US3673053A - Acrylic fibers with improved brightness and process for producing the same - Google Patents

Acrylic fibers with improved brightness and process for producing the same Download PDF

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Publication number
US3673053A
US3673053A US7858A US3673053DA US3673053A US 3673053 A US3673053 A US 3673053A US 7858 A US7858 A US 7858A US 3673053D A US3673053D A US 3673053DA US 3673053 A US3673053 A US 3673053A
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Prior art keywords
fiber
brightness
stretching
spinning
degree
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US7858A
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Inventor
Keitaro Shimoda
Nobuhiro Tsutsui
Hideto Sekiguchi
Masao Sone
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Japan Exlan Co Ltd
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Japan Exlan Co Ltd
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    • 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
    • D01D5/253—Formation of filaments, threads, or the like with a non-circular cross section; Spinnerette packs therefor
    • 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
    • D01F6/02—Monocomponent artificial filaments or the like of synthetic polymers; Manufacture thereof from homopolymers obtained by reactions only involving carbon-to-carbon unsaturated bonds
    • D01F6/18—Monocomponent artificial filaments or the like of synthetic polymers; Manufacture thereof from homopolymers obtained by reactions only involving carbon-to-carbon unsaturated bonds from polymers of unsaturated nitriles, e.g. polyacrylonitrile, polyvinylidene cyanide
    • 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
    • Y10T428/2973—Particular cross section

