US3576773A - Polyester based fibers comprising a non-linear branched ethylene terephthalate polymers - Google Patents

Polyester based fibers comprising a non-linear branched ethylene terephthalate polymers Download PDF

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Publication number
US3576773A
US3576773A US829954A US3576773DA US3576773A US 3576773 A US3576773 A US 3576773A US 829954 A US829954 A US 829954A US 3576773D A US3576773D A US 3576773DA US 3576773 A US3576773 A US 3576773A
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viscosity
fabric
acid
fibers
polyester
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US829954A
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Yves Vaginay
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Rhodiaceta SA
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Rhodiaceta SA
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    • 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
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
    • C08G63/02—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds
    • C08G63/12—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds derived from polycarboxylic acids and polyhydroxy compounds
    • C08G63/16—Dicarboxylic acids and dihydroxy compounds
    • C08G63/20—Polyesters having been prepared in the presence of compounds having one reactive group or more than two reactive groups
    • 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
    • D01F6/78—Monocomponent artificial filaments or the like of synthetic polymers; Manufacture thereof from copolycondensation products
    • D01F6/84—Monocomponent artificial filaments or the like of synthetic polymers; Manufacture thereof from copolycondensation products from copolyesters
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
    • C08G63/78—Preparation processes
    • C08G63/82—Preparation processes characterised by the catalyst used
    • 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
    • Y10S8/922—Polyester fiber

