EP0010764B1 - Polypropylene yarn product of improved stability and method for preparing a textile material - Google Patents

Polypropylene yarn product of improved stability and method for preparing a textile material Download PDF

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Publication number
EP0010764B1
EP0010764B1 EP79104267A EP79104267A EP0010764B1 EP 0010764 B1 EP0010764 B1 EP 0010764B1 EP 79104267 A EP79104267 A EP 79104267A EP 79104267 A EP79104267 A EP 79104267A EP 0010764 B1 EP0010764 B1 EP 0010764B1
Authority
EP
European Patent Office
Prior art keywords
product
ethoxylated
polypropylene
yarn
phosphate ester
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.)
Expired
Application number
EP79104267A
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German (de)
English (en)
French (fr)
Other versions
EP0010764A3 (en
EP0010764A2 (en
Inventor
Peter Anthony Taylor
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.)
Phillips Petroleum Co
Original Assignee
Phillips Petroleum Co
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 Phillips Petroleum Co filed Critical Phillips Petroleum Co
Publication of EP0010764A2 publication Critical patent/EP0010764A2/en
Publication of EP0010764A3 publication Critical patent/EP0010764A3/en
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Publication of EP0010764B1 publication Critical patent/EP0010764B1/en
Expired legal-status Critical Current

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Classifications

    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M16/00—Biochemical treatment of fibres, threads, yarns, fabrics, or fibrous goods made from such materials, e.g. enzymatic
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M13/00—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment
    • D06M13/10—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with compounds containing oxygen
    • D06M13/144—Alcohols; Metal alcoholates
    • D06M13/148—Polyalcohols, e.g. glycerol or glucose
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M13/00—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment
    • D06M13/244—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with compounds containing sulfur or phosphorus
    • D06M13/282—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with compounds containing sulfur or phosphorus with compounds containing phosphorus
    • D06M13/292—Mono-, di- or triesters of phosphoric or phosphorous acids; Salts thereof
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M7/00—Treating fibres, threads, yarns, fabrics, or fibrous goods made of other substances with subsequent freeing of the treated goods from the treating medium, e.g. swelling, e.g. polyolefins
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M2200/00—Functionality of the treatment composition and/or properties imparted to the textile material
    • D06M2200/40—Reduced friction resistance, lubricant properties; Sizing compositions

