US3714074A - Foam profile regulating composition and anionic detergent composition containing same and having inverse foam to temperature relationship - Google Patents

Foam profile regulating composition and anionic detergent composition containing same and having inverse foam to temperature relationship Download PDF

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US3714074A
US3714074A US00041359A US3714074DA US3714074A US 3714074 A US3714074 A US 3714074A US 00041359 A US00041359 A US 00041359A US 3714074D A US3714074D A US 3714074DA US 3714074 A US3714074 A US 3714074A
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composition according
fatty acid
percent
composition
polyethoxylated
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J Inamorato
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Colgate Palmolive Co
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    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
    • C11D3/0005—Other compounding ingredients characterised by their effect
    • C11D3/0026—Low foaming or foam regulating compositions
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
    • C11D3/16—Organic compounds

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  • An anionic (ktergent compositicm having an inverse 252/99 252/102 252/110 252/117 foam to temperature relationship is disclosed, as well 252/121 252/321, 252/358 252/527 as a composition for accomplishing this relationship 252/546, 252/547, 252/DIG- when added to a detergent system.
  • the inverse foam 252/DIG- to temperature relationship is provided by a syner- 1 'l Cl 1/12, Cl 1d 13/303301!
  • Foaming, or sudsing, of detergents is an extremely important factor to consider when formulating a detergent composition. It is known, for example, that a detergent which over-foams does not do an efficient job of cleaning in a washing machine. On the other hand, in hand washing there is a desire on the part of most consumers for a substantial amount of foam produced by a detergent. It is therefore necessary to provide a detergent composition which produces enough foam to reassure the consumer but yet not so much foam as to inhibit the detergent action of the composition. This need has been satisfactorily achieved in many ways.
  • washing machines are designed with internal water heating systems which begin their cycle with cold water and gradually heat the same to the desired operating temperature which is usually the boil." Such washing machines are used extensively, for instance, in many European countries. It is well known, however, that a detergent system which provides an adequate level of foam when used with hot water will not foam at all in cold water. Conversely, a detergent system which is compounded so that a sufficient level of foam is produced in cold water will overfoam to the extent of overflowing the washing machine when used with hot water.
  • a composition for regulating the foam profile of a detergent system, comprising a synergistic mixture, of a fatty acid and a polyethoxylated quaternary ammonium salt.
  • a detergent composition having an inverse foam-totemperature relationship which comprises an anionic detergent, inorganic builders, and a synergistic mixture of a fatty acid and a polyethoxylated quaternary ammonium salt.
  • the detergent composition could have other additives such as brighteners, germicides, soil suspending agents, antioxidants, bleaches, coloring materials, and perfume. It is quite unexpected to find that the mixture of fatty acids and polyethoxylated quaternary ammonium salts provide the inverse foamto-temperature relationship, since each of the ingredients, when used alone, does not exhibit any such properties.
  • the useful fatty acids which may be employed in the present invention include those saturated linear acids containing between about 8 and 30 carbon atoms in their alkyl chain. These include:
  • the preferred fatty acids are those having alkyl chains of from about 14 to 22 carbon atoms.
  • One such preferred fatty acid is stearic acid.
  • Another preferred acid composition is available commercially under the name Hyfac 431.
  • l-Iyfac 431 is a hydrogenated fish fatty acid having the following approximate composition:
  • Hystrene' 7022 comprises about C to C fatty acids.
  • Hystrene 9022 comprises about C to C fatty acids, and I-Iystrene 9018 has about 90 percent stearic acid.
  • Neofat 18-58 is a hydrogenated tallow acid.
  • the fatty acid, used in combination with the polyethoxylated quaternary ammonium salt, should be present in the final detergent composition in an amount from about 1 to about 6 percent by weight of the total detergent composition.
  • the polyethoxylated quaternary ammonium salt component of the synergistic mixture can be any such salt, although a polyethoxylated mono fatty alkyl methyl ammonium salt is preferred.
  • a polyethoxylated (40 moles of ethylene oxide) dicoco methyl ammonium methyl sulfate has been used.
  • the polyethoxylated (15 moles of EO) mono fatty alkyl methyl ammonium chlorides which are commercially available under the name Ethoquad.
