides are epoxidized soybean oil, epoxidized linseed oil, epoxidized rapeseed oil, epoxidized sunflower oil and epoxidized fish oil.
  • the epoxidized fatty acid esters used are preferably the thermally stable C 1 -C 8 -alkyl esters, in particular the 2-ethylhexyl esters, unsaturated fatty acids or fatty acid mixtures of rapeseed oil, linseed oil, soybean oil or fish oil.
  • the preparation of the epoxidized products can by known per se Epoxidation of the corresponding starting materials (esters or glycerides) with Per compounds, such as peracids or hydrogen peroxide, or with activated Oxygen, for example, with ozone, done.
  • the epoxide content of the hydrolysis stabilizer used according to the invention can also vary widely, but is at least 1.5 wt.% To Oxygen, based on the total amount of epoxidized components.
  • the epoxide content is in the range of 1.5 to 15 weight percent, in particular from 4 to 8% by weight.
  • the quantitative ratio of component a) to b) can be in a wide range vary. Typically, the amount of component a) is 90 to 10% by weight. and the amount of component b) is 10 to 90% by weight, based on the Total amount of components a) and b).
  • the nature and amount of the components a) and b) are preferably chosen so that liquid products are obtained.
  • the hydrolysis protection agent used according to the invention preferably still contains at least one carbodiimide as component c).
  • the hydrolysis-protecting agent preferably has 90 to 10 % By weight of component a), 9.9 to 60% by weight of component b) and 0.1 to 30% by weight Component c) (based on the total amount of components a) to c)).
  • the NCN content is at least 2.0 wt.%, Based on the Total amount of components a) to c).
  • hydrolysis protection agent which exclusively consists of the components a) and b).
  • polyester fibers of the invention or in the Production of the polyester added amount of epoxy composition is so too Choose the desired content of free carboxyl groups from 0 to 3 mval / kg, preferably not more than 2 meq / kg polyester.
  • the amount of epoxy composition can be chosen so that after the setting of the desired content of free carboxyl groups practically all epoxide groups are consumed.
  • the amount of epoxy composition is 0.05 to 30 wt%, based on the polyester fiber.
  • polyester fibers are any polyesters to understand containing fibers.
  • Examples include filaments or staple fibers, which consist of several individual Consist of fibers, but in particular monofilaments.
  • polyester fibers according to the invention can be prepared by processes known per se getting produced.
  • the amount of the epoxy composition should be chosen so that the content of free carboxyl groups in the polyester fiber does not exceed 3 meq / kg.
  • the amount of epoxy composition is to be chosen so the content of free carboxyl groups in the polyester fiber is not 3 meq / kg exceeds.
  • the formed polyester filament one or more times stretched.
  • polyester fibers according to the invention can be present in any desired form, for example as multifilaments, as staple fibers or in particular as Monofilaments.
  • the titer of the polyester fibers according to the invention can also be in wide Ranges vary. Examples are 100 to 45,000 dtex, especially 400 up to 7,000 dtex.
  • monofilaments whose cross-sectional shape is round, oval or n-sided, where n is greater than or equal to 3.
  • polyester fibers according to the invention may be a commercial Polyester raw material can be used. This typically has levels of free carboxyl groups of 15 to 50 meq / kg of polyester. To be favoured used by solid phase condensation polyester raw materials used; at the content of free carboxyl groups is typically 5 to 20 m / kg, preferably less than 8 meq / kg of polyester.
  • polyester raw material For the preparation of the polyester fibers according to the invention but also already hydrolysis stabilized polyester raw material can be used. In its production was the stabilizer mixture containing components a) and b) during the Polycondensation and / or added to at least one of the monomers.
  • This Polyester raw material already has a content of Carboxyl groups of less than or equal to 3 meq / kg.
  • the hot Polymer thread After pressing the polymer melt through a spinneret is the hot Polymer thread cooled, e.g. in a cooling bath, preferably in a water bath, and then wound up or peeled off.
  • the peel rate is this is greater than the injection rate of the polymer melt.
  • the polyester fiber thus produced is then preferably a Post-drawing, particularly preferably in several stages, in particular one two- or three-stage re-drawing, with a total draw ratio from 3: 1 to 8: 1, preferably 4: 1 to 6: 1.
  • polyester fibers according to the invention As particularly advantageous for the production of the polyester fibers according to the invention it has been proven, if at a melt temperature in the range of 285 to 315 ° C and a delay of 2: 1 to 6: 1 is worked.
  • the take-off speed is usually 10-100 m per minute, preferably 10 - 40 m per minute.
  • polyester fibers of the invention can be used in addition to the hydrolysis stabilizer still contain other auxiliaries.
  • auxiliaries are processing aids, Antioxidants, plasticizers, lubricants, pigments, matting agents, Viscosity modifier or crystallization accelerator.
  • processing aids are siloxanes, waxes or longer chain Carboxylic acids or their salts, aliphatic, aromatic esters or ethers.
  • antioxidants are phosphorus compounds, such as phosphoric acid esters or hindered phenols.
  • pigments or matting agents examples include organic dye pigments or titanium dioxide.
  • viscosity modifiers are polybasic carboxylic acids and their esters or polyhydric alcohols.
  • polyester fibers of the invention are used in particular for the production Objects involved in the processing and / or storage of food used.
  • polyester fibers according to the invention for the production of Fabrics, in particular of woven fabrics, used in the used in the food processing industry.
  • polyester fibers according to the invention in the form of Monofilaments relates to their use as conveyor belts or as components of Conveyor belts in the food processing industry.
  • PET polyethylene terephthalate
  • hydrolysis stabilizer hydrolysis stabilizer
  • PET a solid phase-condensed type containing free Carboxyl groups of about 7 meq / kg used.
  • Hydrolysestabilisator was a mixture of epoxidized fatty acid alkyl esters and epoxidized fatty acid glycerides used (test product Synbio Hystab the Fa. Schfer-Additivsysteme GmbH, Slevogtweg 10, 67122 Altrip).