Definitions

  • finishing compositions In the formation of textile materials from melt spun polypropylene it is normally necessary to apply a finishing composition to the filaments, yarns and other textile embodiments thereof to make such materials more amenable to the various operations to which they are subjected during processing, for example, spinning, winding, yarn-forming, weaving or knitting, and to improve the properties of the finish products.
  • the finishing composition In the processing of the textile materials, the finishing composition is intended to reduce friction between the yarn and various pieces of equipment with which it comes into contact, such as guides, rollers and the like, and in both the processing and use of the textile materials to reduce friction between the fibers themselves, to prevent fiber and yarn breakage and to minimize excessive attraction or repulsion of the filaments caused by electrostatic charges. Accordingly, such finishing compositions usually contain a lubricant and an antistatic agent. Various other additives such as bactericides or corrosion inhibitors, may also be added to the finishing composition.
  • thermoplastic materials respond to finishing compositions in the same manner, not all combinations of finishing agents are compatible with one another and not all finishing agents are compatible with stabilizers added to the thermoplastic melt.
  • ethoxylated lubricants have heretofore been found to be highly superior to conventional textile lubricants when utilized in finish compositions for treating melt spun polypropylenes. Accordingly, it is highly desirable to utilize these synthetic lubricants in the finish composition.
  • polypropylenes do not respond to ethoxylated lubricants in the same manner as other thermoplastic fiber-forming materials, when they contain a stabilizer system comprising a hindered phenol in an amount of from 0.1 to 0.6 weight percent total stabilizers, i.e. less than the normal amounts of stabilizers. Rather, it has been found that some antagonistic reaction occurs between an ethoxylated lubricant and the hindered phenol which results in decreasing the thermal, light and/or color stability of the polypropylene textile products.
  • the invention relates to a polypropylene yarn product of a melt spun polypropylene formed from a melt containing from 0.1 to 0.6 weight percent total stabilizer including a hindered phenol, and having applied thereto a finish composition comprising an ethoxylated textile lubricant and an antistatic agent, which is characterized in that said antistatic agent is a phosphate ester.
  • the invention relates to a process for preparing a polypropylene textile material comprising (a) melt spinning polypropylene filaments from a melt containing from 0.1 to 0.6 weight percent total stabilizer including a hindered phenol and (b) applying to said melt spun polypropylene a finish composition comprising an ethoxylated textile lubricant and a phosphate ester.
  • the yarn may also be draw-twisted before or after the packaging of the yarn.
  • Such draw-twisted yarns may be woven into products particularly suitable for use as dye bags, laundry bags, and the like.
  • the stability of polypropylene textile materials can be substantially improved. It has also been found that, in many cases, the color stability of such polypropylene textile materials can also be improved by the specified combination of ethoxylated lubricant and antistatic agent.
  • the finish composition optionally, but desirably, contains minor amounts of a bactericide and may also contain minor amounts of other additives such as corrosion inhibitors and the like.
  • finish composition may be applied to the textile materials at any time during the processing thereof, it is preferably applied to the filaments as soon as they have set, so that the full benefit of the stabilizing properties thereof can be realized during the later processing thereof.
  • as-spun polypropylene yarns of highly improved thermal stability and in many cases of improved light and/or color stability.
  • the yarns thus produced are draw-twisted and again packaged.
  • the draw-twisting can also be applied in a continuous process prior to the initial winding or packaging of the yarn.
  • the draw-twisted yarns have been found to be highly effective for the production of dye bags, laundry bags and the like when woven and formed into appropriate articles.
  • the polypropylene textile materials to which the present invention is directed are homopolymers of propylene and copolymers of propylene and another aliphatic 1-olefin containing 2 to 8 carbon atoms, in which the comonomer constitutes up to about 20 mole percent of the copolymer.
  • the ethoxylated textile lubricants utilized in accordance with the present invention include any of the known ethoxylated lubricants such as polyethylene glycols, mixed polyethylene-propylene glycols, monoalkyl esters of mixed polyethylene-polypropylene glycols, ethoxylated esters of fatty acids, rosin acids and tall oil acids, ethoxylated castor oils or ethoxylated hydrogenated castor oils.
  • More specific examples are ethoxylated aliphatic alcohols, ethoxylated alkylphenols, ethoxylated sorbitan (anhydro- sorbitol) esters, ethoxylated sorbitol esters, ethoxylated glycerol esters, ethoxylated pentaerythritol esters, ethoxylated fatty acids, ethoxylated fatty acid amides, ethoxylated-propoxylated fatty acids, ethoxylated-propoxylated fatty acid esters, ethoxylated-propoxylated castor oils, ethoxylated-propoxylated hydrogenated castor oils, ethoxylated-propoxylated aliphatic alcohols and ethoxylated-propoxylated alkyl phenols.
