US3470102A - Detergent composition - Google Patents
Detergent composition Download PDFInfo
- Publication number
- US3470102A US3470102A US521550A US3470102DA US3470102A US 3470102 A US3470102 A US 3470102A US 521550 A US521550 A US 521550A US 3470102D A US3470102D A US 3470102DA US 3470102 A US3470102 A US 3470102A
- Authority
- US
- United States
- Prior art keywords
- foam
- foaming
- ammonyx
- oxide
- cea
- 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 - Lifetime
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Classifications
-
- 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
- C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
- C11D1/66—Non-ionic compounds
- C11D1/75—Amino oxides
-
- 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
Definitions
- This invention relates to low foaming detergent compositions having controlled sudsing capacity.
- foam stabilising agents in detergent compositions to impr prove the persistence and the stability of the foam produced by agitation of the wash liquors.
- the prior art compound which function as foam stabilising agents in detergent systems depend upon Well-known foam-stabilising functional groups such as the amide, alcolohic, and phenolic hydroxyl groups.
- foam stabilising agents are fatty alcohols, fatty acid monoalkanolamides, fatty acid dialkanolamides, p-hydroxylaurophenone and alkylene oxide adducts with a short polyglycol chain such as nonylphenol/4 E.O.
- foam stabilising agent do not produce any significant amount of foam themselves, but influence the system in such a way that it becomes less sensitive to soil, so that the foam-depressing action of soil in a wash liquor is decreased.
- R is a branched or straight-chain alkyl radical, containing from to 18 carbon atoms, and R and R are each alkyl radicals containing from 1 to 3 carbon atoms.
- these amine oxides are lauryl-, myristyl-, stearyl-dimethylamine oxides. Also mixtures of any of the foregoing compounds may be used according to the present invention.
- Suitable foam stabilising agents according to the present invention are those mentioned priviously. Especially suitable are the fatty acid alkanolamides, such as coconut fatty acid monoand di-ethanolamides, tallow fatty acid mono-ethanolamide, etc. Also mixtures of any of these foam-stabilisers may be used.
- the Weight ratio of amine oxides to foam stabilising agent is from 25:1 to 1:2. The amine oxides are not included in the term foam-stabilising agent.
- the detergent compositions according to the present invention show their controlled sudsing characteristics over a wide temperature range, viz. from 20 to C., while the water hardness does not influence the foam stability; the foam produced is of a fine texture. They also have excellent detergency characteristics, and are mild in their action towards the skin.
- the composition may include other constituents, provided its low-sudsing character is not impaired and may naturally contain all the usual constitutents desirable in a built detergent composition, such as phosphates, silicates, bleaching agents, Whitening agent, perfumes, soil-suspending agents, etc. They may be prepared in any desired physical form, such as powders, pastes, liquids and solids and are suitable for use a dish washing composition, light and heavy duty detergent compositions, hard-surface cleaners and scouring powders.
- the foaming height was compared with the foaming heights of the solutions obtained by adding to the above solution 0.15 g./l., 0.25 g./l. and 0.5 g./l. of coconut monoethanolamide (CEA).
- the foaming heights of a 1 litre aqueous solution of a mixture of 1 g. of a commercial tridecyldimethylamine oxide, known under the trade name Noxamine C50 (equivalent to 0.52 g. tridecyldimethyl amine oxide as dry substance) and 2 g. sodium tripolyphosphate with and without 0.15 g. coconut monoethanolamide were determined in water of DH and 15 DH. The following results were obtained:
- EXAMPLE 3 Three aqueous solutions were prepared each containing 2 g./l. sodium tripolyphosphate (STPP) and 1 g./l. of a different commercial amine oxide, viz. 1aury1, myristyland cetyldimethylamine oxide, as supplied under the trade names Ammonyx LO, MO and CO respectively. The foaming height of each of these combinations was determined with 0 and 1 g. soil per litre. These values were compared with those obtained with the same systems to which 0.15 g. coconut monoethanolamide was adde. The following results were obtained:
- Example 3 was repeated using different foam stabilisers, viz. lauric monoethanolamide '(LEA), tallow monoethanolamide (TEA) and coconut diethanolamide 4 (CDEA). The following results were obtained in the absence of soil:
- Ammonyx L0 LEA g./l. TEA, g./l. CDEA, g./l.