Landscapes

  • Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Textile Engineering (AREA)
  • Artificial Filaments (AREA)
  • Polyesters Or Polycarbonates (AREA)
  • Woven Fabrics (AREA)
  • Belt Conveyors (AREA)
EP04027655A 2003-12-19 2004-11-22 Fibres de polyester, leur procédé de fabrication et leur utilisation Expired - Lifetime EP1544331B1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE10359763 2003-12-19
DE10359763A DE10359763B4 (de) 2003-12-19 2003-12-19 Polyesterfasern, Verfahren zu deren Herstellung und deren Verwendung

Publications (2)

Publication Number Publication Date
EP1544331A1 true EP1544331A1 (fr) 2005-06-22
EP1544331B1 EP1544331B1 (fr) 2009-09-09

Family

ID=34485495

Family Applications (1)

Application Number Title Priority Date Filing Date
EP04027655A Expired - Lifetime EP1544331B1 (fr) 2003-12-19 2004-11-22 Fibres de polyester, leur procédé de fabrication et leur utilisation

Country Status (7)

Country Link
US (1) US20050137299A1 (fr)
EP (1) EP1544331B1 (fr)
JP (1) JP2005179879A (fr)
AT (1) ATE442469T1 (fr)
DE (2) DE10359763B4 (fr)
ES (1) ES2332718T3 (fr)
PT (1) PT1544331E (fr)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2015047988A1 (fr) * 2013-09-30 2015-04-02 3M Innovative Properties Company Compositions, lingettes, et procédés
CN105579630A (zh) * 2013-09-30 2016-05-11 3M创新有限公司 纤维、擦拭物和方法
EP3052697A1 (fr) * 2013-09-30 2016-08-10 3M Innovative Properties Company Fibres et lingettes sur lesquelles est déposé un ester gras époxydé, et procédés

Families Citing this family (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE102004044326A1 (de) * 2004-09-10 2006-03-16 Mitsubishi Polyester Film Gmbh Hydrolysebeständige Folie aus einem Polyester mit Hydrolyseschutzmittel sowie Verfahren zu ihrer Herstellung und ihre Verwendung
GB0915687D0 (en) 2009-09-08 2009-10-07 Dupont Teijin Films Us Ltd Polyester films
GB2488787A (en) 2011-03-07 2012-09-12 Dupont Teijin Films Us Ltd Stabilised polyester films
JP5542085B2 (ja) * 2011-03-31 2014-07-09 帝人株式会社 前処理ポリエステル繊維の製造方法
JP5542084B2 (ja) * 2011-03-31 2014-07-09 帝人株式会社 ゴム補強用ポリエステル繊維
JP6151260B2 (ja) * 2011-10-14 2017-06-21 ガラタ ケミカルズ，エルエルシー 再生可能原料から誘導される可塑剤
MX357165B (es) * 2012-02-08 2018-06-28 Dow Global Technologies Llc Composiciones de plastificante y metodos para fabricar composiciones de plastificante.
GB201310837D0 (en) 2013-06-18 2013-07-31 Dupont Teijin Films Us Ltd Polyester film -IV
GB201317551D0 (en) 2013-10-03 2013-11-20 Dupont Teijin Films Us Ltd Co-extruded polyester films
JP6360693B2 (ja) * 2014-03-14 2018-07-18 株式会社クラレ 耐光性に優れた溶融異方性芳香族ポリエステル繊維
GB201707356D0 (en) 2017-05-08 2017-06-21 Dupont Teijin Films U S Ltd Partnership Hydrolysis resistant polyester film