  • Presently preferred ethoxylated lubricants include the random copolymers of the monobutyl ether of poly(oxyethylene-oxy-1,2-propylene) having viscosities in terms of Saybolt Universal Seconds (SUS) at 100°F (38°C) ranging from 170 to 5100 and even more preferably from 250 to 3500, the methyl ether of poly(oxyethylene-oxy-1,2-propylene) laurate wherein the number of moles of combined ethylene oxide, is about 7 and the number of moles of combined propylene oxide is about 2, and the isododecyl ether/poly(oxyethylene) adduct wherein the number of moles of combined ethylene oxide is about 6 per mole hydrophobe.
  • SUS Saybolt Universal Seconds
  • the hindered phenols are utilized as thermal stabilizers or antioxidants. Such materials are known in the art.
  • Typical of such stabilizers are 2,6-di-t-butyl-4-methylphenol (BHT); octadecyl [3-(3,5-di-t-butyl-4-hydroxyphenyl)] propionate (irganox (TM) 1076, Ciba-Geigy Chemical Co.); tetrakis[methylene(3,5-di-t-butyl-4-hydroxyhydrocinnamate)] methane (Irganox (TM) 1010, Ciba-Geigy Chemical Co.), di-n-octadecyl(3,5-di-t-butyl-4-hydroxybenzyl)phosphonate; 1,3,5-trimethyl-2,4,6-tris(3,5-di-t-butyl-4-hydroxybenzyl) benzene and tris(3,5-di-t-butyihydroxybenzy))isocyanurate.
  • BHT 2,6-di-
  • the phosphate ester antistatic agent utilized in accordance with the present invention includes hydrocarbyl phosphate esters, ethoxylated hydrocarbyl phosphate esters, partially hydrolyzed hydrocarbyl phosphate esters or their salts.
  • hydrocarbyl is meant a hydrocarbon radical selected from the alkyl, cycloalkyl, aryl and combinations thereof such as alkyllauryl, containing from 1 to 20 C atoms.
  • Usually a mixture of di- and monoalkyl esters is utilized but the composition is also effective when completely esterified phosphoric acid compounds are employed. It has also been found that the use of these phosphate esters is quite effective in inhibiting color formation during gas fired heat treatments.
  • the inhibition of color formation is influenced by the pH and the neutralizing cations employed.
  • the pH is maintained between 3 and 9 and preferably between 4 and 7.
  • the preferred phosphate esters are the partially neutralized acid esters of phosphoric acid or the equivalent partially hydrolyzed triesters of phosphoric acid.
  • the present order of neutralizing cations has been found to be ammonium, mono-, di-and triethanolammonium, lithium, sodium and potassium. The potassium was found to be the least desirable, although useable in accordance with the present invention.
  • the finish composition of the present invention also desirably contains a bactericide such as 6-acetoxy-2,4-dimethyl-m-dioxane (Givgard DXN@, Givuadan Corp., Clifton, NJ).
  • a bactericide such as 6-acetoxy-2,4-dimethyl-m-dioxane (Givgard DXN@, Givuadan Corp., Clifton, NJ).
  • the ethoxylated lubricant is utilized in amounts between 50 and 98 percent by weight of the finish composition, preferably between 60 and 95 percent by weight of the composition.
  • the balance of the finish composition is preferably the antistatic agent which is used in amounts between 2 and 50 percent by weight, preferably between 5 and 40 percent by weight of the finish composition.
  • the bactericide may be present in amounts up to about 1.0 percent by weight of the final composition and like minor amounts of other suitable additives may be included, such as corrosion inhibitors.
  • the polypropylene melt is extruded from a plural orifice spinneret 2, of conventional design. While spinneret 2 is shown in the drawings as producing a single threadline it is obvious that the spinneret may produce two or more threadlines.
  • the filaments from spinneret 2 are passed through a conventional quench zone 4 where the filaments are cooled and set. Finish is applied by conventional finish applicator means 6 which may take any appropriate form. For example, a "kiss" roll may be utilized to apply finish to the filaments as a gathered threadline or yarn or as a band spread across the finish roll.
  • a slot type finish applicator could also be utilized, the only requirement being that the finish be uniformly applied to the filaments or yarn.
  • the yarn is then wound on an appropriate conventional winder 8 to form a yarn package 10.
  • Appropriate guides, guide rolls, godet rolls, and the like will of course be utilized.
  • the process as illustrated in Figure 1 produces a yarn in its as-spun state.
  • draw-twist the yarn before winding the same on package 10.
  • Whether draw-twisting is practiced as a part of the spinning operation will depend to some extent upon whether the yarn is partially oriented yarn or a conventional undrawn yarn. Normally it is considered that winder takeup speeds in excess of about 1500 meters per minute will produce a partially oriented yarn whereas takeup speeds of less than about 1500 meters per minute, for example about 800 meters per minute, produce an unoriented or undrawn yarn.
  • Figure 2 illustrates a preferred draw-twisting operation in accordance with the present invention.
  • yarn is withdrawn from yarn package 10 by means of the draw means 12 made up of conventional draw rolls, 12a and 12b, respectively.
  • twist means 14 conventionally applies by means of a flyer 16 as it is wound on package 18.
  • any appropriate drawing and twisting apparatus may be utilized. It will also be apparent to one skilled in the art that the system would include appropriate guides, guide rolls, draw heaters, etc.
  • the draw-twisted yarn when converted into an appropriate fabric and formed into a bag or the like has been found to make excellent dye bags, laundry bags and the like.
  • the resultant products have superior temperature stability compared with conventionally finished textile materials of polypropylene and to conventional dye bag textiles.
  • certain of the polypropylenes have been found to have superior inhibition to color formation as compared with conventionally finished polypropylenes and commercially available dye bag textiles.