Definitions

  • the technique disclosed therein is directed solely to a melt-spinning system which can maintain a comparatively high degree of correlativity between the cross-sectional shape of the spinning orifice and that of the spun fiber, but has not been applicable in fact to a wet-spinning system wherein the cross-sectional shape of the fiberis determined by the correlation between the desolvating velocity when the spinning solution is extruded into the coagulating bath and the diluting velocity of the solvent and by the mechanism of the formation of a skin-core structure.
  • a principal object of the present invention is to provide a special form peculiarity of acrylic fibers remarkably improved in the brightness.
  • a second object of the present invention is to provide a new process to obtain acrylic fibers having a remarkably improved brightness represented quantitatively as a correlation with the 60-degree mirror-surface luster degree and contrast index.
  • the present invention includes two subject matters as evident from the following detailed explanation.
  • One of them is a form peculiarity defining the cross-sectional shape of acrylic fibers made by a wet-spinning method and the other is a new fiber producing process for imparting such form peculiarity to acrylic fibers by a wet-spinning method.
  • the first object of the present invention can be attained by forming a predetermined curved peripheral edge defined by the following relative formulas in a triangular cross-section of an acrylic fiber produced by a wet-spinning method as exemplified in FIG. 4.
  • an acrylic synthetic fiber having a predetermined curved peripheral edge shape defined by the relative formula wherein I is a length (in microns) of one side represented a; a straight line connecting two apexes of a triangular cross-section of an acrylic fiber, a is a minimum curve height (in microns) of the peripheral edge measured in the direction vertical to the straight line connecting the two apexes of the above mentioned triangle, p is a minimum curve pitch length (in microns) of the peripheral edge measured in the direction along the straight line connecting the two apexes of the above mentioned triangle and d is a monofilament fineness (in deniers) of the acrylic fiber having the triangular cross-section.
  • the second object of the present invention is attained by adopting the later described particular fiber producing conditions in the wet-spinning of acrylic fibers by using a spinnerette having Y-shaped or approximately Y-shaped spinning orifices.
  • the acrylic fibers referred to in the present invention mean single-component fibers consisting of an acrylonitrile homopolymer or of a copolymer of at least percent by weight acrylonitrile and one or more monomer compounds copolymerizable with acrylonitrile or composite fibers made by bonding two components (polymers or copolymers) different in the thermoshrinking behavior in a core-sheath form or side-by-side form.
  • the fibers may be in the form of staples or monofilaments or multifilarnents spun in the form of continuous filaments.
  • the means of imparting a brightness to fibers to be made by a wet-spinning system wherein the cross-sectional shape in which the peripheral edge of the fiber is curved is determined by the correlation between the desolvating velocity after the spinning solution is extruded into the coagulating bath and the diluting velocity of the solvent and the formation of a skin-core structure can not be considered to be equivalent with the technique of imparting a brightness to fibers to be made by a melt-spinning system or dry-spinning system wherein a smooth peripheral shape is made and a considerable continuity is recognized between the cross-sectional shape of the spinning orifice and that of the fiber.
  • FIG. 1 is a system view of a contrast index measuring apparatus
  • FIG. 2 is a plan view of the apparatus showing the formation of the essential part in FIG. 1
  • FIG. 3 is a graph for explaining the shapes of peaks on a recording paper representing ahigh-lightness of a standard knitted texture
  • FIG. 4 is a magnified cross-sectional view of an acrylic synthetic fiber of the present invention.
  • the 60-degree mirror-surface luster degree in the present invention was measured according to the method defined in JIS Z-874l by using a GM-5 luster meter (manufactured by Murakami Color Technical Laboratory).
  • a rectangular test piece of 6 cm X 4.5 cm of a cardboard on which fiber bundles having had the crimps tensioned and stretched under heating were parallelly arranged andpasted was prepared and was measured in a position where the angle of incidence was parallel with the axial direction of the fiber.
  • the contrast index meaning the brightness based on the macroscopic form peculiarity of a fiber in the present invention will be explained.
  • the contrast index is determined by measuring a zarnple S with a scanning type microscopic luster meter consisting of an electric source stabilizer ST, voltage stabilizer EST, light source L, magnifying lens optical system EL, movable photoelectric multiplying tube R, amplifier A and recorder system REC shown in FIG. 1.
