US3877871A - Process for rendering wool non-felting - Google Patents

Process for rendering wool non-felting Download PDF

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Publication number
US3877871A
US3877871A US296473A US29647372A US3877871A US 3877871 A US3877871 A US 3877871A US 296473 A US296473 A US 296473A US 29647372 A US29647372 A US 29647372A US 3877871 A US3877871 A US 3877871A
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United States
Prior art keywords
reaction product
epoxide
process according
groups
amine
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Expired - Lifetime
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US296473A
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English (en)
Inventor
Heinz Abel
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Novartis AG
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Ciba Geigy AG
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Filing date
Publication date
Priority to BE758703D priority Critical patent/BE758703A/xx
Priority to CH1665769D priority patent/CH1665769A4/xx
Priority to CH1665769A priority patent/CH524010A/de
Priority to DE19702054173 priority patent/DE2054173A1/de
Priority to CA097,333A priority patent/CA943307A/en
Priority to AT1005470A priority patent/AT305944B/de
Priority to FR7040156A priority patent/FR2067066B1/fr
Priority to NL7016376A priority patent/NL7016376A/xx
Priority to GB53235/70A priority patent/GB1284684A/en
Application filed by Ciba Geigy AG filed Critical Ciba Geigy AG
Priority to US296473A priority patent/US3877871A/en
Application granted granted Critical
Publication of US3877871A publication Critical patent/US3877871A/en
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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
    • 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
    • D06M13/322—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 nitrogen
    • D06M13/35—Heterocyclic compounds
    • D06M13/355—Heterocyclic compounds having six-membered heterocyclic rings
    • D06M13/358—Triazines
    • D06M13/364—Cyanuric acid; Isocyanuric acid; Derivatives thereof
    • 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
    • C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
    • C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
    • C08G59/40—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the curing agents used
    • C08G59/50—Amines
    • C08G59/56—Amines together with other curing agents
    • C08G59/58—Amines together with other curing agents with polycarboxylic acids or with anhydrides, halides, or low-molecular-weight esters thereof