  • the most preferred such salt is Ethoquad 18/25, which is polyethoxylated (15 moles) stearyl methyl ammonium chloride.
  • Other suitable quaternary salts having about to 50 moles ethylene oxide may be used. Any suitable anion can be used including other halides (e.g. bromide), nitrates and sulfates.
  • the useful detergents which may be used in conjunction with the foam profile regulating composition of the present invention include anionic detergents such as alkylbenzene-sulfonic acid and its salts, and compounds of the formula alky1-phenyl-SO -M, wherein alkyl is an alkyl radical of a fatty acid and M is hydrogen or an alkali metal, which compounds comprise a well known class of anionic detergents and include sodium dodecyl-benzene sulfonate, potassium dodecylbenzenesulfonate, sodium laurylbenzenesulfonate, sodium cetylbenzenesulfonate. Others are the alkali metal dialkyl sulfosuccinates, e.
  • the preferred compounds include those which are biodegradable and which are particularly characterized by a linear alkyl substituent of from C to C and preferably from C to C
  • the carbon chain length represents, in general, an average chain length since the method for producing such products usually employs alkylating reagents of mixed chain length.
  • substantially pure olefins as well as alkylating compounds used in other techniques can and do give alkylated benzene sulfonates wherein the alkyl moiety is substantially (i. e., at least 99 percent) of one chain length, i.
  • linear alkyl benzene sulfonates are further characterized by the position of the benzene ring in the linear alkyl chain, with any of the position isomers (i. e., alpha to omega) being operable and contemplated.
  • the linear alkyl benzene sulfonates are generally and conveniently prepared by sulfonating the corresponding alkyl benzene hydrocarbons which in turn may be prepared by alkylating benzene with a linear alkyl halide, a l-alkene or a linear primary or secondary alcohol.
  • Pure isomers (of the l-phenyl isomer) are prepared by reduction of the acylated benzene (alkyl phenyl ketone) using a modification of the Wolff- Keshner reaction.
  • the Z-phenyl isomer is obtained from n-undecyl phenyl ketone and methyl magnesium bromide to form the tertiary alcohol which is dehydrated to the alkene and then hydrogenated.
  • the S-phenyl isomer is obtained similarly from a n-heptyl phenyl ketone and n-butyl magnesium bromide.
  • benzene sulfonates may also employ the lower alkyl (C to C analogs of benzene such as toluene, xylene, the trimethyl benzenes, ethyl benzene, isopropyl benzene and the like.
  • the sulfonates are generally employed in the water soluble salt form which include as the cation, the alkali metals, ammonium, and lower amine and alkanolamine.
  • sulfonates may, of course, also be used with mixtures which may include compounds wherein the linear alkyl chain is smaller or larger than indicated herein provided that the average chain length in the mixture conforms to the specific requirements ofC to C
  • anionic detergents are the olefin sulfonates,including long chain alkene sulfonates, long chain hydroxyalkane sulfonates or mixtures of alkenesulfonates and hydroxyalkane-sulfonates.
  • linear paraffin sulfonates are also a well known group of compounds and include water soluble salts (alkali metal, amine, alkanolamine, and ammonium) of:
  • linear alkyl sulfates which are contemplated in this invention comprise the range ofC to C Specific examples include sodium n-decyl sulfate; sodium ndodecyl sulfate; sodium n-octadecyl sulfate; and the ethoxylated (l to moles ethylene oxide) derivatives; and of course, the other water soluble salt-forming cations mentioned above.
  • composition of the present invention may also include in addition to the foam profile regulating com pounds and conventional anionic detergent compositions builders, brighteners, hydrotropes, germicides, soil suspending agents, anti-redeposition agents, antioxidants, bleaches, coloring materials (dyes and pigments), perfumes, water soluble alcohols, non-detergent alkali metal benzene sulfonates, fabric softening compounds, enzymes, etc.
  • the builder is, generally, a water soluble, inorganic salt which may be a neutral salt, e. g., sodium sulfate or an alkaline builder salt such as phosphates, silicates, bicarbonates, carbonates, and borates.
  • the preferred builders are those characterized as condensed phosphates such as polyphosphates and pyrophosphates.