  • a polypropylene melt composition was prepared by adding to the polypropylene 0.05 parts by weight per 100 parts of polypropylene (phr) of calcium stearate, 0.3 phr tris(3,5-di-t-butyl- hydroxybenzyl)isocyanurate, 0.1 phr hydrolysis resistant distearyl pentaerythritol disphosphite, 0.1 phr trilauryl trithiophosphite and about 0.375% titanium oxide.
  • the polypropylene had a melt flow of 12 and when combined with the specified stabilizing system is designated hereinafter as resin B.
  • finish I contains the following:
  • the finished designated as finish II contains the following:
  • the specified finishes were applied to the yarns at a rate of 3.6 to 4.5 weight % solids based on the weight of yarn.
  • the yarn was knitted into a sleeve and the sleeve trimmed so that the yarn could be easily unravelled for sampling.
  • the sleeve weighing about 5 grams, was placed in a 500 milliliter, flat bottom flask fitted with a water cooled reflux condenser. 200 milliliters of a 0.2% AATCC Standard Soap Solution was boiled under reflux for 6 hours after which time the sleeve was removed, rinsed free from the solution and squeezed dry. The sleeve was then dried for 15 hours at 130°C in an electrically heated, forced air oven to complete the cycle. About a 5 foot (1.5 m) sample of the yarn was removed from the sleeve and tested for strength and elongation retention on an Instron Tensile Tester after 3, 5 and 8 cycles, respectively.
  • the ultraviolet stability was measured by exposing 2" by 3" (5.1 by 7.6 cm) knitted sleeves mounted on black backed Atlas mounting fadeometer cards. Degradation is either when the fabric tears or when the fabric flakes while being gently scratched with a fingernail. Usually if the sleeve is of fine denier yarn the fabric will tear and it is the sleeve surface closest to the black backing which tears before the surface closest to the arc. With heavier denier fabrics flaking of the surface facing the arc usually occurs before the fabric can be torn. Table 2 below gives the results of these tests.
  • finishes containing an ethoxylated lubricant and the phosphate-type antistatic agents, in accordance with the present invention were vastly superior to finishes containing only ethoxylated lubricants and balanced finishes containing the ethoxylated lubricants and antistatic agents other than the phosphate-type antistatic agents utilized in accordance with the present invention, which other lubricant compositions have been highly successful as finishes for other textile materials.
  • finish compositions of the present invention were tested for use as dye bag yarns.
  • the yarns were made from a stabilized polypropylene melt designated resin B in Example 1 and were finished with either finishes I or II as specified in the previous examples.
  • the finish was metered onto the yarn with no problems.
  • the yarn was draw-twisted using a standard 1680/280 yarn process. Eight positions of a draw twister processing 1680/280 yarns were used. Again no problems were seen.
  • the yarns were then coned into ten ounce (280 g) packages and knitted into dye bags for testing.
  • the mock dye cycle test is the same as the previously described laundering cycle except that the treating solution was 200 milliliters of the following:
  • the GMC-Arc fadeometer exposure test was substantially the same as the previously described carbon arc fadeometer test.
  • the accelerated gas fade color development test simulates processes which involve heating and curing or drying in gas fired ovens. It also produces colors which have been seen transiently under the same kinds of storage conditions which have not heretofore been simulated.
  • the test provides for a 10 minute heating cycle at 130°C followed by a 2-hour treatment in an atmospheric fume chamber (AATCC test method 23-1975).
  • the regular gas fade test is described in AATCC test method 23-1975.
  • the toughness is defined as:
  • the toughness factor is used as the critical criterion because it balances the elongation and the tenacity into a property which has been found to be the equivalent to performance in actual practice.
  • the dye bag yarns in accordance with the present invention are whiter than the control yarn and than the commercial dye bag yarn; it remains whiter in the cycling test, the thermal stability tests and in actual laboratory storage experiments. Accelerated gas fade tests showed no pinking problems with the dye bag yarns of the present invention and no such problems have been observed with the control yarns. In 3-cycle gas fade tests, the yarns show quite a severe color development. However, this is not believed to be a problem in dye bag yarns since the only place it will slow up is after long storage in a high nitrogen oxide atmosphere. The dye bag yarns would not be subjected to such an environment since legislation has essentially ruled out this kind of contamination.
  • Tests were also conducted utilizing a 12 melt flow polypropylene melt composition stabilized with 0.30% distearylthiodipropionate, 0.10% tetrakis[methylene(3,5-di-t-butyl-4-hydroxy hydrocinnimate)] methane and 0.05% calcium stearate and a 12 melt flow polypropylene having a stabilizer system; comprising, 0.30% distearylthiodipropionate, 0.10% tetrakis[methylene13,5-di-t-butyl-4-hydroxy hydrocinnimate)] methane (Irganox(TMI 1010, Ciba-Geigy), 0.05% calcium stearate and 0.10% hydrolysis resistant distearyl pentaerythritol diphosphate Weston (TM) 619, a product of Borg-Warner Chemicals, Parkersburg, W.
  • TM distearyl pentaerythritol diphosphate
  • the finish compositions of the present invention contains a hindered phenol. Specifically, inhibition of color formation during gas fired heat treatments is improved. For example, yarns spun from resin formulations B and C above when heated to 130°C and exposed for 2 hours in a nitrogen oxide gas fade oven will turn pink. This pink color will be increased in the presence of an ethoxylated textile lubricant-containing finish unless the finish has added thereto a phosphate type antistatic agent as taught in the present invention.