Definitions

  • the subject of the invention is a process for rendering wool non-felting by the exhaustion process, using synthetic resins having an affinity for the wool fibre, characterized in that before the non-felting finishing with the synthetic resins, the wool is treated with an aqueous preparation which contains 0.1 to 2 percent by weight of dichlorisocyanuric acid or of an alkali metal salt thereof, relative to the weight of the wool to be treated.
  • Preferred synthetic resins with affinity for the wool fibre, for rendering wool non-felting are here 1 reaction products of basic polyamides with epoxides, alkyl ethers of aminoplast precondensates, polyfunctional compounds or epoxide-aminoplastalkyl ether reaction products, or (2) reaction products of epoxideamine reaction products with epoxides, or (3) epoxidepolycarboxylic acid reaction products with amines or amine-epoxide reaction products.
  • the aqueous preparation contains 0.5 to 1 percent by weight of dichloroisocyanuric acid or of an alkali salt thereof, relative to the weight of the wool to be treated.
  • the alkali metal salts of dichloroisocyanuric acid are preferred to the free acid.
  • the pretreatment of the wool is, as a rule, carried out at a temperature of 20 to 50C.
  • reaction products (1), (2) and (3) used as preferred synthetic resins for the process according to the invention are especially the following products:
  • Reaction products 1 1.1 Reaction product of (a) basic polyamides which are obtained by condensation of (a') polymeric, preferably dimeric to trimeric, unsaturated fatty acids and (b') polyalkylenepolyamines, and of (b) epoxides, withv the equivalent ratio of the amino groups of the component (a) to the epoxide groups of the component (b) being 1:1 to 5:1, and the reaction is carried out in the presence of organic solvents with temperatures of at most 80C, and steps are taken, not later than on completion of the reaction, that a sample of the reaction mixture, after addition of water, has a pH value of 2 to 8 by virtue of addition of acid.
  • Reaction product of (a) basic polyamides which are obtained by condensation of (a') polymeric, preferably dimeric to trimeric, unsaturated fatty acids and (b') polyalkylenepolyamines, and of (b) polyfunctional, preferably difunctional, compounds which possess, as functional groups or atoms, mobile halogen atoms, vinyl, acid, ester, acid halide, acid anhydride or isocyanate groups or at most one epoxide group together with other functional groups or atoms of the nature indicated, with the equivalent ratio of the amino groups of the component (a) to the functional groups or atoms of the component (b) being 1:1 to 10:1, and the pH value of the reaction mixture of components (a) and (b) is adjusted to a value of 2 to 8 not later than on completion of the reaction.
  • Reaction products 2 2.1 Reaction product of (a) a reaction product of (a') a polyglycidyl ether, which is liquid at room temperature, of a polyphenol, and (b') a cycloaliphatic or cycloaliphaticaliphatic di-primary diamine in which at least one of the primary amino groups is bonded to a cycloaliphatic ring carbon atom, with the reaction being carried out in a ratio of 1 epoxide group equivalent to 3 to 5.5 amino group equivalents, in the absence of solvents, at temperatures of to C, and (b) an epoxide compound, with the reaction being carried out in a ratio of 1 epoxide group equivalent to 3 to 5 amino group equivalents at temperatures below 100C and steps aretaken through addition of acid, not later than on completion of the reaction, that a sample of the reaction mixture has a pH value of 2 to 7 after dilution with water.
  • Reaction products 3 3.1 Reaction product of (a) a reaction product of (a') an epoxide which contains at least two epoxide groups per molecule and (a") an organic carboxylic acid whichcontains at least 2 carboxyl groups per molecule, with the equivalent ratio of epoxide groups to acid groups being 1:0.1 to 1:0.8, with (b) (b') an amine containing at least two primary amino groups, wherein the amino groups each possess at least one hydrogen atom, bonded to nitrogen, or (b") .a reaction product of the component (b') with an epoxide which per molecule contains at least two epoxide groups, and wherein the equivalent ratio of hydrogen bonded to aminonitrogen to epoxide groups is 3:1 to 1 1:1, with the reaction being carried out in the presence of an organic solvent and-the equivalent ratio of epoxide groups to hydrogen bonded to aminenitrogen is 1:2 to 1:10, and steps are taken, through addition of acid, not later than on completion of the reaction, that
  • reaction product of (a) a reaction product of at least (a') one epoxide which contains at least two epoxide groups per molecule and-at least (a") one polymeric, unsaturated, preferably dimeric to trimeric, fatty-acid, with the equivalent ratio of epoxide groups to acid groups being 0.45:1 to 0.95:1 and (b) an amine containing at least two amino groups and exclusively basic nitrogen atoms, wherein the amino groups each possess at least one hydrogen atom bonded to nitrogen, or ammonia, with the reaction being carried out in the presence of an organic solvent at a temperature of to 120C and the equivalent ratio of acid groups to hydrogen bonded to aminenitrogen or to ammonia is 1:1 to 1:10, and steps are taken not later than on completion of the reaction, if appropriate through addition of a base, that a sample of the reaction mixture has a pH value of 7.5 to 12 after dilution with water.