  • alkaline salts are: tetrasodium pyrophosphates, pentasodium tripolyphosphate (either Phase I or Phase 11), sodium hexametaphosphate, and the corresponding potassium salts of these compounds, sodium and potassium silicates, e.
  • sodium metasilicate and alkaline silicates Na O; 2Si0 and Na O; 3SiO sodium carbonate, potassium carbonate and sodium and potassium bicarbonate.
  • Other salts may also be used where the compounds are water soluble. These include the general class of alkali metal, alkaline earth metal, amine, alkanolamine, and ammonium salts.
  • Other builders which are salts of organic acids may also be used, and in particular the water soluble (alkali metal, ammonium, substituted ammonium and amine) salts of aminopolycarboxylic acids such as:
  • hydrotropes include such compounds as sodium xylene sulfonate, potassium xylene sulfonate, sodium and potassium toluene sulfonates, in the position isomers thereof, and ethyl benzene sulfonate.
  • composition for regulating the foam profile of a detergent there is employed from about to 75 percent fatty acid and from about 85 to 25 percent polyethoxylated quaternary ammonium salt. Preferably, there is employed from about 25 to 60 percent fatty acid and from about 75 to 40 percent polyethoxylated quaternary ammonium salt.
  • total detergent system there is employed from about 1 to 6 percent fatty acid and from about 1 to 6 percent polyethoxylated quaternary ammonium salt, and preferably from about 3 to 5 percent fatty acid and from about 2 to 3 percent polyethoxylated quaternary ammonium salt. All of said percentages are by weight, based on the total amount of the composition being used. In the case of the detergent systems, the percentages are based on an anionic detergent concentration of about 8 to 18 percent by weight. When less anionic detergent is present in the system, a
  • each of the fatty acid and the polyethoxylated quaternary ammonium salt can be used.
  • Builders when used may range from 10-85 wt percent.
  • EXAMPLE 1 In this example, several detergent systems were tested to determine their foam profile by means of a graduated cylinder shake test. The shake test is performed by adding 200 mililiters of the detergent solution to be tested to a 500 mililiter graduated cylinder. The cylinder is then shaken an established number of times, and the foam height and rate of suds collapse is noted. In each case, the detergent composition was 0.5 percent in tap water at 160 F. and the detergent formulations were as follows:
  • Formulation Ingredients l 2 3 Sodium tridecyl benzene sulfonate l0 l5 5 *Non-ionic detergent 2 5 Soap 2 2 Sodium tripolyphosphate 35 35 24 Trisodiurn nitriloacetate 5 Sodium carboxymethylcellulose 0.5 0.5 0.5 0.5 Polyvinyl alcohol 0.2 0.2 0.2 Sodium silicate 7.5 7.5 7.5 "Sodium sulfate Q5. 0.5. 0.8.
  • Formulation number 2 with both 4 percent Hyfac 431 and 4 percent Ethoquad 2C/50 DMS produced a foam which broke in about two minutes.
  • the detergent system with both Hyfac 431 and the polyethoxylated quaternary ammonium salt showed the desired foam profile.
  • EXAMPLE 3 Formulation number 2 was again tested, using the shake test, under the same conditions as in the previous examples, and with other additives.
  • Ethoquad 18/25 was substituted for Ethoquad 2C/50 DMS.
  • Ethoquad 18/25 is polyethoxylated moles) stearyl methyl ammonium chloride.
  • Other fatty acids which were tested were palmitic acid and triple pressed stearic acid.
  • Ethoquad 18/25 was used in concentrations up to 6 percent by weight. There was no change in the foam profile when only the polyethoxylated quaternary ammonium salt was used.
  • Palmitic acid, triple pressed stearic acid, and Hyfac 431 were evaluated in concentrations varying between 1.0 and 6 percent by weight.
  • FIG. 1 indicates the foam profile of the system with various concentrations of palmitic acid.
  • FIG. 2 illustrates the results obtained with stearic acid, and
  • FIG. 3 indicates the results obtained with Hyfac 431.
  • FIG. 4 illustrates the results obtained by adding Ethoquad 18/25 alone to the detergent composition, and compares that result with the addition of variable amounts of Hyfac 43 1, together with Ethoquad l8/25.