- Ammonyx MO LEA g./l. TEA, g.ll. CDEA, g./l.
- Ammonyx C0 LEA g./l. TEA, g./l. CDEA, g./l.
- EXAMPLE 5 The foaming height of an aqueous solution containing 2.83 g./1. Ammonyx CO and 2 g./l. STPP was compared with that of the same solution to which 0.15 g./l. nonylphenol condensed with 4 moles ethylene oxide was added. The following results were obtained:
- EXAMPLE 6 In a Wyandotte dynamic foam meter (as described in Soap and Chemical Specialties, April 1961, pages 55-57, 104) the foam capacity of aqueous solutions containing 2.83 g./l. of Ammonyx CO equivalent to 1 g./l. of cetyl dimethyl amine oxide as dry substance or 3.21 g./l. of Ammonyx SO (equivalent to 1 g./l. stearyl dimethyl amine oxide as dry substance) and 2 g./l. STPP with and without 0.25 g./l. CEA was determined. 200 ml./ min. of solution was used (water hardness 15 DH). The warming-up time was 34 minutes. The following results were obtained:
- EXAMPLE 7 The foaming height of an aqueous solution containing 3.33 g./1. of a commercial branched tridecyldimethyl amine oxide (supplied under the code name CWA 40-29 ex Union Carbide Cy.) equivalent to 1 g./1. of tridecyldimethyl amine oxide as dry substance and 2 g./l. of STPP was compared with that of the same solution to which 0.25 g./l. of CEA was added.
- a commercial branched tridecyldimethyl amine oxide supplied under the code name CWA 40-29 ex Union Carbide Cy.
- EXAMPLE 8 The foaming height of an aqueous solution containing per litre a mixture of 1.57 g. of Ammonyx MO (equivalent to 0.5 g. myristyldimethyl amine oxide as a dry substance) and 1.6 g. of Ammonyx SO (equivalent to 0.5 g. stearyldimethyl amine oxide as dry substance) and 2 g. of STPP was compared with the foaming height of the same solution to which 0.25 or 0.5 g./l. of a mixture of coconut monoethanolamide and tallow monoethanolamide (ratio of 1:1) were added.
- CEA plus TEA g./1.
- EXAMPLE 9 The foaming height of an aqueous solution containing per litre 2.83 g. of Ammonyx CO, 2 g. of STPP and 0.25
- a low-foaming detergent composition having controlled sudsing capacity consisting essentially of an amine oxide, as the only active organic detergent component, of
Description
United States Patent Office 3,470,102 Patented Sept. 30, 1969 3,470,102 DETERGENT COMPOSITION Karl Ludwig Heinz, Vlaardingen, Netherlands, assignor to Lever Brothers Company, New York, N.Y., a corporation of Maine No Drawing. Filed Jan. 19, 1966, Ser. No. 521,550 Claims priority, application Great Britain, Jan. 22, 1965, 2,962/65 Int. Cl. Clld 1/40 US. Cl. 252152 1 Claim ABSTRACT OF THE DISCLOSURE A low-foaming detergent composition having controlled sudsing capacity which contains as essential components thereof a tertiary amine oxide and a foam-stabilizing agent.
This invention relates to low foaming detergent compositions having controlled sudsing capacity.
It has been acknowledged in the detergent art that in many cases a high production of foam is undesirable, e.g. when using a detergent composition in automatic washing machines. Various so-called low-foaming detergent compositions have been developed in which substances have been incorporated which exerted a foam-depressing action.