Definitions

  • This invention relates to polyester fibers and a process for their preparation.
  • the present invention provides oriented polyethylene terephthalate fibers which are easily accessible industrially and yarns of fibers which do not give rise to pilling. Accordingly this invention provides a polyester-based fiber having an elongation at break of greater than and a tensile strength of 18 to 36 g./tex which comprises a branched polyethylene terephthalate having a specific viscosity of 0.47 to 0.72 and a melt viscosity of 600 to 2500 poises at 285 C.
  • the fibers of this invention may be used in the manufacture of woven or knitted fabrics which substantially do not form pills.
  • the elongation of the fibers of this invention may vary within wide limits. When they are used in admixture with wool and cotton, fibers having elongations of 25 to 60% are chosen.
  • the points representing fibres of this invention are loca-ted within the area ABCD of FIG. l of the accompanying drawing.
  • the segment AB corresponds to the polymers having a viscosity 600 poises and the segment DC to the polymers having a viscosity 2,500 poises.
  • the fibers currently sold commercially correspond to points above the segment BC.
  • the fibers of this invention may be prepared by extruding, in the fused state a branched polyethylene tercphthalate containing y/ 11;-2 to z/ n-Z equivalent percent of n-valent chain units where n is 3 or 4, y is 0.2 and z is 2 having a specific viscosity of 0.47 to 0.72 and a melt viscosity of 600 to 2500 poises and orienting the yarns thus obtained by stretching.
  • the polymers used to prepare the products of this in- 'vention are branched polyethylene terephthalates and may be prepared by incorporating a branching agent, having three or four groups capable of forming stable bonds, such as ester, ether or amide bonds with the acid or alcohol groups, into the monomer mixture.
  • the preferred branching agents are polyols such as trimethylolpropane, trimethylolethane, pentaerythritol or glycerine; polyacids such as trimesic acid, trimellitic acid or anhydride or pyromellitic acid or anhydride; polyphenols such as phloroglucinol or hydroxyhydroquinone; amino acids and acid-alcohols such as hydroxyisophthalic acid or aminophthalic acid; 2,2-bis(4epoxypropoxyphenyl) -propane or diethanolamine.
  • polyols such as trimethylolpropane, trimethylolethane, pentaerythritol or glycerine
  • polyacids such as trimesic acid, trimellitic acid or anhydride or pyromellitic acid or anhydride
  • polyphenols such as phloroglucinol or hydroxyhydroquinone
  • amino acids and acid-alcohols such as
  • polyester synthesis employed 0.2 to 2 mols percent of the trifunctonal branching agent relative to the terephthalic acid, or the terephthalic acid derivative, ⁇ are used. Amounts of the order of 0.1 to 1 mol percent are preferred.
  • the polyesters which may be used in the process of this invention are essentially derived from terephthalic acid, ethylene glycol and a branching agent. They can however contain a proportion, up to 10 mol percent, of another glycol containing an aliphatic, cycloaliphatic or aromatic group or hetero-atoms such as propanediol, butanediol, hexanediol, decanediol, dimethylpropanediol, cyclohexanedimethanol, cyclobutanedimethanol, xylylene glycol, polyoxyethylene Iglycol of molecular weight less than 6,000, polytetrahydrofuran, another diacid such as adipic, sebacic, dodecanedioic, isophthalic or hexahydroor terephthalic acid, or dimeric acids derived from linoleic acid.
  • another glycol containing an aliphatic, cycloaliphatic
  • These polymers are preferaably prepared in the presence of the usual transesterification and polycondensation catalysts and may contain agents to improve their colour or heat stability such as phosphorus derivatives e.g. phosphorous acid, phosphoric acid, phenylphosphonic acid or triphenylphosphite. They can also be matted, for example by adding a suspension of titanium oxide.
  • agents to improve their colour or heat stability such as phosphorus derivatives e.g. phosphorous acid, phosphoric acid, phenylphosphonic acid or triphenylphosphite.