  • EXAMPLE 4 It should be noted that the previous examples used a detergent system comprising 15 percent linear alkyl benzene sulfonate* detergent. In this example, a system comprising 10 percent linear alkyl benzene sulfonate* detergent was evaluated. Three systems were formulated containing Ethoquad 18/25 and stearic acid, Ethoquad 18/25 and Hyfac 431, and Hyfac 431 alone, these formulations being denoted 4, 5 and 6 respectively. Their composition is as follows:
  • Example 6 The products of Example were re-evaluated with the addition of sodium perborate equivalent to 30 percent. The use of the sodium perborate did not effect the results. Additionally, formulations containing 30 percent sodium perborate and 1 percent magnesium sulfate and 0.25 percent EDTA to preserve and stabilize the sodium perborate were tested. Again, there was no change in the results.
  • the following examples demonstrate the foam profiles of various detergent systems under the conditions of use to be encountered in Europe.
  • the detergent compositions were tested in a Miele automatic washing machine, which is of German manufacture.
  • the machine is a front loading, tumbler type washing machine equipped with a heater that raises the water temperature from room temperature to the boil.
  • the machine operates on 220 volts, 50 cycle alternating current. In each instance, the machine was set on the white clothes setting, and a 5 pound load of clean clothing was used.
  • the water capacity is 1 1 liters.
  • a detergent concentration of 0.5 percent was used in each cycle. This detergent concentration was provided by using 56 grams of detergent.
  • the machine operates on two cycles, a pre-wash cycle and a wash cycle.
  • a pre-wash cycle the temperature of the water climbs from 70 to 120 F, and the total cycle is 12 to 14 minutes.
  • the drum rotates for about seconds, rests for 4 seconds, reverses direction, and the operation is repeated.
  • the machine stops, drains, and remains motionless until the wash cycle starts.
  • the wash cycle is divided into two stages, the heating stage and the washing stage.
  • the heating stage cold water washes a second charge of detergent into the drum.
  • the temperature climbs from about 90 F to over 190 F.
  • the drum rotates for 4 to 5 seconds, rests for 10 seconds, reverses direction, and repeats the operation.
  • the machine changes its drum action and goes into the washing stage.
  • the washing stage lasts 18 minutes. During this time, the drum action is the same as that described for the pre-wash cycle.
  • the temperature fluctuates between 190 and 200 F during the whole washing stage.
  • fatty acids or the like includes the corresponding water-soluble soaps thereof, preferably the alkali metal soaps such as sodium and potassium.
  • the fatty acids per se and soaps thereof may be used interchangeably depending upon economics, method of manufacture of the composition with other ingredients and its use in washing.
  • fatty acids may exist in the product when post-added to a detergent powder; or partly or wholly in the form of soap when added to a slurry or solution during manufacture of detergent products in the presence of alkaline materials or in alkaline washing solutions.
  • a composition for regulating the foam profile of a detergent system consisting essentially of (1) from about 15 to 75 percent of fatty acid containing between about eight and 30 carbon atoms in the alkyl chain, and (2) from about to 25 percent of polyethoxylated, mono fatty alkyl quaternary ammonium methosulfate, chloride, bromide, nitrate or sulfate salt having about 10 to 50 moles of ethylene oxide.
  • composition according to claim 1 wherein said fatty acid contains from about 14 to 22 carbon atoms.
  • composition according to claim 2 wherein said fatty acid is stearic acid.
  • composition according to claim 2 wherein said fatty acid is hydrogenated fish fatty acid.
  • composition according to claim 2 wherein said fatty acid is hydrogenated tallow acid.
  • composition according to claim 2 wherein said fatty acid is a mixture of C to C fatty acids.
  • composition according to claim 1 wherein said fattyacid is present in from about 25 to 60 percent by weight of said composition.
  • composition according to claim 1 wherein said salt is a polyethoxylated (15 mole) mono fatty alkyl methyl ammonium chloride.
  • composition according to claim 8 wherein said salt is polyethoxylated (15 mole) stearyl methyl ammonium chloride.