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  • Engineering & Computer Science (AREA)
  • Textile Engineering (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • General Chemical & Material Sciences (AREA)
  • Microbiology (AREA)
  • Biochemistry (AREA)
  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Emergency Medicine (AREA)
  • Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
  • Artificial Filaments (AREA)
  • Materials For Medical Uses (AREA)
EP79104267A 1978-11-06 1979-11-02 Polypropylene yarn product of improved stability and method for preparing a textile material Expired EP0010764B1 (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US95778678A 1978-11-06 1978-11-06
US957786 1978-11-06

Publications (3)

Publication Number Publication Date
EP0010764A2 EP0010764A2 (en) 1980-05-14
EP0010764A3 EP0010764A3 (en) 1981-03-25
EP0010764B1 true EP0010764B1 (en) 1984-02-01

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Application Number Title Priority Date Filing Date
EP79104267A Expired EP0010764B1 (en) 1978-11-06 1979-11-02 Polypropylene yarn product of improved stability and method for preparing a textile material

Country Status (7)

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EP (1) EP0010764B1 (es)
JP (1) JPS5567073A (es)
AU (1) AU518276B2 (es)
CA (1) CA1150008A (es)
DE (1) DE2966622D1 (es)
ES (1) ES485683A0 (es)
NO (1) NO793299L (es)

Families Citing this family (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4291093A (en) * 1979-10-05 1981-09-22 Phillips Petroleum Co. Stabilized polyolefin substrate overcoated with an ethoxylated lubricant and a phosphate ester
JPS6485365A (en) * 1987-09-22 1989-03-30 Chisso Corp Dyeable polypropylene fiber for clothing
USRE35621E (en) * 1989-05-30 1997-10-07 Hercules Incorporated Cardable hydrophobic polypropylene fiber, material and method for preparation thereof
IE903679A1 (en) * 1989-10-16 1991-04-24 Du Pont Aramid fibres with deposit-free finish
TR24601A (tr) * 1990-10-16 1992-01-01 Du Pont Tortusuz apreli aramid elyaf
DE69120209T2 (de) * 1990-11-15 1996-10-24 Hercules Inc Kardierbare hydrophobe Polyolefinfaser, Material und Verfahren zu ihrer Herstellung
CA2069269C (en) * 1991-05-28 1998-09-15 Roger W. Johnson Cardable hydrophobic polypropylene fiber
US5545481A (en) * 1992-02-14 1996-08-13 Hercules Incorporated Polyolefin fiber
BE1023475B1 (nl) * 2016-06-09 2017-04-03 Vertexco Nv Werkwijze voor het vervaardigen van een spinolie

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB1118878A (en) * 1965-01-19 1968-07-03 Ici Ltd Modifying shaped synthetic fibre forming polymer articles
US3619274A (en) * 1967-04-21 1971-11-09 Du Pont Coated synthetic material
JPS5247079A (en) * 1975-10-13 1977-04-14 Kureha Chem Ind Co Ltd Biaxially oriented three-layered films with gas barrier properties

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Publication number Publication date
DE2966622D1 (en) 1984-03-08
AU5233679A (en) 1980-05-15
CA1150008A (en) 1983-07-19
EP0010764A3 (en) 1981-03-25
NO793299L (no) 1980-05-07
ES8200730A1 (es) 1981-11-16
ES485683A0 (es) 1981-11-16
JPS5567073A (en) 1980-05-20
AU518276B2 (en) 1981-09-24
EP0010764A2 (en) 1980-05-14

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