  • reaction products 3.2 can optionally also further be obtainedby reaction with aliphatic or aromatic diisocyanates.
  • reaction product of (a) and (b) is reacted with the diisocyanate, or the component (a) is first reacted with the diisocyanate and then with (b).
  • n 1, 2 or 3, are preferably used as component (a).
  • epoxides are used, namely component (b) in reaction product 1.1, (a") in 1.4, (b) in 2.1, (a) in 3.1, in (b") in 3.1, and (a) in 3.2. 1
  • epoxides should contain at least 2 epoxide groups per molecule and should be in the monomolecular to at most slightly polymerised state, that is to say possess a high content of reactive epoxide groups, appropriately having an epoxide group equivalent of at most 1,000.
  • epoxides of epihalogenohydrins and so-called bisphenols,'such asfor example the reaction product of 2,2-bis-(4'-hydroxyphenyl)- propane with epichlorohydrin have here proved advantageous.
  • the component (b) for the manufacture of reaction products 1.3 can, for example, be a'phthalic aciclalkyl hydrogen atom bonded tohnitrogen. .
  • the component (b) for the manufacture of reaction products 1.3 can, for example, be a'phthalic aciclalkyl hydrogen atom bonded tohnitrogen.
  • amines can be piperazines or phenylamines or poly amines such as are used for the manufacture of component (a) in the reaction products (1).
  • cycloaliphatic amines such as are also used for the manufactureof the reaction products 2.1, there-may be mentioned diprimary cycloaliphatic diamines such as 3,5,5-trimethyl- 1 amino-3'aminomethyl-cyclohexane or aminomethyl-cyclopentane.
  • the procedurefollowed is that subsequent to the treatment with dichloroisocyanuric acid or its alkali salts, the woolis treated with aqueous preparations containing the synthetic resins, at temperatures of preferably to 100C.
  • the aqueous preparation of the synthetic resin can contain yet further additives such as wetting agents and dispersing agents. After impregnation with the synthetic resin preparation, the wool is dried and subjected to a treatment at elevated temperature.
  • a particularly advantageous process proves to be the process for dyeing wool and rendering it nonfelting in which, successively and in optional sequence, using the exhaustion method, the wool is on the one hand dyed and on the other hand treated with an aqueous solution of dichloroisocyanuric acid or its alkali salts, preferably at 30 to 50C, and is subsequently treated with the aqueous preparations of the synthetic resins at 35 to 100C, at pH values of 3 to 9 or of 6 to 1, depending on whether cationic or anionic synthetic resins are being used.
  • Dyeing and rendering non-felting can thus be com bined in a simple manner and carried out in the same ester, a halogenacetic acid alkyl ester, and alkylene di- 7 halide, an alkylenediisocyanate or an epihalogenohydrin.
  • the components (a) in the reaction products 3.l and 3.2 can be the same aliphatic ethylenically unsatu rated dimeric to trimeric fatty acids asare used for the manufacture of the basic polyamides in the case of the reaction products (1).
  • reaction product 3.1 possible very suitable components (a) for the reaction product 3.1 are also aliphatic dicarboxylic acids with .2 to 10 carbon atoms or aromatic dicarboxylic acids.
  • the amines (b) and (b) in the reaction products 3.1 and 3.2 are preferably aliphatic, cycloaliphatic, heterocyclic or aromatic amines which contain at least 2 amino groups, and wherein at least one amino group is primary and another amino group contains at least one.
  • Dyeing can here be carried out in the customary sulphuric acid, acetic acid, sodium sulphate, ammo-,
  • the liquor used for the non-felting treatment con tains, in addition to the preparation of the synthetic resin, the acid required to establish the acid medium.- 0
  • the process is preferably carried out in the weakly alkaline range of about pH 8 to 9, ammonia or salts which react alkaline, such asfor example trisodium phosphate, being added to the 1i 7 quor.
  • the liquors can also contain yet other customary additives such as agents for imparting a soft handle, or bleaching agents. Preferably, these agents are added to the preparation after absorption of the synthetic resin on the wool.
  • vent and water relative to the weight of wool, is appropriately 0.5 to 5 preferably 1.2 to 3
  • the process iscarried out at temperaturesof 3510 100C and in doing so, between 5 to 1-amino-2- minutes is in most cases required for an extensive to practically complete fixing of the synthetic resin.
  • the sequence of the two processes is optional; in general, it tends to be advantageous to dye first and carry out the non-felting treatment subsequently.
  • the combined process for dyeing wool and rendering it nonfelting is particularly well suited to actual machine dyeing, where the goods being dyed are static and the liquor is agitated.
  • parts and percentages denote parts by weight and percentages by weight.
  • the relationship of parts by volume to parts by weight is as of ml of g.
  • a highly viscous, clear product having an acid number of 64 and an epoxide group content of 0 is obtained.
  • 87 g of the product thus produced (0.1 acid equivalent) are dissolved in 87 g of n-butylglycol and after addition of 7.3 g of triethylenetetramine (0.3 amine equivalent) the whole is stirred for 1 hour at 60C. Thereafter 275 g of deionised water are added and the mixture is further stirred until cold.