  • composition according to claim 1 wherein said salt is polyethoxylated (40 mole) dicoco methyl ammonium sulfate.
  • composition according to claim 1 wherein said salt is present in from about 75 to 40 percent by weight of said composition.
  • a detergent composition having an inverse foam to temperature relationship consisting essentially of (1) from about 1 to 6 percent by weight of fatty acid containing between about eight and 30 carbon atoms in the alkyl chain, (2) from about 1 to 6 percent by weight of polyethoxylated mono fatty alkyl quaternary ammonium methosulfate, chloride, bromide, nitrate or sulfate salt having about to 50 moles of ethylene oxide, and (3) from about 8 to 18 percent by weight of anionic detergent.
  • a composition according to claim 12, wherein said anionic detergent is a linear alkyl benzene sulfonate having about 10 to 22 carbon atoms in the alkyl group.
  • composition according to claim 13 wherein said alkyl group has about 12 to 15 carbon atoms.
  • a composition according to claim 12 which includes about 10 to 15 percent linear alkyl benzene sulfonate, and builder salts selected from the group consisting of alkali metal and ammonium polyphosphates, silicates, borates, sulfates and combinations thereof.
  • composition according to claim 12 wherein said fatty acid contains from about 14 to 22 carbon atoms.
  • composition according to claim 16 wherein said fatty acid is stearic acid.
  • composition according to claim 16 wherein said fatty acid is hydrogenated fish fatty acid.
  • composition according to claim 16 wherein said fatty acid is hydrogenated tallow acid.
  • composition according to claim 16 wherein said fatty acid is a mixture of C to C fatty acids.
  • composition according to claim 12 wherein said fatty acid is present in from about 3 to 5 percent by weight of said composition.
  • composition according to claim 12 wherein said salt is a polyethoxylated (15 mole) mono fatty alkyl methyl ammonium chloride.
  • composition according to claim 22, wherein said salt is polyethoxylated (15 mole) stearyl methyl ammonium chloride.
  • composition according to claim 12 wherein said salt is polyethoxylated (40 mole) dicoco methyl ammonium sulfate.

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US00041359A 1970-05-28 1970-05-28 Foam profile regulating composition and anionic detergent composition containing same and having inverse foam to temperature relationship Expired - Lifetime US3714074A (en)

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US4139270A 1970-05-28 1970-05-28
US4135870A 1970-05-28 1970-05-28
US4130870A 1970-05-28 1970-05-28
US4135970A 1970-05-28 1970-05-28
US4160270A 1970-05-28 1970-05-28
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US00041359A Expired - Lifetime US3714074A (en) 1970-05-28 1970-05-28 Foam profile regulating composition and anionic detergent composition containing same and having inverse foam to temperature relationship
US41308A Expired - Lifetime US3704267A (en) 1970-05-28 1970-05-28 Ternary foam control composition and built anionic detergent composition containing same
US41392A Expired - Lifetime US3696056A (en) 1970-05-28 1970-05-28 Ternary foam control systems with amines or amides and detergent compositions containing same
US00041358A Expired - Lifetime US3730912A (en) 1970-05-28 1970-05-28 Ternary foam control systems and detergent compositions containing same
US00041601A Expired - Lifetime US3716499A (en) 1970-05-28 1970-05-28 Ternary foam control composition and built anionic detergent composition containing same
US00041602A Expired - Lifetime US3709836A (en) 1970-05-28 1970-05-28 Built anionic detergent composition having inverse foam-to-temperature relationship and process for producing same

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US41392A Expired - Lifetime US3696056A (en) 1970-05-28 1970-05-28 Ternary foam control systems with amines or amides and detergent compositions containing same
US00041358A Expired - Lifetime US3730912A (en) 1970-05-28 1970-05-28 Ternary foam control systems and detergent compositions containing same