  • the light source is formed of an incadescent bulb of 12-V 30W positioned so that the angle of light incidence to the warp of the knitted texture angle of light incidence to the warp of the knitted texture sample 10 may be 45 degrees and a slide projector 11 having a lens of a focal distance of 54 mm.
  • the light source is operated with a constant voltage controlled by the electric source stabilizer ST and voltage stabilizer EST and is positioned so that, when light is focused on the sample, the distance between the lens center of the slide projector l I and the reflecting point of the light on the surface of the sample S to be measured will be 54 mm.
  • the voltage is made constantby the electric source stabilizer ST and voltage stabilizer EST, the photoelectric multiplying the tube 3 moving in a direction intersecting at right angles with the paper surface in FIG. 2 is positioned in the same plane as of the light source and the sample knitted texture 10 is positioned so that its warp direction is parallel with said horisontal surface.
  • the angle of reflection to the yarns forming the sample knitted texture 10 will be able to be defined as 0 degree.
  • the sample knitted texture 10 On a disc-shaped sample stand 9 provided rotatably in a plane parallel with the above mentioned horizontal plane, the sample knitted texture 10 is so positioned that its surface intersects at right angles with the above mentioned horizontal plane and coincides with the intersection of the respective extensions of the center lines of the light source and photoelectric multiplying tube 3.
  • the size of the knitted texture sample 10 is 450 mm.
  • a magnifying lens opticalsystem EL comprising an objective 8 of a focal distance of 10 mm. and magnification of 11.1 times, lens barrel 7 and camera obscura 6 is provided between the photoelectric multiplying tube 3 and the knitted texture sample 10.
  • the photoelectric multiplying tube 3 having a slit 4 which is 0.2 mm. long along the weft direction and 1.0 mm.
  • a stage 13 having a variable speed gear box 2 fed with a power from a variable speed motor 1 for reciprocating scanning at a fixed velocity.
  • the weft direction of the knitted texture sample 10 and the moving direction of the stage 13 are made to intersect at right angles with each other and the photoelectric multiplying tube 3 is moved by 40 mm. while maintaining a constant velocity of 8 mm. per minute along the yarn image on a frosted glass fixed to the camera obscura 6.
  • the electric output of the photoelectric multiplying tube 3 is fed through an amplifier A whose voltage is made constant in advance by the high voltage controlling device EST and low voltage controlling device ST in the same manner as in the photoelectric multiplying tube 3 or light source L to such recorder having a reverse electromotive force voltage and a full scale width of 0 to 2 mV. by the voltage divider in the recorder system REC as, for example, an LER-l2A recorder of Yokokawa Electric Machinery Manufacturing Company and is recorded on a recording paper moving while maintaining a constant velocity of 60 mm. per
  • the fine high lights reflected from the yarn surface of the knitted texture sample will be recorded as peaks H H H H and the dark parts between the high lights will be recorded as valleys L L L L,, between the peaks respectively on the recording paper.
  • the contrast index of the knitted texture sample is directly determined by the cross-sectional area and surface shape of the monofilament forming the knitted texture but is also influenced by such secondary factors as the fineness, crimped degree, yarn fineness and number of twists.
  • a structure knitted texture made by forming filaments or staples of 3 deniers into 52-denier variously twisted twin yarns of upper twists of 410 T/m and lower twists of 610 T/m and making the warp and weft densities respectively 17 yarns/25 mm. with a knitting machine of 12 gauges is used as a standard knitted texture sample.
  • filaments a plain structured texture with 30 yams/25 mm. of warp density and 200 yarns/25 mm.
  • weft density made of 400 deniers of non-texturized filaments with 2.5 or 3.0 single filament deniers knitted by a knitted machine with 12 gauges is used.
  • the larger this contrast index the clearer and stronger the microscopic spot light pencil reflected from the surface of the knitted texture sample and the more remarkable the visional brightness.
  • the brightness shown by the final product made of the obtained fibers made the contrast index 15 to 50 or more preferably 20 to 40 and the fact that a very optically excellent silky brightness was shown was also made clear.
  • the contrast property is the 60-degree mirror-surface luster degree defined by JIS Z-8741 and representing the brightness based on the peculiarity of the microscopic form of the fiber. Only by adopting the specific spinning conditions clarified to attain the later described second object of the present invention, it is possible to make the 60-degree mirror-surface reflection degree defining the quantitative level of the brightness correspond to the qualitative level of the brightness defined as the above mentioned contrast index.
  • the value of the 60-degree mirrorsurface luster degree in the present invention is at least 35. It is recognized that, in this case,.the contrast index takes a value of 15 to 50 or more preferably 20 to 40. Only when these two conditions are satisfied simultaneously, it will be possible to impart a silky calm brightness to the acrylic fiber having a triangular cross-section.