  • a 20% strength solution having a pH value of 8.8 is obtained.
  • a pH value of 9.2 is established by adding 6 g of 24% strength ammonia.
  • the solids content of this product is about 10%.
  • a fresh treatment bath of 1,000 l of water at 40C is i then prepared.
  • 500 g of the sodium salt of dichloroisocyanuric acid are first added, followed after 10 minutes by 8,000 g of a preparation according to in--' struction F and 4,000 g of glacial acetic acid.
  • the resuiting emulsion is uniformly absorbed on the wool in 1 about 20 minutes.
  • 200 g of a condensation product of 1 mol of octadecyl alcohol. and 35 mols of ethylene oxide are still added, and after i a further 10 minutes the goods are rinsed and dried.
  • the yarn is non-felting according to IWS Specifications. 7B.
  • preparation F the preparations according to instructions A to E can also be used.
  • EXAMPLE 3 100 kg of wool hank yarn are first dyed in the usual manner withreactive dyestuffs.
  • a fresh treatment bath of 1 kg of the sodium salt of dichloroisocyanuric acid in 1,000 l of water is prepared and the wool is treated therein for 30 minutes, at 30C. Thereafter it is rinsed, and a bath consisting of 0.6 kg of sodium bicarbonate, 8 kg of the product according to instruction G, 0.5 kg of ammonia (25% strength) and 400 l of water is prepared. An emulsion forms in this bath and is completely absorbed on the wool over the course of to 30 minutes. Thereafter 2 kg of an approximately strength aqueous softener emulsion, containing a polyethylene which contains a few carboxyl groups, and a fatty amine, are added to the bath, and after 15 minutes the goods are rinsed twice and dried.
  • the wool yarn is non-felting according to lWS Specification 71.
  • preparation G instead of preparation G, the preparations according to instructions H to J can also be used.
  • a process for rendering wool non-felting comprising the steps of immersing the wool in an aqueous exhaustion bath which consists essentially ofa water solution of 0.1 to 2% by weight, relative to the weight of the wool to be treated, of dichloroisocyanuric acid or of an alkali metal salt thereof, and thereafter treating the wool in an exhaustion bath with an aqueous solution of 0.5 to 5% by weight relative to the weight of the wool to be treated of a synthetic resin, at a temperature of 35 to 100C, wherein the synthetic resin is the reaction product (a), (b) or (c), wherein (a) is the reaction product of a basic polyamide with an epoxide, or with an alkyl ether of an aminoplast precondensate, or with an epoxide-amino-plast-alkyl ether reaction product; (b) is a reaction product of an epoxide with an amineepoxide reaction product; and (c) is thereaction product of an epoxid
  • aqueous preparation contains 0.5 to l per cent by weight of dichloroisocyanuric acid or of an alkali metal salt thereof.
  • said basic polyamide comprises the reaction product of a polymeric unsaturated fatty acid with a polyalkylenepolyamine.
  • reaction product is a basic polyamide reacted with an epoxide, the equivalentratio of amine groups to epoxide groups being from 1:1 to 5:1 and the pH of the reaction product not later than on completion of the reaction is adjusted to 2 to 8.
  • reaction product is a basic polyamide reacted with the reaction product of l. 1.5 to 6 moles of an epoxide which contains at least 2 epoxide groups per molecule and 2. 1 mole of an aminoplast precondensate containing alkyl ether groups with the equivalent ratio of amino groups of polyamide to said epoxide aminoplast reaction product being 1:1 to 5:1.
  • reaction product is a basic polyamide reacted with the reaction product of l. 1.5 to 6 moles of an epoxide which contains at least 2 epoxide groups per molecule and 2. 1 mole of an aminoplast precondensate containing alkyl ether groups with the equivalent ratio of amino groups of polyamide to said epoxide aminoplast reaction product being 1:1 to 5:1.
  • aminoplast precondensate is a methylolated melamine containing 2 or 3 n-butyl ether groups.
  • synthetic resin (b) comprises the reaction product of l. 1 equivalent of an epoxide with 2. 3 to 5 equivalents of the reaction product of a. 1 equivalent of a polyglycidyl ether of a polyphenol that is normally liquid with b. 3 to 5.5 equivalents of a cycloaliphatic or cycloaliphatic-aliphatic di-primary amine in which at least one of the primary amino groups is bonded to a cycloaliphatic ring carbon atom.
  • synthetic resin (c) comprises the reaction product of 1. one equivalent of the reaction product of an epoxide containing at least 2 epoxide groups per molecule with an organic carboxylic acid which contains at least 2 carboxyl groups per molecule, the equivalent ratio of epoxide groups to acid groups being 120.1 to 110.8 with 2. 2 to 10 equivalents of hydrogen bonded to amine nitrogen of a. an amine containing at least 2 primary amino groups or b. the reaction product of an amine containing at least 2 primary amino groups with an epoxide containing at least 2 epoxide groups where the ratio of hydrogen. bonded to amine nitrogen to epoxide groups is 3:1 to 11:1.
  • synthetic resin (c) comprises the reaction product of 1. an epoxide containing at least 2 epoxide groups per molecule with a polymeric unsaturated fatty acid, the equivalent ratio of epoxide groups to acid groups is 0.45:1 to 0.95:1 with 2. an amine containing at least 2 amine groups, the