  • They can also be matted, for example by adding a suspension of titanium oxide.
  • Melt viscosity the viscosity in poises of the fused mass measured at 285 C.
  • Pilling the pilling observed after 30 minutes of the so-called Random Tumble Pilling Test or RTPT (Standard Specification ASTM D 1,375-64), the index l 4 so as to form a yarn of 40/1 count and with a right-hand twist of 630 (coefficient of twist 100), and this yarn is then woven into a twill fabric.
  • the woven fabric is desized, heat-set, dyed in the presence of a carrier, singed, brushed and cropped in accordance with the usual processes.
  • This Ethylene glycol 361 tendency to form pills for practical purposes can not Calcium acetate 0.805 be improved because the use of polymer or lower mo- Antimony oxide 0.110 lecular weight gives melt viscosities of less than 600 Trimethyl trimesate 1 9.5 poises, incompatible with good industrial spinning.
  • This polymer is spun at 278 C. through a spinneret on ffhe ciber hand Standard Polyester ihefs 0f SPewith 168 0.50 mm. diameter holes and the yarn is wound miic Viscosity 0-57: stretched t0 give al1 elongation at up at a speed of 900 meters per minute No adhesion be break of 22%, and converted to a fabric under the same tween the laments is Observed. conditions as above, show considerable bleaching at the After assembling several yarns, the cable is stretched at Points 0f maximum rubbing due to briilation- 100 meters per minute in a sizing bath heated to 70 C., EXAMPLE 3 EL; grrlvirr?
  • Example l using a mixture of dimethyl terephthalate, ethylene glycol, calcium acetate and phosphorous acid as in Example l, and 0.008 part of antimony oxide, it is pos- Melt viscosity Tensile Elonga- Experiment Specific (poises at Gauge strength tion at Woven Pilling Number viscosity 285 C.) (deciter) (g./tex) break fabric RTPT Fibrillation 1 0. 57 1, 200 3. 3 25 39 TWilL 5 Nil.
  • the knitted fabric When subjected to the pilling test the knitted fabric has an index of 4, which is excellent for this type of article. If the knitted fabric is subjected to brushing and cropping the index is then 5.
  • a knitted fabric obtained from a yarn of 40/1 count and coeicient of twist of 85, in a polyester/ wool mixture in the proportion of 70/ 30, is rated as 3 in the same test, and as 4-5 after cropping and brushing.
  • a knitted fabric prepared from the standard polyester described in Example 1 and treated under the same conditions is rated as follows:
  • EXAMPLE A polymer containing 1.6 equivalents of chain links derived from trimethylolpropane is prepared, spun, and knitted as above, and tested as a 70/ 30 mixture with wool.
  • EXAMPLE l 1 The polymer prepared in Example 8 is spun and stretched to give individual bers having the following properties:
  • EXAMPLE 12 The fiber of Example 11 is mixed with cotton in the proportion of 50/50 and spun into 501/ 1 (count) with a 915 right-hand twist (coefficient 130), and then knitted into gauge 20 interlock.
  • the knitted fabric After heat-setting at 210 C. and bluing in a bath, the knitted fabric is RTP'I tested and rated at 4, which is acceptable for this type of article.
  • EXAMPLE 13 A polyester which is branched with 0.8 mol percent of trimethylolpropane and which contains 6% by weight of polyoxyethylene glycol is prepared under the conditions described in Example 1 until a viscosity in the fused A11 unbranched copolyester of the same specific viscosity has the following properties under the same conditions:
  • EXAMPLE 14 This same ber :mixed with wool 70/ 30 and spun into 36/1 (count) is knitted and RTPT tested after setting and dyeing.
  • the knitted fabric is rated: 3-4 After cropping and brushing, the knited fabric is rated:
  • ethylene terephthalate polymer contains up to l0 mol percent of propanediol, butanediol, hexanediol, decanediol, dimethyl-propanediol, cyclohexane, dimethanol, cyclobutanedimethanol, xylylene glycol, polyoxyethylene glycol of molecular weight less than 6000, polytetrahydrofuran, adipic acid, sebacic acid, dodecanedioic acid, isophthalic acid, hexahydroisophthalic acid, terephthalic acid, a