  • the acrylic fiber by a wet-spinning system having such characteristics can be attained by imparting a specific crosssectional shape represented by the following relative formulas to an acrylic synthetic fiber by adopting a series of limited spinning conditions clarified as a means of attaining the second object of the present invention.
  • the microscopic form peculiarity represented by the relative formulas 2) 8- and IH d S t a vs L and (Ix 3 16 is imparted to an acrylic fiber made by a wet-spinning method and having a triangular cross-section as a whole, the brightness of the fiber will be remarkably improved and the 60-degree mirror-surface luster degree showing the optical reflecting activity of the monofilament and the contrast index showing the brightness sensibly understood in the form of the final product will be both kept in a desirable numerical value range.
  • the second object of the present invention is attained by spinning a spinning solution into a coagulating bath at a temperature of to C. byadjusting the inorganic salt concentrations in the spinning solution and coagulating solution to be in a range of the relative formulas (wherein y is an inorganic salt concentration (in percent) in the spinning solution and x is an inorganic salt concentration (in percent) in the coagulating bath) and maintaining the delivery ratio defined as the average flow velocity of the spinning solution through the spinning orifice/the pull-out velocity of the coagulated fiber filament in a range of 0.5 to 3.0 in wet-spinning an acrylic fiber by using a spinnerette having Y-shaped or approximately Y-shaped spinning orifices and then imparting to the fiber filament a stretching represente by the following relative formula l6X,+2.5X -3X 31 (7) (wherein X 1 is a cold-stretching ratio at the room temperature, X is a primary hot-stretching ratio in hot water and X isa secondary stretching
  • the contrast index defined by 100 log(h,,/I,,) based on the macroscopic form peculiarity of the cross-section of a fiber is taken in a range of 15 to 50 or more preferably to 40 and the value of the 60-degree mirror-surface luster degree based on the microscopic form peculiarity is made at least 35, a silky calm brightness will be imparted to the acrylic fiber.
  • the value of the 60-degree mirror-surface can be represented quantitatively as a function of the stretching multiplication in a series of stretching steps from the cold-stretching to the secondary stretching by steam heat.
  • the temperature of the spinning solution is in a range of 40 to C, If the spinning solution temperature is lower than 40 C., the back pressure on the spinnerette will rise and the continuation of smooth spinning will be obstructed. In case the spinning solution temperature is higher than 80 C., the fiber forming composition will be colored and the commodity value of the obtained fiber will be remarkably reduced.
  • the coagulating velocity of the spinning solution will be accelerated in excess, a skin-core structure will be formed and it will be obstructed to impart a detennined curved peripheral edge in the first object of the present invention to the acrylic fiber.
  • the cross-sectional shape of the actually obtained fiber filament will be approximately circular and it will be difficult to form a microscopic form peculiarity of the cross-section of a fiber known as a so-called different shape cross-section fiber.
  • the fiber filament having passed through the coagulating bath is then subjected to a series of stretching steps defined by the relative formula (7), that is, the cold-stretching at the room temperature, the primary hot-stretching in hot water and further the secondary stretching in a steam heat medium.
  • these stretching steps the cold-stretching and primary hot-stretching give a substantial elongation to the fiber filament without destroying the skin-core structure formed mostly in the coagulating bath step, accelerate the orientation of the fiber forming components, give a required strength of the fiber filament and become factors of forming a proper curved shape defined by the relative formulas (1) and (2) in the peripheral edge part of the fiber filament.
  • the fiber filament subjected to the primary hotstretching is dried according to a normal process, is then led into a steam heat medium and is subjected to the secondary stretching.
  • Such secondary stretching is to further stretch the fiber filament having the curved peripheral edge shape formed by a series of steps from the coagulating bath to the primary stretching in hot water so that a desirable 60-degree mirrorsurface luster degree and contrast index may be imparted to the finally obtained acrylic fiber.
  • acrylic esters as methyl acrylate and ethyl acrylate
  • methacrylic esters as methyl methacrylate and ethyl methacrylate
  • carboxylic vinyl esters as vinyl formate and vinyl acetate
  • styrene a-methylstyrene
  • vinyl chloride vinylidene chloride
  • methacrylonitrile such amides as acrylamide, methacrylamide and a-methylene gretalamide and their N-substituted derivatives
  • unsaturated monoand dicharboxylic acids as acrylic acid, methacrylic acid, itaconic acid and maleic acid and their salts