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  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Textile Engineering (AREA)
  • Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
  • Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)
  • Phenolic Resins Or Amino Resins (AREA)
US296473A 1969-11-10 1972-10-10 Process for rendering wool non-felting Expired - Lifetime US3877871A (en)

Priority Applications (10)

Application Number Priority Date Filing Date Title
BE758703D BE758703A (fr) 1969-11-10 Procede servant a rendre la laine infeutrable
CH1665769D CH1665769A4 (enrdf_load_stackoverflow) 1969-11-10 1969-11-10
CH1665769A CH524010A (de) 1969-11-10 1969-11-10 Verfahren zum Filzfestmachen von Wolle
CA097,333A CA943307A (en) 1969-11-10 1970-11-04 Process for rendering wool non-felting
DE19702054173 DE2054173A1 (de) 1969-11-10 1970-11-04 Verfahren zum Filzfestmachen von Wolle
AT1005470A AT305944B (de) 1969-11-10 1970-11-09 Verfahren zum Filzfestmachen von Wolle
FR7040156A FR2067066B1 (enrdf_load_stackoverflow) 1969-11-10 1970-11-09
NL7016376A NL7016376A (enrdf_load_stackoverflow) 1969-11-10 1970-11-09
GB53235/70A GB1284684A (en) 1969-11-10 1970-11-09 Process for rendering wool non-felting
US296473A US3877871A (en) 1969-11-10 1972-10-10 Process for rendering wool non-felting

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
CH1665769 1969-11-10
US8663270A 1970-11-03 1970-11-03
US296473A US3877871A (en) 1969-11-10 1972-10-10 Process for rendering wool non-felting

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US3877871A true US3877871A (en) 1975-04-15

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US296473A Expired - Lifetime US3877871A (en) 1969-11-10 1972-10-10 Process for rendering wool non-felting