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  • Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Textile Engineering (AREA)
  • Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • Artificial Filaments (AREA)
US829954A 1968-06-04 1969-06-03 Polyester based fibers comprising a non-linear branched ethylene terephthalate polymers Expired - Lifetime US3576773A (en)

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FR69050064 1968-06-04

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US (1) US3576773A (ja)
AT (1) AT303952B (ja)
BE (1) BE734017A (ja)
BR (1) BR6909153D0 (ja)
CH (1) CH518380A (ja)
DE (1) DE1928436B2 (ja)
FR (1) FR1603030A (ja)
GB (1) GB1270852A (ja)
LU (1) LU58790A1 (ja)
NL (1) NL6908117A (ja)

Cited By (30)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3960817A (en) * 1970-10-23 1976-06-01 Ciba-Geigy Ag Solid phase polyester polycondensation
US4092299A (en) * 1976-06-23 1978-05-30 Monsanto Company High draw ratio polyester feed yarn and its draw texturing
US4217440A (en) * 1979-08-20 1980-08-12 Eastman Kodak Company Method for making branched polyesters reproducibly
US4383106A (en) * 1981-09-21 1983-05-10 The Goodyear Tire & Rubber Company High melt strength elastomeric copolyesters
US4461298A (en) * 1982-07-26 1984-07-24 Ethicon, Inc. Composite sutures of silk and hydrophobic thermoplastic elastomers
US4666454A (en) * 1985-09-09 1987-05-19 Celanese Corporation Production of a fabric containing polyethylene terephthalate fibers having a reduced tendency to pill
EP0268868A2 (en) * 1986-11-07 1988-06-01 SPOFA Spojené Podniky Pro Zdravotnickou Vyrobu Pharmaceutical compositions for the treatment of gastro-intestinal diseases
US5034174A (en) * 1986-09-12 1991-07-23 E. I. Du Pont De Nemours And Company Texturing yarns
US5045260A (en) * 1985-06-21 1991-09-03 Rhone-Poulenc Viscosuisse Sa Polyester yarn and method for its manufacture
GB2245275A (en) * 1990-04-05 1992-01-02 Rhone Poulenc Fibres Process for obtaining modified polyethylene terephthalate useful for making pi lling-free fibres
EP0474418A2 (en) * 1990-08-28 1992-03-11 Hoechst Celanese Corporation Polyester copolymer fiber having enhanced strength and dyeability properties
US5180793A (en) * 1991-12-31 1993-01-19 Hoechst Celanese Corporation Flame resistant, low pilling polyester fiber
USH1275H (en) 1991-09-30 1994-01-04 E. I. Du Pont De Nemours And Company Polyester fibers
US5322921A (en) * 1985-06-21 1994-06-21 Rhone-Poulenc Viscosuisse Sa Polyester yarn
EP0604973A1 (en) * 1992-12-31 1994-07-06 Hoechst Celanese Corporation Low pilling polyester blended yarn
US5442036A (en) * 1994-09-06 1995-08-15 Eastman Chemical Company Branched copolyesters especially suitable for extrusion blow molding
US5817740A (en) * 1997-02-12 1998-10-06 E. I. Du Pont De Nemours And Company Low pill polyester
WO1999019548A1 (en) * 1997-10-14 1999-04-22 Wellman, Inc. Modified polyester with high intrinsic viscosity at moderate strength
US5968649A (en) * 1995-06-30 1999-10-19 E. I. Du Pont De Nemours And Company Drawing of polyester filaments
US6013368A (en) * 1995-06-30 2000-01-11 E. I. Du Pont De Nemours And Company Comfort by mixing deniers
WO2000012793A1 (en) * 1998-08-28 2000-03-09 Wellman, Inc. Polyester modified with polyethylene glycol and pentaerythritol
US6037055A (en) * 1997-02-12 2000-03-14 E. I. Du Pont De Nemours And Company Low pill copolyester
EP0985752A1 (de) * 1998-09-10 2000-03-15 Lurgi Zimmer Aktiengesellschaft Copolyesterfaser
WO2001036723A1 (en) * 1999-11-19 2001-05-25 Wellman, Inc. Polyethylene glycol modified polyester fibers and method for making the same
US6291066B1 (en) 1999-11-19 2001-09-18 Wellman, Inc. Polyethylene glycol modified polyester fibers and method for making the same
US20020037411A1 (en) * 2000-07-10 2002-03-28 Frankfort Hans R. Method of producing polymeric filaments
US6509091B2 (en) 1999-11-19 2003-01-21 Wellman, Inc. Polyethylene glycol modified polyester fibers
US6582817B2 (en) 1999-11-19 2003-06-24 Wellman, Inc. Nonwoven fabrics formed from polyethylene glycol modified polyester fibers and method for making the same
US6623853B2 (en) 1998-08-28 2003-09-23 Wellman, Inc. Polyethylene glycol modified polyester fibers and method for making the same
CN102974169A (zh) * 2012-12-28 2013-03-20 苏州大学 一种过滤材料及其制备方法

