US3526571A - Highly shrinkable polyamide fibres - Google Patents

Highly shrinkable polyamide fibres Download PDF

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Publication number
US3526571A
US3526571A US594496A US3526571DA US3526571A US 3526571 A US3526571 A US 3526571A US 594496 A US594496 A US 594496A US 3526571D A US3526571D A US 3526571DA US 3526571 A US3526571 A US 3526571A
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United States
Prior art keywords
fibre
component
fibres
copolyamide
nylon
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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
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US594496A
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English (en)
Inventor
Fumimaro Ogata
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Kanebo Ltd
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Kanebo Ltd
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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
    • D01F8/00—Conjugated, i.e. bi- or multicomponent, artificial filaments or the like; Manufacture thereof
    • D01F8/04—Conjugated, i.e. bi- or multicomponent, artificial filaments or the like; Manufacture thereof from synthetic polymers
    • D01F8/12—Conjugated, i.e. bi- or multicomponent, artificial filaments or the like; Manufacture thereof from synthetic polymers with at least one polyamide as constituent
    • D—TEXTILES; PAPER
    • D01—NATURAL OR MAN-MADE THREADS OR FIBRES; SPINNING
    • D01D—MECHANICAL METHODS OR APPARATUS IN THE MANUFACTURE OF ARTIFICIAL FILAMENTS, THREADS, FIBRES, BRISTLES OR RIBBONS
    • D01D5/00—Formation of filaments, threads, or the like
    • D01D5/28—Formation of filaments, threads, or the like while mixing different spinning solutions or melts during the spinning operation; Spinnerette packs therefor
    • D01D5/30—Conjugate filaments; Spinnerette packs therefor
    • D01D5/34—Core-skin structure; Spinnerette packs therefor
    • 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
    • Y10S425/00—Plastic article or earthenware shaping or treating: apparatus
    • Y10S425/217—Spinnerette forming conjugate, composite or hollow filaments
    • 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
    • Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
    • Y10T428/00—Stock material or miscellaneous articles
    • Y10T428/29—Coated or structually defined flake, particle, cell, strand, strand portion, rod, filament, macroscopic fiber or mass thereof
    • Y10T428/2913—Rod, strand, filament or fiber
    • Y10T428/2929—Bicomponent, conjugate, composite or collateral fibers or filaments [i.e., coextruded sheath-core or side-by-side type]
    • 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
    • Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
    • Y10T428/00—Stock material or miscellaneous articles
    • Y10T428/29—Coated or structually defined flake, particle, cell, strand, strand portion, rod, filament, macroscopic fiber or mass thereof
    • Y10T428/2913—Rod, strand, filament or fiber
    • Y10T428/2933—Coated or with bond, impregnation or core
    • Y10T428/2964—Artificial fiber or filament
    • Y10T428/2967—Synthetic resin or polymer
    • Y10T428/2969—Polyamide, polyimide or polyester