It has furthermore been common practice to include foam stabilising agents in detergent compositions to impr prove the persistence and the stability of the foam produced by agitation of the wash liquors. The prior art compound which function as foam stabilising agents in detergent systems depend upon Well-known foam-stabilising functional groups such as the amide, alcolohic, and phenolic hydroxyl groups. Examples of foam stabilising agents are fatty alcohols, fatty acid monoalkanolamides, fatty acid dialkanolamides, p-hydroxylaurophenone and alkylene oxide adducts with a short polyglycol chain such as nonylphenol/4 E.O. These foam stabilising agent do not produce any significant amount of foam themselves, but influence the system in such a way that it becomes less sensitive to soil, so that the foam-depressing action of soil in a wash liquor is decreased.
It has now been found that when using one or more of such foam stabilising agents together with one or more of certain amine oxides, a detergent composition is obtained which not only has a great foam stability, but also a low or at least reduced foaming capacity, i.e. controlled sudsing. This is the more surprising, since the amine oxides in question, examples of which will be given below, have a high foam production, and accordingly it would be expected that, by using such a substance together with a foam stabilising agent, a stabilised high foam level would be obtained. The compositions according to the present invention show, however, a foam level appreciably lower than that of the amine oxides alone.
The amine oxides to be used in the compositions of the invention are known in the prior art and are represented by the formula:
in which R is a branched or straight-chain alkyl radical, containing from to 18 carbon atoms, and R and R are each alkyl radicals containing from 1 to 3 carbon atoms. Examples of these amine oxides are lauryl-, myristyl-, stearyl-dimethylamine oxides. Also mixtures of any of the foregoing compounds may be used according to the present invention.
Suitable foam stabilising agents according to the present invention are those mentioned priviously. Especially suitable are the fatty acid alkanolamides, such as coconut fatty acid monoand di-ethanolamides, tallow fatty acid mono-ethanolamide, etc. Also mixtures of any of these foam-stabilisers may be used. The Weight ratio of amine oxides to foam stabilising agent is from 25:1 to 1:2. The amine oxides are not included in the term foam-stabilising agent.
The detergent compositions according to the present invention show their controlled sudsing characteristics over a wide temperature range, viz. from 20 to C., while the water hardness does not influence the foam stability; the foam produced is of a fine texture. They also have excellent detergency characteristics, and are mild in their action towards the skin. The composition may include other constituents, provided its low-sudsing character is not impaired and may naturally contain all the usual constitutents desirable in a built detergent composition, such as phosphates, silicates, bleaching agents, Whitening agent, perfumes, soil-suspending agents, etc. They may be prepared in any desired physical form, such as powders, pastes, liquids and solids and are suitable for use a dish washing composition, light and heavy duty detergent compositions, hard-surface cleaners and scouring powders.
The present invention is illustrated by the following examples:
EXAMPLE 1 The foaming height of an aqueous solution containing per litre:
2.83 g. of a commercial cetyldimethylamine oxide known under the trade name Ammonyx CO (equivalent to 1 g. cetyldimethylamine oxide as dry substance), and 2 g. sodium tripolyphosphate,
was determined in the presence of different amounts of soil by the Ross-Miles test at 45 C., the water hardness being 15 DH (i.e., German hardness). The foaming height was compared with the foaming heights of the solutions obtained by adding to the above solution 0.15 g./l., 0.25 g./l. and 0.5 g./l. of coconut monoethanolamide (CEA).
The results obtained are given in the following table:
Foaming heights in cm. CEA g./l.
To illustrate the insensitivity of the compositions of the invention to the water hardness, the foaming heights of a 1 litre aqueous solution of a mixture of 1 g. of a commercial tridecyldimethylamine oxide, known under the trade name Noxamine C50 (equivalent to 0.52 g. tridecyldimethyl amine oxide as dry substance) and 2 g. sodium tripolyphosphate with and without 0.15 g. coconut monoethanolamide were determined in water of DH and 15 DH. The following results were obtained:
Foaming heights in em. in
water of 0 DH CEA added in g./l.
Foaming heights in em. in water of 15 DH CEA added in g./l.
Soil, g./1.:
This example clearly shows the insensitivity of the composition according to the present invention to the water hardness with regard to the stability and the reduced level of the foam.