  • unsaturated sulfonic acids as allylsulfonic acid, methallylsulfonic acid and styrene sulfonic acid and such unsaturated mono
  • aqueous solution of inorganic salts to be used as solvents and coagulating solutions inthe present invention there can be mentioned aqueous solutions of such thiocyanates as sodium thiocyanate, potassium thiocyanate, calcium thiocyanate and ammonium thiocyanate.
  • thiocyanates sodium thiocyanate, potassium thiocyanate, calcium thiocyanate and ammonium thiocyanate.
  • salts as zinc chloride, calcium chloride, sodium perchlorate and potassium perchlorate can be also used.
  • the present invention has disclosed that the brightness of an acrylic fiber by a wet-spinning system can be determined by the correspondence of the qualitative and quantitative levels of the brightness based on the macroscopic and microscopic form peculiarities of the cross-section of the fiber and a concrete means of imparting such peculiar cross-sectional shape and brightness to acrylic fibers and is a very significant finding in which the brightness which has been rather argued only as a characteristic of synthetic fibers by a wet spinning system is systematized so as to be applicable even to the improvement of the quantitative and qualitative evaluations of acrylic synthetic fibers by a melt-spinning system having a peculiar cross-sectional shape. Further, as an additional effect of the present invention, there can be mentioned the improvement of the. touch and bulkiness based on the form peculiarity of the fiber cross-section.
  • EXAMPLE 1 Two kinds of spinning solutions of a copolymer concentration of 11.3 percent and NaSCN concentration of 37 percent prepared by respectively dissolving in a concentrated aqueous solution of NaSCN a copolymer made by copolymerizing acrylonitrile, methyl acrylate and sodium methallylsulfonate at a ratio of 91/8.73/0.27 and a copolymer made by copolymerizing acrylonitrile and vinyl acetate at a ratio of 89/11 as acrylic fiber forming components were heated to a temperature of C. and were delivered into a coagulating bath consisting of an aqueous solution of 12 NaSCN at a temperature of 3 C. by using a spinnerette having the below mentioned cross-sectional shape.
  • a spinning device there was used a gold-platinum spinnerette in which were made 50 Y-shaped orifices in each of which three rectangular slots were radially arranged so that the phase difference might be 120 degrees,the length from the center of the crossing zones of the radial slots to the end of the slot in the lengthwise direction was 0.15 mm. and the width of the slot was 0.003 mm.
  • the value of the delivery ratio of said spinning solution in the coagulating bath was made 1.8.
  • the final spinning velocity through the outlet of the steam stretching machine was made 140 m./min.
  • the spun fiber filament was subjected to the coagulation in the coagulating bath, cold-stretching at the room temperature, water-washing, primary hot-stretching in boiling water, drying under the temperature conditions of a dry-bulb temperature of C. and wet-bulb temperature of 70 C., collapsing, secondary stretching by steam heat at C., relaxing heat-treatment in a steam atmosphere at 127 C. and drying treatment under a dry-heating action at 105 C. to make an acrylic fiber having a triangular cross-section.
  • spinnerettes there was used a spinnerette which was made of a polycarbonate and in which were made 3108 spinning orifices having the same opening shape as in Example 1 and a spinnerette of the same material in which were made 15,000 circular openings of a diameter of 0.095 mm.
  • An acrylic fiber of 3 deniers was made according to all the same steps as in Example 1 except that the spinning solution delivery ratio and stretching ratios were varied respectively as shown in Table 4.
  • the physical properties of the obtained fibers are also mentioned in Table perature, primary hot-stretching in hot water and secondary stretching in a steam heat medium, consecutively, such that 16X, 2.5X 3X, 31 wherein X, is the cold-stretching ratio at room temperature, X is the primary hot-stretching ratio in hot water and X is the secondarystretching ratio in the steam heat medium 2.
  • a process for producing acrylic fibers with improved cross-section of the fiber which edge is defined by the relative brightness which comprises extruding a spinning solution o u through essentially Y-shaped spinning orifices into a coagulatm 1 1 ing bath at a temperature of l0 to 15C., the inorganic salt Z and T 8 (1) concentration in the spinning solution and coagulating bath p p being in the range of fl fi and l 16 35 5 549 d
  • a is the minimum curve 47- height in microns of the peripheral edge measured in the direction vertical to the straight line connecting the two apexes of the triangular cross-section
  • p rs the minimum curve pitch length in microns of the peripheral edge measured in the respectively
  • the acrylic fiber according to claim 2 wherein the conthe spinning solution through the spinning orifice/the pull-out trast index Of the fiber is 15-50 and the 60-degree mirror-survelocity of the coagulated filament, within the range of 0.5 to f c lus er egree of the fiber is at least 35. 3.0, subjecting the filament to cold-stretching at room tem-