Definitions

  • the present invention relates to an improved highly shrinkable polyamide fibre in which a copolyamide having a high thermal shrinkability is arranged in the core portion and a homopolyamide is concentrically arranged in the surrounding portion and method of producing said fibres.
  • copolyamide contains more than about 5% by weight of copolymerizable component
  • tension irregularities occur due to the sticking and cohesion by fusion between said fibres, so that it is hardly possible to obtain homogeneous fibres free from yarn breakage and unevenness of the size of filament.
  • the electrolytic property of the copolymerizable component causes the coagulation of the titanium oxide, with the result that the copolyamide thus obtained includes unevenly distributed titanium oxide particles which will cause troubles such as yarn break- 3,526,571 Patented Sept. 1, 1970 age and unevenness of the size of filament in various processes after spinning.
  • an object of the present invention is to eliminate these drawbacks as found in such conventional fibres and provide an extremely homogeneous and highly shrinkable polyamide fibre which is free from troubles such as unevenness of the size of filament and yarn breakage due to the sticking and cohesion by fusion between fibres in various processes after spinning in spite of the fact that use is made of a copolyamide which contains a large amount of copolymerizable component.
  • Another object of the invention is to provide a highly shrinkable fibre which is excellent in heat resistance and light resistance as compared with the conventional highly shrinkable polyamide fibres.
  • the method according to the invention is characterized by the simultaneous melt spinning of copolyamide and homopolyamide through the same orifice in such a manner that the copolyamide component forms a core portion throughout the entire length of the unitary fibre and the homopolyamide having a substantially uniform thickness forms a sheath completely surrounding said copolyamide component, the thickness of the homopolyamide component being controlled so as to be 1-15% of the diameter of the unitary fibre.
  • FIG. 1 shows a vertical sectional View of a spinneret apparatus used in the production of fibres according to the invention
  • FIG. 2 shows an enlarged cross-sectional view of fibres obtained according to the invention.
  • a spinneret 9 has an annular supply chamber 1 completely separated by an annular partition wall 13, and a cylindrical central supply chamber 2, these supply chambers 1 and 2 being provided at their bottoms with communication holes 3 and 6, respectively, leading to the lower part.
  • a nozzle plate 10 has a raised annular edge 12 and an annular groove 5 provided with orifices 8 at its bottom.
  • the nozzle plate 10 is firmly pressed and fixed to the lower surface of the spinneret 9 at the surface of the raised edge 12 by a retainer ring 11.
  • the axis of introduction holes 4 projecting downwardly from the communication holes 3 are arranged so as to be perfectly aligned with the axis of the orifices 8.
  • a space chamber 7 is defined between the lower surface of the spinneret 9 and the nozzle plate 10.
  • a molten copolyamide component A is supplied to the annular supply chamber 1 and a homopolyamide component B is supplied to the central supply chamber 2.
  • the component A is extruded through the communication hole 3 into the annular groove 5.
  • the component B flows through the communication hole 6 and the space chamber 7 into the annular groove 5 and surrounds the component A, and the component A surrounded by the component B is extruded through the associated spinning hole 8 to form such a fibre that the component A is surrounded concentrically by the component B.
  • a typical example of the fibre thus obtained is shown in enlarged cross-sectional view in FIG. 2.
  • the component A is completely surrounded by the component B. If the component A should be exposed to the outside even though slightly, in such exposed areas not only objectionable phenomena such as sticking and cohesion by fusion but also irregularities in strength, elongation, light resistance, heat resistance and other properties would occur, thereby the quality of yarn is considerably decreased. Moreover, the thickness of the sheath, that is, component B should be substantially uniform over the total periphery portion and the total length of the fibre.
  • the method of the present invention does not aim crimpability as seen from the object, but aims production of a highly shrinkable fibre having no loops and crimps for particular applications, so that both of the components A and B should be concentrically arranged. If the component B should happen to have irregularities in thickness, this would give the possibility of developing loops and crimps during heat treatment or cause irregularities in the quantity of yarn, so it is not preferable.
  • the apparatus of the type shown in FIG. 1 not only the apparatus of the type shown in FIG. 1 but also other types of spinning apparatuses can be used. It is, however, essential in every case to spin such a manner that the copolyamide component may be arranged in the core portion and the homopolyamide component may surround said copolyamide.
  • the thickness of the homopolyamide component which surrounds said copolyamide is preferably 1-15% of the diameter of the fibre. If the thickness of the homopolyamide component is less than 1% of the diameter of the fibre, such thickness is insufiicient for preventing various drawbacks of copolyamide component, so that there will be troubles such as sticking, unevenness of the size of filament, and yarn breakage as has been in the case of the conventional fibres, and, moreover, the resulting fibre will be extremely poor in heat resistance and light resistance.