EXAMPLE 3 Three aqueous solutions were prepared each containing 2 g./l. sodium tripolyphosphate (STPP) and 1 g./l. of a different commercial amine oxide, viz. 1aury1, myristyland cetyldimethylamine oxide, as supplied under the trade names Ammonyx LO, MO and CO respectively. The foaming height of each of these combinations was determined with 0 and 1 g. soil per litre. These values were compared with those obtained with the same systems to which 0.15 g. coconut monoethanolamide was adde. The following results were obtained:
Foaming height of a solution containing 1 g./l. Ammonyx LO (equivalent to 0.34 g./l. lauryldimethylamine oxide as dry snbstanee)+2 g./l. STP1 CEA in g./1.
Soil, g./1
l g./l. Ammonyx MO (equivalent to 0.32 g./l. myristyldimethylemine oxide as dry substance)+2 g./l. STPP+ CEA in g./l.
sonbgfld 15 o 4 5 11:11:11: 510 5:5
1 g./l. Ammonyx CO (equivalent to 0.35 g./l. cetyldimethylamine oxide as dry substance) +2 g./l. STPP+ CEA in g./l.
These results clearly show a reduced foam level and a great foam stability in respect of the composition of the invention.
EXAMPLE 4 Example 3 was repeated using different foam stabilisers, viz. lauric monoethanolamide '(LEA), tallow monoethanolamide (TEA) and coconut diethanolamide 4 (CDEA). The following results were obtained in the absence of soil:
Ammonyx L0 LEA, g./l. TEA, g./l. CDEA, g./l.
0 0.15 0 0. 15 0 0. 15 Foam height in cm..." 15.0 7.0 15.0 12.0 15. 0 6. 5
Ammonyx MO LEA, g./l. TEA, g.ll. CDEA, g./l.
0 0. 15 O 0. 15 0 0. 15 Foam height in cm..." 15.0 4. 5 15.0 8.5 15. 0 5. 5
Ammonyx C0 LEA, g./l. TEA, g./l. CDEA, g./l.
0 0. 15 0 0. 15 0 0. 15 Foam height in cm 8.5 2. 5 8. 5 3 2. 5
These results clearly show the reduction of foam by the addition of different foam stabilisers.
EXAMPLE 5 The foaming height of an aqueous solution containing 2.83 g./1. Ammonyx CO and 2 g./l. STPP was compared with that of the same solution to which 0.15 g./l. nonylphenol condensed with 4 moles ethylene oxide was added. The following results were obtained:
N ony1phenol/4 E.O. g./l.
This example illustrates that the foam stability and foam reduction are maintained by the addition of nonylphenol/4 E.O.
EXAMPLE 6 In a Wyandotte dynamic foam meter (as described in Soap and Chemical Specialties, April 1961, pages 55-57, 104) the foam capacity of aqueous solutions containing 2.83 g./l. of Ammonyx CO equivalent to 1 g./l. of cetyl dimethyl amine oxide as dry substance or 3.21 g./l. of Ammonyx SO (equivalent to 1 g./l. stearyl dimethyl amine oxide as dry substance) and 2 g./l. STPP with and without 0.25 g./l. CEA was determined. 200 ml./ min. of solution was used (water hardness 15 DH). The warming-up time was 34 minutes. The following results were obtained:
Foam height in mm.
These results illustrate the foam stability and reduced foam over a wide temperature range of the compositions of the invention.
EXAMPLE 7 The foaming height of an aqueous solution containing 3.33 g./1. of a commercial branched tridecyldimethyl amine oxide (supplied under the code name CWA 40-29 ex Union Carbide Cy.) equivalent to 1 g./1. of tridecyldimethyl amine oxide as dry substance and 2 g./l. of STPP was compared with that of the same solution to which 0.25 g./l. of CEA was added.