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  • Textile Engineering (AREA)
  • Mechanical Engineering (AREA)
  • Health & Medical Sciences (AREA)
  • Toxicology (AREA)
  • Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Artificial Filaments (AREA)
  • Spinning Methods And Devices For Manufacturing Artificial Fibers (AREA)
US7858A 1969-02-03 1970-02-02 Acrylic fibers with improved brightness and process for producing the same Expired - Lifetime US3673053A (en)

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JP836669A JPS5317690B1 (fr) 1969-02-03 1969-02-03

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US (1) US3673053A (fr)
JP (1) JPS5317690B1 (fr)
AT (1) AT313460B (fr)
BE (1) BE745336A (fr)
BR (1) BR7016543D0 (fr)
CA (1) CA937723A (fr)
CH (1) CH519040A (fr)
ES (1) ES376098A1 (fr)
FR (1) FR2033847A5 (fr)
GB (1) GB1287518A (fr)
IL (1) IL33801A (fr)
LU (1) LU60286A1 (fr)
NL (1) NL7001452A (fr)
SE (1) SE357773B (fr)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3885013A (en) * 1972-03-21 1975-05-20 Japan Exlan Co Ltd Method for producing acrylic synthetic fibers
US3976737A (en) * 1972-09-14 1976-08-24 Japan Exlan Company Limited Process for producing high shrinking acrylic fiber
US5387469A (en) * 1992-10-27 1995-02-07 Basf Corporation Multilobal fiber with projections on each lobe for carpet yarns

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB2018188A (en) * 1978-04-06 1979-10-17 American Cyanamid Co Wet spinning process for acrylonitrile polymer fiber

Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2777751A (en) * 1951-03-08 1957-01-15 American Cyanamid Co Process for spinning aqueous-saline solutions of acrylonitrile polymers
US2948581A (en) * 1955-12-20 1960-08-09 American Cyanamid Co Method of producing a synthetic fiber
US3194002A (en) * 1962-07-25 1965-07-13 Eastman Kodak Co Multifilament yarn of non-regular cross section
US3384694A (en) * 1963-11-21 1968-05-21 Asahi Chemical Ind Method of producing aligned acrylonitrile polymer filament yarns
US3491179A (en) * 1967-01-03 1970-01-20 American Cyanamid Co Preparation of acrylonitrile polymer fibers
US3523150A (en) * 1966-12-12 1970-08-04 Monsanto Co Manufacture of industrial acrylic fibers

Patent Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2777751A (en) * 1951-03-08 1957-01-15 American Cyanamid Co Process for spinning aqueous-saline solutions of acrylonitrile polymers
US2948581A (en) * 1955-12-20 1960-08-09 American Cyanamid Co Method of producing a synthetic fiber
US3194002A (en) * 1962-07-25 1965-07-13 Eastman Kodak Co Multifilament yarn of non-regular cross section
US3384694A (en) * 1963-11-21 1968-05-21 Asahi Chemical Ind Method of producing aligned acrylonitrile polymer filament yarns
US3523150A (en) * 1966-12-12 1970-08-04 Monsanto Co Manufacture of industrial acrylic fibers
US3491179A (en) * 1967-01-03 1970-01-20 American Cyanamid Co Preparation of acrylonitrile polymer fibers

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3885013A (en) * 1972-03-21 1975-05-20 Japan Exlan Co Ltd Method for producing acrylic synthetic fibers
US3976737A (en) * 1972-09-14 1976-08-24 Japan Exlan Company Limited Process for producing high shrinking acrylic fiber
US5387469A (en) * 1992-10-27 1995-02-07 Basf Corporation Multilobal fiber with projections on each lobe for carpet yarns

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DE2004809B2 (de) 1977-05-26
BE745336A (fr) 1970-08-03
SE357773B (fr) 1973-07-09
ES376098A1 (es) 1972-03-16
CA937723A (en) 1973-12-04
GB1287518A (en) 1972-08-31
CH519040A (de) 1972-02-15
AT313460B (de) 1974-02-25
DE2004809A1 (de) 1970-08-06
IL33801A (en) 1973-03-30
JPS5317690B1 (fr) 1978-06-10
NL7001452A (fr) 1970-08-05
FR2033847A5 (fr) 1970-12-04
LU60286A1 (fr) 1970-04-02
BR7016543D0 (pt) 1973-01-11
IL33801A0 (en) 1970-03-22

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