  • the thickness of the homopolyamide falls within the above mentioned range, a fibre is more excellent in shrinkability, heat resistance and light resistance as compared with the conventional shrinkable fibre can easily be obtained.
  • the thickness of the homopolyamide component may be suitably selected depending upon the kind of the copolyamide employed and the uses of the fibres.
  • the amounts of the components A and B supplied to the supply chambers 1 and 2 are controlled by a gear pump or the like so that the bonding ratio may be 24:1 to 49:51 when both of the components are conjugate spun.
  • the homopolyamides and copolyamides used in the present invention include various polyamide groups.
  • the homopolyamides mention may be made of nylon-6, nylon-66, nylon-610, nylon-7, nylon-11, nylon-12, polymetaxylene diammonium adiapte, polyparaxylene diammonium adipate and etc.
  • copolyamides mentioned may be made of copolymer nylons obtained by the optional combination of two or more of such polyamide-forming substances as e-caprolactam, nylon-66 salt, nylon-610 salt, nylon-l2 salt, metaxylylene diammonium adipate, paraxylylene diammonium adipate, hexamethylene diammonium terephthalate, hexamethylene diammonium isophthalate and etc.
  • a copolyamide which is a highly shrinkagle component is arranged in the core portion and a homopolyamide is arranged so as to surround said copolyamide component, whereby drawbacks such as sticking and cohession by fusion between fibres in various processes after spinning can be eliminated and moveover a highly shrinkable polyamide fibre which is excellent in light resistance and heat resistance can be obtained, so that the obtained fibre can be utilized in a very large field compared with the conventional fibres.
  • EXAMPLE 1 A copolymer nylon (component A) having a relative viscosity of 2.6 measured in 98% sulphuric acid which was obtained by the copolymerization of parts of e-caprolactam and 25 parts of hexamethylene diammonium isophthalate (said copolymer nylon being hereinafter abbreviated to 6/6I), and nylon-6 (component B) having a relative viscosity of 2.7 were simultaneously spun through the same orifice at a conjugate ratio of 20:1 by using the apparatus shown in FIG. 1, and then the resulting 70 denier non-stretched fibre was Wound on a bobbin.
  • component A having a relative viscosity of 2.6 measured in 98% sulphuric acid which was obtained by the copolymerization of parts of e-caprolactam and 25 parts of hexamethylene diammonium isophthalate
  • nylon-6 component B having a relative viscosity of 2.7 were simultaneously spun through the same orific
  • the shrinking percentage in hot water of the stretched fibre was excellent such as 41%.
  • shrinking percentage in hot water here refers to a shrinking percentage measured after the material is immersed in boiling water for 10 minutes under a load of 0.5 g./d.).
  • 6/61 (whose ratio by weight is /15) having a relative viscosity of 2.6 was spun solely, and the resulting fibre was stretched to 4.2 times into original length.
  • the stretched fibre was partially stuck between the filaments, so that the filaments cannot easily be unwound from the bobbin and yarn breakage occurred between stretching rollers. Thus, a satisfactory stretched yarn could not be obtained.
  • EXAMPLE 2 To a molten mixture consisting of parts of caprolactam and 10 parts of a salt of m-xylylene diamine and adipic acid was added 0.4 part of adipic acid while stirring, and then the resulting mixture was copolymerized at a temperature of 80 C. for 8 hours to obtain a copolymer nylon having a relative viscosity of 2.4 (hereinafter abbreviated to 6/MXD-6).
  • the copolymer nylon (component A) and the nylon-6 (component B) used in Example 1 were melt-spun at the conjugate ratio of 5:1 by using the apparatus shown in FIG. 1 and then the resulting fibre was stretched to 4.2 times its original length to obtain a 15 denier unitary fibre (the fibre being referred to as Fibre 1).
  • the 6/MXD-6 as obtained by the copolymerizing operation mentioned above and the nylon-6 were separately melt-spun and stretched to 4.2 times its original length to obtain 15 denier unitary fibres.
  • the unitary fibre obtained from the 6/MXD6 is referred to as Fibre 2 and the other obtained from the nylon-6 is referred to as Fibre 3.
  • Fibre 1 Fibre 2 Fibre 3 Number of yarn breakage 2 11 0shrinking percentage in hot water, percent 28 32 12 Strength-preserving percentage, when not subjected to radiation, percent 100 100 100 Strength-preserving percentage, when subjected to radiation, percent 71 40 90 EXAMPLE 3
  • a copolymer nylon having a relative velocity of 2.4 (component A) obtained by the copolymerization of 70 parts of e-caprolactam and 30 parts of nylon-66 salt, and nylon-6 (component B) as used in Example 1 were meltspun in a conjugate ratio of 1:1 by using the apparatus shown in FIG. 1, and the resulting fibre was stretched to 4.2 times its original length at room temperature to obtain a 15 denier unitary fibre.
  • the thickness of the component B of this fibre was about 14.6% of the diameter of fibre, shrinking percentage in hot water being 23%.
  • a highly shrinkable polyamide filament having no stickiness between filaments which does not form loop and crimp by heating which comprises a copolyamide core component extending the total length of the filament and a homopolyamide component having a substantially uniform thickness which forms a sheath completely surrounding the copolyamide component, the thickness of the sheath being 1 to 15% of the filament diameter, said homopolyamide being selected from the group consisting of polycapramide, polyhexamethylene adipamide, polyhexamethylene sebacamide, polyheptamide, polyundecamide, polydodecamide, polymetaxylylene adipamide and polyparaxylylene adipamide, and said copolyamide being a copolymer of two or more polyamide forming materials selected from the group consisting of e-caprolactam, hexamethylene diammonium adipate, hexamethylene diammonium sebacate, w-aminododecanoic acid, metaxylylene diammonium