EXAMPLE 8 The foaming height of an aqueous solution containing per litre a mixture of 1.57 g. of Ammonyx MO (equivalent to 0.5 g. myristyldimethyl amine oxide as a dry substance) and 1.6 g. of Ammonyx SO (equivalent to 0.5 g. stearyldimethyl amine oxide as dry substance) and 2 g. of STPP was compared with the foaming height of the same solution to which 0.25 or 0.5 g./l. of a mixture of coconut monoethanolamide and tallow monoethanolamide (ratio of 1:1) were added.
CEA plus TEA, g./1.
EXAMPLE 9 The foaming height of an aqueous solution containing per litre 2.83 g. of Ammonyx CO, 2 g. of STPP and 0.25
g. of cetyl alcohol was compared with that of the same solution from which the cetyl alcohol was left out.
Cetyl alcohol Soi1,g.1
What is claimed is:
1. A low-foaming detergent composition having controlled sudsing capacity consisting essentially of an amine oxide, as the only active organic detergent component, of
3 the formula:
2,773,834 12/1956 Henkin 252152 3,086,943 4/1963 Lang 252-152 3,223,647 12/1965 Drew et al. 252-152 3,281,368 10/1966 Zimmerer et a1. 252152 3,317,430 5/1967 Priestley et al. 252-152 LEON D. ROSDOL, Primary Examiner S. D. SCHWARTZ, Assistant Examiner US. Cl. X.R. 252-l37; 424
UNITED STATES PATENT OFFICE CERTIFICATE OF CORRECTIQN Patent No. 3, 7 102 Dated September 30, 1969 Inventor(s) It is certified that error appears in the above-identified patent and that said Letters Patent are hereby corrected as shown below:
Column 1, line 30, "impr" should be imline 32, "compound" should be --compounds- Column 2, line 2, "priviously" should be --previously--; line 7, "oxides" should be --oxide--; line 19, constitutencs should be -constituents-; line 21, "agent first occurrence, should be --agents-- "a dish washing compositioi line 2 should read --as dish washing compositions--. Column 3,
H II 5-5 line 42, "adde" should be --added--; line 58, should be --4.5-- line 69 "composition" should be --compositions-. Column 1, line 16, ".85" should be -8.5--. Column 6, line 22, "carbons" should be -carbon- SIGNED AND SEALED MAY 1 21978 T6 (S Atteat:
WILLIAM E. 'SCERWLER, JR. Commissioner of Patents Edward M. Fletcher, Ir. Attesting Officer
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GB2962/65A GB1131492A (en) | 1965-01-22 | 1965-01-22 | Detergent composition |
Publications (1)
Publication Number | Publication Date |
---|---|
US3470102A true US3470102A (en) | 1969-09-30 |
Family
ID=9749312
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US521550A Expired - Lifetime US3470102A (en) | 1965-01-22 | 1966-01-19 | Detergent composition |
Country Status (11)
Country | Link |
---|---|
US (1) | US3470102A (en) |
AT (1) | AT284305B (en) |
BE (1) | BE675450A (en) |
CA (1) | CA786293A (en) |
CH (1) | CH475344A (en) |
DE (1) | DE1617206A1 (en) |
ES (1) | ES322080A1 (en) |
FR (1) | FR1465181A (en) |
GB (1) | GB1131492A (en) |
LU (1) | LU50303A1 (en) |
NL (2) | NL6600551A (en) |
Cited By (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3943234A (en) * | 1973-08-09 | 1976-03-09 | The Procter & Gamble Company | Acidic emollient liquid detergent composition |
US4048338A (en) * | 1973-11-09 | 1977-09-13 | Colgate-Palmolive Company | Aqueous cosmetic composition containing amine oxides |
US4065409A (en) * | 1975-08-01 | 1977-12-27 | Corporate Brands, Inc. | Hard surface detergent composition |