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4945151A (en) * 1989-03-08 1990-07-31 E. I. Du Pont De Nemours And Company Continuous production of polyester filaments
US5151494A (en) * 1991-01-04 1992-09-29 Hoechst Celanese Corporation Flame resistant, low pilling polyester fiber
DE19951067B4 (de) * 1999-10-22 2004-04-08 Inventa-Fischer Ag Polyesterfasern mit verminderter Pillingneigung sowie Verfahren zu ihrer Herstellung

Cited By (45)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3960817A (en) * 1970-10-23 1976-06-01 Ciba-Geigy Ag Solid phase polyester polycondensation
US4092299A (en) * 1976-06-23 1978-05-30 Monsanto Company High draw ratio polyester feed yarn and its draw texturing
US4217440A (en) * 1979-08-20 1980-08-12 Eastman Kodak Company Method for making branched polyesters reproducibly
US4383106A (en) * 1981-09-21 1983-05-10 The Goodyear Tire & Rubber Company High melt strength elastomeric copolyesters
US4461298A (en) * 1982-07-26 1984-07-24 Ethicon, Inc. Composite sutures of silk and hydrophobic thermoplastic elastomers
US5322921A (en) * 1985-06-21 1994-06-21 Rhone-Poulenc Viscosuisse Sa Polyester yarn
US5045260A (en) * 1985-06-21 1991-09-03 Rhone-Poulenc Viscosuisse Sa Polyester yarn and method for its manufacture
US4666454A (en) * 1985-09-09 1987-05-19 Celanese Corporation Production of a fabric containing polyethylene terephthalate fibers having a reduced tendency to pill
US5034174A (en) * 1986-09-12 1991-07-23 E. I. Du Pont De Nemours And Company Texturing yarns
EP0268868A2 (en) * 1986-11-07 1988-06-01 SPOFA Spojené Podniky Pro Zdravotnickou Vyrobu Pharmaceutical compositions for the treatment of gastro-intestinal diseases
EP0268868A3 (en) * 1986-11-07 1990-05-09 SPOFA Spojené Podniky Pro Zdravotnickou Vyrobu Pharmaceutical compositions for the treatment of gastro-intestinal diseases
GB2245275A (en) * 1990-04-05 1992-01-02 Rhone Poulenc Fibres Process for obtaining modified polyethylene terephthalate useful for making pi lling-free fibres
GB2245275B (en) * 1990-04-05 1993-09-01 Rhone Poulenc Fibres Process for obtaining modified polyethylene terephthalate useful for making pilling-free fibres
EP0474418A3 (en) * 1990-08-28 1992-07-01 Hoechst Celanese Corporation Polyester copolymer fiber having enhanced strength and dyeability properties
EP0474418A2 (en) * 1990-08-28 1992-03-11 Hoechst Celanese Corporation Polyester copolymer fiber having enhanced strength and dyeability properties
USH1275H (en) 1991-09-30 1994-01-04 E. I. Du Pont De Nemours And Company Polyester fibers
US5180793A (en) * 1991-12-31 1993-01-19 Hoechst Celanese Corporation Flame resistant, low pilling polyester fiber
EP0604973A1 (en) * 1992-12-31 1994-07-06 Hoechst Celanese Corporation Low pilling polyester blended yarn
US5442036A (en) * 1994-09-06 1995-08-15 Eastman Chemical Company Branched copolyesters especially suitable for extrusion blow molding
US5523382A (en) * 1994-09-06 1996-06-04 Eastman Chemical Company Branched copolyesters especially suitable for extrusion blow molding
US5968649A (en) * 1995-06-30 1999-10-19 E. I. Du Pont De Nemours And Company Drawing of polyester filaments
US6013368A (en) * 1995-06-30 2000-01-11 E. I. Du Pont De Nemours And Company Comfort by mixing deniers
US6214264B1 (en) * 1995-06-30 2001-04-10 E. I. Du Pont De Nemours And Company Drawing of polyester filaments
US5817740A (en) * 1997-02-12 1998-10-06 E. I. Du Pont De Nemours And Company Low pill polyester
US6037055A (en) * 1997-02-12 2000-03-14 E. I. Du Pont De Nemours And Company Low pill copolyester
WO1999019548A1 (en) * 1997-10-14 1999-04-22 Wellman, Inc. Modified polyester with high intrinsic viscosity at moderate strength
US6110587A (en) * 1997-10-14 2000-08-29 Wellman, Inc. Modified polyester with high intrinsic viscosity at moderate strength
US6221488B1 (en) 1997-10-14 2001-04-24 Wellman, Inc. Modified polyester with high intrinsic viscosity at moderate strength
WO2000012793A1 (en) * 1998-08-28 2000-03-09 Wellman, Inc. Polyester modified with polyethylene glycol and pentaerythritol
US6623853B2 (en) 1998-08-28 2003-09-23 Wellman, Inc. Polyethylene glycol modified polyester fibers and method for making the same
US6485829B2 (en) 1998-08-28 2002-11-26 Wellman, Inc. Polyester modified with polyethylene glycol and pentaerythritol
US6294254B1 (en) 1998-08-28 2001-09-25 Wellman, Inc. Polyester modified with polyethylene glycol and pentaerythritol
EP0985752A1 (de) * 1998-09-10 2000-03-15 Lurgi Zimmer Aktiengesellschaft Copolyesterfaser
US6303739B2 (en) 1999-11-19 2001-10-16 Wellman, Inc. Method of preparing polyethylene glycol modified polyester filaments
US6322886B2 (en) 1999-11-19 2001-11-27 Wellman, Inc. Polyethylene glycol modified polyester fibers, yarns, and fabrics and method for making the same
US6399705B2 (en) 1999-11-19 2002-06-04 Wellman, Inc. Method of preparing polyethylene glycol modified polyester filaments
US6454982B1 (en) 1999-11-19 2002-09-24 Wellman, Inc. Method of preparing polyethylene glycol modified polyester filaments
US6291066B1 (en) 1999-11-19 2001-09-18 Wellman, Inc. Polyethylene glycol modified polyester fibers and method for making the same
US6509091B2 (en) 1999-11-19 2003-01-21 Wellman, Inc. Polyethylene glycol modified polyester fibers
US6582817B2 (en) 1999-11-19 2003-06-24 Wellman, Inc. Nonwoven fabrics formed from polyethylene glycol modified polyester fibers and method for making the same
WO2001036723A1 (en) * 1999-11-19 2001-05-25 Wellman, Inc. Polyethylene glycol modified polyester fibers and method for making the same
US20020037411A1 (en) * 2000-07-10 2002-03-28 Frankfort Hans R. Method of producing polymeric filaments
US20040140582A1 (en) * 2000-07-10 2004-07-22 Frankfort Hans R. E. Method of producing polymeric filaments
CN102974169A (zh) * 2012-12-28 2013-03-20 苏州大学 一种过滤材料及其制备方法
CN102974169B (zh) * 2012-12-28 2014-07-02 苏州大学 一种过滤材料及其制备方法

Also Published As

Publication number Publication date
NL6908117A (ja) 1969-12-08
FR1603030A (ja) 1971-03-15
AT303952B (de) 1972-11-15
DE1928436B2 (de) 1977-08-18
CH518380A (fr) 1972-01-31
LU58790A1 (ja) 1970-01-14
GB1270852A (en) 1972-04-19
BE734017A (ja) 1969-12-03
DE1928436A1 (de) 1969-12-11
BR6909153D0 (pt) 1973-01-16

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