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  • Engineering & Computer Science (AREA)
  • Textile Engineering (AREA)
  • Mechanical Engineering (AREA)
  • Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Multicomponent Fibers (AREA)
  • Artificial Filaments (AREA)
US594496A 1965-12-01 1966-11-15 Highly shrinkable polyamide fibres Expired - Lifetime US3526571A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
JP7416665 1965-12-01

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US (1) US3526571A (instruction)
BE (1) BE690317A (instruction)
DE (1) DE1660428A1 (instruction)
FR (1) FR1502552A (instruction)
GB (1) GB1145527A (instruction)

Cited By (19)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3607610A (en) * 1967-01-31 1971-09-21 Asahi Chemical Ind Crimped composite filaments of polycaprolactam or polyhexamethylene adipamide, and a terpolyamide of e-caprolactam, hexamethylenediammonium adipate, hexamethylene diammonium sebacate
US3664917A (en) * 1968-11-25 1972-05-23 Rhodiaceda Soc Two-component polyamide yarns
US3664914A (en) * 1966-01-28 1972-05-23 Bayer Ag Bifilar compound filaments of polyamides
US3664916A (en) * 1969-09-25 1972-05-23 Rhodiaceta Polyamide-based composite filaments
US3667207A (en) * 1970-05-01 1972-06-06 Du Pont Crimpable composite polyamide yarn
US3675408A (en) * 1969-12-31 1972-07-11 Ici Ltd Polyamide filaments
US4069363A (en) * 1975-05-27 1978-01-17 E. I. Du Pont De Nemours And Company Crimpable nylon bicomponent filament and fabrics made therefrom
US4293516A (en) * 1978-11-30 1981-10-06 Imperial Chemical Industries, Limited Process for spinning bicomponent filaments
US4521484A (en) * 1984-06-07 1985-06-04 E. I. Du Pont De Nemours And Company Self-crimping polyamide filaments
US4698082A (en) * 1985-12-23 1987-10-06 Ppg Industries, Inc. Hollow fiber bushing and hollow fiber tip construction
US4717325A (en) * 1983-06-01 1988-01-05 Chisso Corporation Spinneret assembly
US4735642A (en) * 1985-10-20 1988-04-05 Ppg Industries, Inc. Hollow glass fiber bushing assembly
US4758259A (en) * 1986-10-02 1988-07-19 Ppg Industries, Inc. Hollow glass fiber bushing, method of making hollow fibers and the hollow glass fibers made by that method
EP0328969A3 (en) * 1988-02-17 1989-10-18 Chisso Corporation Spinneret assembly for sheath-core type composite fibers
EP0284784A3 (en) * 1987-04-01 1989-11-29 Neumunstersche Maschinen- und Apparatebau Gesellschaft mbH (Neumag) Spinnerette packet for bicomponent fibres having a skin-core structure
US5320512A (en) * 1992-09-24 1994-06-14 E. I. Du Pont De Nemours And Company Apparatus for spinning multicomponent hollow fibers
US6746226B2 (en) * 2000-12-08 2004-06-08 L'Air Liquide - Societe Anonyme à Directoire et Conseil de Surveillance pour l'Etude et l'Exploitation des Procedes Georges Claude Spinnerette assembly for forming multicomponent hollow fibers
US6799960B2 (en) * 2000-12-08 2004-10-05 L'air Liquide - Societe Anonyme A Directoire Et Consiel De Surveillance Pour L'etude Et L'exploitation Des Procedes Georges Claude Spinnerette assembly for forming hollow fibers
US20060008549A1 (en) * 2000-12-04 2006-01-12 Advanced Ceramics Research, Inc. Compositions and methods for preparing multiple-component composite materials

Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB830441A (en) * 1955-06-30 1960-03-16 Du Pont Process for extruding a synthetic fibre-forming liquid and a spinneret assembly for use in the process
US3118011A (en) * 1962-07-03 1964-01-14 Du Pont Process for preparing helically crimped composite filaments
GB972932A (en) * 1962-02-10 1964-10-21 British Nylon Spinners Ltd Improvements in or relating to spinnerets for the production of sheath and core heterofilaments
GB981003A (en) * 1962-08-24 1965-01-20 Onderzoekings Inst Res A process for the manufacture of synthetic multifilament threads
FR1422393A (fr) * 1963-12-07 1965-12-24 Kanegafuchi Spinning Co Ltd Procédé de fabrication de filaments composés
US3271837A (en) * 1964-09-25 1966-09-13 Du Pont Method of manufacturing stockings from two-component filaments
US3315021A (en) * 1964-06-19 1967-04-18 Snia Viscosa Process for the production of crimpable composite synthetic yarns