US00041601A Expired - Lifetime US3716499A (en) 1970-05-28 1970-05-28 Ternary foam control composition and built anionic detergent composition containing same
US00041602A Expired - Lifetime US3709836A (en) 1970-05-28 1970-05-28 Built anionic detergent composition having inverse foam-to-temperature relationship and process for producing same

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US4686060A (en) * 1986-01-23 1987-08-11 The Procter & Gamble Company Detergent composition providing rinse cycle suds control containing a soap, a quaternary ammonium salt and a silicone
US4847089A (en) * 1986-07-16 1989-07-11 David N. Kramer Cleansing and distinfecting compositions, including bleaching agents, and sponges and other applicators incorporating the same
US4915854A (en) * 1986-11-14 1990-04-10 The Procter & Gamble Company Ion-pair complex conditioning agent and compositions containing same
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US5019280A (en) * 1986-11-14 1991-05-28 The Procter & Gamble Company Ion-pair complex conditioning agent with benzene sulfonate/alkyl benzene sulfonate anionic component and compositions containing same
US4756850A (en) * 1987-06-10 1988-07-12 The Procter & Gamble Company Articles and methods for treating fabrics
US4913828A (en) * 1987-06-10 1990-04-03 The Procter & Gamble Company Conditioning agents and compositions containing same
US5073274A (en) * 1988-02-08 1991-12-17 The Procter & Gamble Co. Liquid detergent containing conditioning agent and high levels of alkyl sulfate/alkyl ethoxylated sulfate
US4857213A (en) * 1988-02-08 1989-08-15 The Procter & Gamble Company Liquid detergent containing conditioning agent and high levels of alkyl sulfate/alkyl ethoxylated sulfate
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Cited By (12)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3910855A (en) * 1972-05-16 1975-10-07 Richard M Abeles Liquid cleaning compositions
US3959165A (en) * 1972-09-15 1976-05-25 Colgate-Palmolive Company Biodegradable, non-polluting, heavy duty synthetic organic detergent composition
US4028262A (en) * 1972-10-16 1977-06-07 Colgate-Palmolive Company Citrate-carbonate built detergent
US3920563A (en) * 1972-10-31 1975-11-18 Colgate Palmolive Co Soap-cationic combinations as rinse cycle softeners
US4167561A (en) * 1973-12-28 1979-09-11 Lever Brothers Company Hypochlorite disinfecting compositions and use thereof
US4153570A (en) * 1977-02-01 1979-05-08 Henkel Kommanditgesellschaft Auf Aktien (Henkel Kgaa) Low-foaming liquid washing agent concentrates
US4308024A (en) * 1978-11-03 1981-12-29 Lever Brothers Company Fabric softening composition
USRE34062E (en) * 1978-11-03 1992-09-15 Lever Brothers Company Fabric softening composition contains water-insoluble surfactant and aliphatic mono-carboxylic acid
US4284435A (en) * 1979-11-28 1981-08-18 S. C. Johnson & Son, Inc. Method for spray cleaning painted surfaces
US4492646A (en) * 1980-02-05 1985-01-08 The Procter & Gamble Company Liquid dishwashing detergent containing anionic surfactant, suds stabilizer and highly ethoxylated nonionic drainage promotor
US4561998A (en) * 1982-05-24 1985-12-31 The Procter & Gamble Company Near-neutral pH detergents containing anionic surfactant, cosurfactant and fatty acid
US4637890A (en) * 1986-01-23 1987-01-20 The Procter & Gamble Company Detergent composition providing rinse cycle suds and turbidity control containing a soap, quaternary ammonium salt and a silicone

Also Published As

Publication number Publication date
NL7107442A (enExample) 1971-11-30
GB1286054A (en) 1972-08-16
US3696056A (en) 1972-10-03
CA949417A (en) 1974-06-18
US3709836A (en) 1973-01-09
US3730912A (en) 1973-05-01
DK138662C (enExample) 1979-03-19
CA945036A (en) 1974-04-09
BE767873A (fr) 1971-10-18
CA954004A (en) 1974-09-03
DE2126061A1 (de) 1971-12-09
CA944652A (en) 1974-04-02
US3704267A (en) 1972-11-28
CA945034A (en) 1974-04-09
US3716499A (en) 1973-02-13
SE382464B (sv) 1976-02-02
CH552053A (de) 1974-07-31
CA945037A (en) 1974-04-09
DK138662B (da) 1978-10-09
FR2093742A5 (enExample) 1972-01-28
AT325182B (de) 1975-10-10

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