US4741863A (en) * | 1984-02-10 | 1988-05-03 | Toyota Jidosha Kabushiki Kaisha | Alkaline degreasing solution comprising amine oxides |
US4921627A (en) * | 1986-11-14 | 1990-05-01 | Ecolab Inc. | Detersive system and low foaming aqueous surfactant solutions containing a mono(C1-4 alkyl)-di(C6-20) alkylamine oxide compound |
Citations (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2773834A (en) * | 1953-09-21 | 1956-12-11 | Colgate Palmolive Co | Shampoo compositions containing monomethylol dimethyl hydantoin |
US3086943A (en) * | 1959-06-10 | 1963-04-23 | Procter & Gamble | Shampoo containing amine oxide |
US3223647A (en) * | 1959-04-20 | 1965-12-14 | Procter & Gamble | Mild detergent compositions |
US3281368A (en) * | 1961-12-04 | 1966-10-25 | Procter & Gamble | Built tertiary amine oxide detergents |
US3317430A (en) * | 1960-05-05 | 1967-05-02 | Lever Brothers Ltd | Detergent compositions |
-
0
- NL NL131045D patent/NL131045C/xx active
- CA CA786293A patent/CA786293A/en not_active Expired
-
1965
- 1965-01-22 GB GB2962/65A patent/GB1131492A/en not_active Expired
-
1966
- 1966-01-14 CH CH47466A patent/CH475344A/en not_active IP Right Cessation
- 1966-01-17 NL NL6600551A patent/NL6600551A/xx unknown
- 1966-01-19 US US521550A patent/US3470102A/en not_active Expired - Lifetime
- 1966-01-21 BE BE675450D patent/BE675450A/xx unknown
- 1966-01-21 ES ES0322080A patent/ES322080A1/en not_active Expired
- 1966-01-21 DE DE19661617206 patent/DE1617206A1/en active Pending
- 1966-01-21 FR FR46865A patent/FR1465181A/en not_active Expired
- 1966-01-21 AT AT55866A patent/AT284305B/en not_active IP Right Cessation
- 1966-01-21 LU LU50303A patent/LU50303A1/xx unknown
Patent Citations (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2773834A (en) * | 1953-09-21 | 1956-12-11 | Colgate Palmolive Co | Shampoo compositions containing monomethylol dimethyl hydantoin |
US3223647A (en) * | 1959-04-20 | 1965-12-14 | Procter & Gamble | Mild detergent compositions |
US3086943A (en) * | 1959-06-10 | 1963-04-23 | Procter & Gamble | Shampoo containing amine oxide |
US3317430A (en) * | 1960-05-05 | 1967-05-02 | Lever Brothers Ltd | Detergent compositions |
US3281368A (en) * | 1961-12-04 | 1966-10-25 | Procter & Gamble | Built tertiary amine oxide detergents |
Cited By (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3943234A (en) * | 1973-08-09 | 1976-03-09 | The Procter & Gamble Company | Acidic emollient liquid detergent composition |
US4048338A (en) * | 1973-11-09 | 1977-09-13 | Colgate-Palmolive Company | Aqueous cosmetic composition containing amine oxides |
US4065409A (en) * | 1975-08-01 | 1977-12-27 | Corporate Brands, Inc. | Hard surface detergent composition |
US4741863A (en) * | 1984-02-10 | 1988-05-03 | Toyota Jidosha Kabushiki Kaisha | Alkaline degreasing solution comprising amine oxides |
US4921627A (en) * | 1986-11-14 | 1990-05-01 | Ecolab Inc. | Detersive system and low foaming aqueous surfactant solutions containing a mono(C1-4 alkyl)-di(C6-20) alkylamine oxide compound |
Also Published As
Publication number | Publication date |
---|---|
FR1465181A (en) | 1967-01-06 |
GB1131492A (en) | 1968-10-23 |
BE675450A (en) | 1966-05-16 |
CH475344A (en) | 1969-07-15 |
LU50303A1 (en) | 1966-03-21 |
DE1617206A1 (en) | 1971-02-25 |
NL131045C (en) | |
AT284305B (en) | 1970-09-10 |
CA786293A (en) | 1968-05-28 |
ES322080A1 (en) | 1966-11-16 |
NL6600551A (en) | 1966-07-25 |
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