Patent Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB830441A (en) * 1955-06-30 1960-03-16 Du Pont Process for extruding a synthetic fibre-forming liquid and a spinneret assembly for use in the process
GB972932A (en) * 1962-02-10 1964-10-21 British Nylon Spinners Ltd Improvements in or relating to spinnerets for the production of sheath and core heterofilaments
US3118011A (en) * 1962-07-03 1964-01-14 Du Pont Process for preparing helically crimped composite filaments
GB981003A (en) * 1962-08-24 1965-01-20 Onderzoekings Inst Res A process for the manufacture of synthetic multifilament threads
FR1422393A (fr) * 1963-12-07 1965-12-24 Kanegafuchi Spinning Co Ltd Procédé de fabrication de filaments composés
US3315021A (en) * 1964-06-19 1967-04-18 Snia Viscosa Process for the production of crimpable composite synthetic yarns
US3271837A (en) * 1964-09-25 1966-09-13 Du Pont Method of manufacturing stockings from two-component filaments

Cited By (21)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3664914A (en) * 1966-01-28 1972-05-23 Bayer Ag Bifilar compound filaments of polyamides
US3607610A (en) * 1967-01-31 1971-09-21 Asahi Chemical Ind Crimped composite filaments of polycaprolactam or polyhexamethylene adipamide, and a terpolyamide of e-caprolactam, hexamethylenediammonium adipate, hexamethylene diammonium sebacate
US3664917A (en) * 1968-11-25 1972-05-23 Rhodiaceda Soc Two-component polyamide yarns
US3664916A (en) * 1969-09-25 1972-05-23 Rhodiaceta Polyamide-based composite filaments
US3675408A (en) * 1969-12-31 1972-07-11 Ici Ltd Polyamide filaments
US3667207A (en) * 1970-05-01 1972-06-06 Du Pont Crimpable composite polyamide yarn
US4069363A (en) * 1975-05-27 1978-01-17 E. I. Du Pont De Nemours And Company Crimpable nylon bicomponent filament and fabrics made therefrom
US4293516A (en) * 1978-11-30 1981-10-06 Imperial Chemical Industries, Limited Process for spinning bicomponent filaments
US4717325A (en) * 1983-06-01 1988-01-05 Chisso Corporation Spinneret assembly
US4521484A (en) * 1984-06-07 1985-06-04 E. I. Du Pont De Nemours And Company Self-crimping polyamide filaments
US4735642A (en) * 1985-10-20 1988-04-05 Ppg Industries, Inc. Hollow glass fiber bushing assembly
US4698082A (en) * 1985-12-23 1987-10-06 Ppg Industries, Inc. Hollow fiber bushing and hollow fiber tip construction
US4758259A (en) * 1986-10-02 1988-07-19 Ppg Industries, Inc. Hollow glass fiber bushing, method of making hollow fibers and the hollow glass fibers made by that method
EP0284784A3 (en) * 1987-04-01 1989-11-29 Neumunstersche Maschinen- und Apparatebau Gesellschaft mbH (Neumag) Spinnerette packet for bicomponent fibres having a skin-core structure
EP0328969A3 (en) * 1988-02-17 1989-10-18 Chisso Corporation Spinneret assembly for sheath-core type composite fibers
US5320512A (en) * 1992-09-24 1994-06-14 E. I. Du Pont De Nemours And Company Apparatus for spinning multicomponent hollow fibers
US20060008549A1 (en) * 2000-12-04 2006-01-12 Advanced Ceramics Research, Inc. Compositions and methods for preparing multiple-component composite materials
US6746226B2 (en) * 2000-12-08 2004-06-08 L'Air Liquide - Societe Anonyme à Directoire et Conseil de Surveillance pour l'Etude et l'Exploitation des Procedes Georges Claude Spinnerette assembly for forming multicomponent hollow fibers
US6799960B2 (en) * 2000-12-08 2004-10-05 L'air Liquide - Societe Anonyme A Directoire Et Consiel De Surveillance Pour L'etude Et L'exploitation Des Procedes Georges Claude Spinnerette assembly for forming hollow fibers
US20050031721A1 (en) * 2000-12-08 2005-02-10 Moore Samuel Earl Spinnerette assembly for forming hollow fibers
US7691318B2 (en) 2000-12-08 2010-04-06 L'air Liquide - Societe Anonyme A Directoire Et Conseil De Surveillance Pour L'etude Et L'exploitation Des Procedes Georges Claude Process of making hollow fibers

Also Published As

Publication number Publication date
FR1502552A (fr) 1967-11-18
BE690317A (instruction) 1967-05-02
GB1145527A (en) 1969-03-19
DE1660428A1 (de) 1972-04-20

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