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4016142A (en) * 1966-11-09 1977-04-05 Millhaven Fibers, Ltd. Process for the control of carboxyl end groups in fiber-forming polyesters
JPS62243825A (ja) * 1986-04-17 1987-10-24 Asahi Chem Ind Co Ltd ポリエステルフイラメントの製造方法
JPH09263688A (ja) * 1996-03-28 1997-10-07 Toray Ind Inc ポリエステル組成物、モノフィラメントおよび工業用織物
US20040214984A1 (en) * 2003-04-24 2004-10-28 Keep Gerald Timothy Stabilized polyester fibers and films

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Publication number Priority date Publication date Assignee Title
BE618033A (fr) * 1961-06-01
GB1093840A (en) * 1965-11-29 1967-12-06 Ici Ltd Modified polyesters
US3886104A (en) * 1973-01-05 1975-05-27 Gen Electric Stabilized polyester compositions
JP3001945B2 (ja) * 1990-09-20 2000-01-24 ポリプラスチックス株式会社 溶融時に異方性を示すポリエステル
JP3228977B2 (ja) * 1991-03-14 2001-11-12 ジョーンズ・マンヴィル・インターナショナル・インコーポレーテッド カルボジイミド変性ポリエステル繊維およびその製造方法
DE19540320A1 (de) * 1995-10-28 1997-04-30 Herberts & Co Gmbh Nichtionische Emulgatoren
US5753166A (en) * 1996-04-29 1998-05-19 Eastman Chemical Company Process of making a non-circular cross-sectional fiber
US6333363B1 (en) * 1997-07-18 2001-12-25 Nisshinbo Industries, Inc. Method for obtaining polyester resin products having desired strength, and mixture used in said method

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4016142A (en) * 1966-11-09 1977-04-05 Millhaven Fibers, Ltd. Process for the control of carboxyl end groups in fiber-forming polyesters
JPS62243825A (ja) * 1986-04-17 1987-10-24 Asahi Chem Ind Co Ltd ポリエステルフイラメントの製造方法
JPH09263688A (ja) * 1996-03-28 1997-10-07 Toray Ind Inc ポリエステル組成物、モノフィラメントおよび工業用織物
US20040214984A1 (en) * 2003-04-24 2004-10-28 Keep Gerald Timothy Stabilized polyester fibers and films

Non-Patent Citations (2)

* Cited by examiner, † Cited by third party
Title
PATENT ABSTRACTS OF JAPAN vol. 012, no. 122 (C - 488) 15 April 1988 (1988-04-15) *
PATENT ABSTRACTS OF JAPAN vol. 1998, no. 02 30 January 1998 (1998-01-30) *

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2015047988A1 (fr) * 2013-09-30 2015-04-02 3M Innovative Properties Company Compositions, lingettes, et procédés
CN105579630A (zh) * 2013-09-30 2016-05-11 3M创新有限公司 纤维、擦拭物和方法
EP3052697A1 (fr) * 2013-09-30 2016-08-10 3M Innovative Properties Company Fibres et lingettes sur lesquelles est déposé un ester gras époxydé, et procédés
US9982128B2 (en) 2013-09-30 2018-05-29 3M Innovative Properties Company Fibers, wipes, and methods

Also Published As

Publication number Publication date
ES2332718T3 (es) 2010-02-11
DE10359763B4 (de) 2007-11-22
US20050137299A1 (en) 2005-06-23
ATE442469T1 (de) 2009-09-15
EP1544331B1 (fr) 2009-09-09
DE502004010034D1 (de) 2009-10-22
JP2005179879A (ja) 2005-07-07
PT1544331E (pt) 2009-11-23
DE10359763A1 (de) 2005-07-28

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