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US (1) US3877871A (enrdf_load_stackoverflow)
AT (1) AT305944B (enrdf_load_stackoverflow)
BE (1) BE758703A (enrdf_load_stackoverflow)
CA (1) CA943307A (enrdf_load_stackoverflow)
CH (2) CH524010A (enrdf_load_stackoverflow)
DE (1) DE2054173A1 (enrdf_load_stackoverflow)
FR (1) FR2067066B1 (enrdf_load_stackoverflow)
GB (1) GB1284684A (enrdf_load_stackoverflow)
NL (1) NL7016376A (enrdf_load_stackoverflow)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4592757A (en) * 1984-05-10 1986-06-03 Basf Aktiengesellschaft Production of dyed or undyed wool with an antifelting finish: quaternized piperazine condensate
WO1996040815A1 (en) * 1995-06-07 1996-12-19 United Catalysts, Inc. Water-soluble aminoplast-ether copolymers

Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2992944A (en) * 1959-11-13 1961-07-18 Charles H Binkley Shrinkproofing wool with compositions containing a polyester
US2993747A (en) * 1955-02-18 1961-07-25 Monsanto Chemicals Shrinkproofing wool textiles with trichlorocyanuric acid or dichlorocyanuric acid and mixtures thereof
US3019076A (en) * 1958-07-22 1962-01-30 Jr Clay E Pardo Treatment of textiles with polyepoxides and polyamides
US3236585A (en) * 1962-09-05 1966-02-22 Prec Processes Textiles Ltd Process for reducing tendency of wool to felt
US3441435A (en) * 1964-04-08 1969-04-29 Bayer Ag Process and composition for imparting antistatic finish to textile materials
US3649575A (en) * 1969-04-10 1972-03-14 Ciba Ltd Stable preparations for finishing wool
US3681128A (en) * 1969-01-13 1972-08-01 Ciba Geigy Ag Process for finishing wool

Patent Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2993747A (en) * 1955-02-18 1961-07-25 Monsanto Chemicals Shrinkproofing wool textiles with trichlorocyanuric acid or dichlorocyanuric acid and mixtures thereof
US3019076A (en) * 1958-07-22 1962-01-30 Jr Clay E Pardo Treatment of textiles with polyepoxides and polyamides
US2992944A (en) * 1959-11-13 1961-07-18 Charles H Binkley Shrinkproofing wool with compositions containing a polyester
US3236585A (en) * 1962-09-05 1966-02-22 Prec Processes Textiles Ltd Process for reducing tendency of wool to felt
US3441435A (en) * 1964-04-08 1969-04-29 Bayer Ag Process and composition for imparting antistatic finish to textile materials
US3681128A (en) * 1969-01-13 1972-08-01 Ciba Geigy Ag Process for finishing wool
US3649575A (en) * 1969-04-10 1972-03-14 Ciba Ltd Stable preparations for finishing wool

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4592757A (en) * 1984-05-10 1986-06-03 Basf Aktiengesellschaft Production of dyed or undyed wool with an antifelting finish: quaternized piperazine condensate
WO1996040815A1 (en) * 1995-06-07 1996-12-19 United Catalysts, Inc. Water-soluble aminoplast-ether copolymers
AU721667B2 (en) * 1995-06-07 2000-07-13 Southern Clay Products Inc. Water soluble aminoplast-ether copolymers

Also Published As

Publication number Publication date
DE2054173A1 (de) 1971-05-19
CH1665769A4 (enrdf_load_stackoverflow) 1972-02-29
NL7016376A (enrdf_load_stackoverflow) 1971-05-12
FR2067066A1 (enrdf_load_stackoverflow) 1971-08-13
AT305944B (de) 1973-03-26
FR2067066B1 (enrdf_load_stackoverflow) 1976-03-19
CH524010A (de) 1972-06-15
CA943307A (en) 1974-03-12
GB1284684A (en) 1972-08-09
BE758703A (fr) 1971-05-10

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