DE2437090A1 - CLEANING SUPPLIES - Google Patents
CLEANING SUPPLIESInfo
- Publication number
- DE2437090A1 DE2437090A1 DE2437090A DE2437090A DE2437090A1 DE 2437090 A1 DE2437090 A1 DE 2437090A1 DE 2437090 A DE2437090 A DE 2437090A DE 2437090 A DE2437090 A DE 2437090A DE 2437090 A1 DE2437090 A1 DE 2437090A1
- Authority
- DE
- Germany
- Prior art keywords
- sodium
- cleaning agent
- liquid
- weight
- solubilizers
- 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.)
- Pending
Links
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
- C11D1/88—Ampholytes; Electroneutral compounds
- C11D1/94—Mixtures with anionic, cationic or non-ionic compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic System
- C07F9/02—Phosphorus compounds
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/54—Quaternary phosphonium compounds
-
- 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
- C11D1/88—Ampholytes; Electroneutral compounds
-
- 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
- C11D1/88—Ampholytes; Electroneutral compounds
- C11D1/886—Ampholytes containing P
-
- 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
- C11D3/36—Organic compounds containing phosphorus
- C11D3/361—Phosphonates, phosphinates or phosphonites
Description
HOECHST AKTIENGESELLSCHAFT , . 243/090HOECHST AKTIENGESELLSCHAFT,. 243/090
Aktenzeichen: HOE 74/F 219
Datum: 29- Juli 197^ Dr. GR/stlFile number: HOE 74 / F 219
Date: July 29, 197 ^ Dr. GR / stl
Reinigungsmittelcleaning supplies
Die Erfindung betrifft pulverförmige oder flüssige wäßrige Reinigungsmittel-Konzentrate für die Verwendung in Haushalt und Industrie.The invention relates to powdery or liquid aqueous cleaning agent concentrates for household and industrial use.
Moderne Reinigungsmittel für die Reinigung von Oberflächen nicht textiler Materialien, die sowohl zur Reinigung von Hand als auch in modernen Reinigungsanlagen, wie z.B. Strahlreinigungsanlagen, , Heißwassergeräten, DampfStrahlgeräten und dergleichen, als flüssige oder pulverförmige Industrie- und Haushaltsreiniger, flüssige Geschirreiniger und flüssige Schwerwaschmittel eingesetzt, bestehen im wesentlichen aus. nichtionischen, anionischen und/oder amphoteren Tensiden, Gerüststoffen und Lösungsvermittlern.Modern detergents for cleaning surfaces do not textile materials that can be used for cleaning by hand as well as in modern cleaning systems, such as blast cleaning systems, Hot water devices, steam jet devices and the like, as liquid or powdered industrial and household cleaners, liquid dishwashing detergents and liquid heavy-duty detergents are used essentially from. nonionic, anionic and / or amphoteric surfactants, builders and solubilizers.
Die Mitverwendung von LösungsVermittlern ist erforderlich, wenn derartige Reinigungsmittel als konzentrierte flüssige Zubereitungen hergestellt werden. Ihre Mitverwendung ist auch bei solchen pulverförmigen oder pastenförmigen Reinigungsmitteln erforderlich, die in Form von konzentrierten wäßrigen Stammlösungen eingesetzt v/erden sollen, wie das z.B. bei modernen Strahlreinigungsgeräten oder Plüssig-Dosiergeräten der Fall ist.The use of solution brokers is required if such cleaning agents are produced as concentrated liquid preparations. They are also used in powder form or paste-like cleaning agents are required, which are used in the form of concentrated aqueous stock solutions v / should be grounded, as is the case, for example, with modern jet cleaning devices or Plüssig dosing devices.
6O9808/O97S6O9808 / O97S
Die Verwendung von Lösungsvermittlern ist dort vor allem erforderlich, weil die nichtionischen und anionischen Tenside in wäßrigen-, Gerüststoffe enthaltenden Lösungen nicht ausreichend löslich sind. Bereits bei relativ niedrigem Gehalt der wäßrigen Lösungen an" Gerüststoffen oder anderen Elektrolyten separieren die Tenside aus "der Lösung. Durch Zusatz geeigneter Lösungsvermittler gelingt es, die Löslichkeit dieser Tenside in wäßrigen Lösungen von Gerüststoffen zu verbessern. Als Lösungsvermittler für anionische Tenside sind bisher vor allem Alkalisalze von Paratoluolsulfonsäure, Xylolsulfonsäure und Cumolsulfonsäure bekannt geworden. Bekannte Lösungsvermittler für nichtionische Tenside sind primäre und sekundäre Phosphorsäureester von Fettalkoholpolyglykoläthern und Alkylphenolpolyglykoläthern (vgl. Soap and Chemical Specialities Mai 1969, Seiten 86 bis 93). Die hydrotropen Eigenschaften der bekannten LösungsVermittler sind jedoch nur schwach ausgeprägt und ihre Wirkung reicht nicht aus, um die zur Herstellung von Reinigungsmitteln-Konzentraten erforderlichen Mengen der Tenside in Gegenwart hoher Elektrolytkonzentrationen klar zu lösen bzw. zu dispergieren. So werden z.B., um etwa 3 Gewichtsteile eines nichtionischen Tensids in 100 Teilen eines wäßrigen Reinigungsmittel-Konzentrats entsprechend etwa der folgenden Zusammensetzung:The use of solubilizers, there is mainly required because the nonionic and anionic surfactants in aqueous -, builders containing solutions are not sufficiently soluble. Even with a relatively low content of "builders or other electrolytes" in the aqueous solutions, the surfactants separate from "the solution." By adding suitable solubilizers, it is possible to improve the solubility of these surfactants in aqueous solutions of builders. As solubilizers for anionic surfactants, alkali salts of paratoluene sulfonic acid, xylene sulfonic acid and cumene sulfonic acid in particular have become known so far. Known solubilizers for nonionic surfactants are primary and secondary phosphoric acid esters of fatty alcohol polyglycol ethers and alkylphenol polyglycol ethers (cf. Soap and Chemical Specialties May 1969, pages 86 to 93). However, the hydrotropic properties of the known solubilizers are only weakly pronounced and their effect is insufficient to clearly dissolve or disperse the amounts of surfactants required for the production of cleaning agent concentrates in the presence of high electrolyte concentrations. For example, around 3 parts by weight of a nonionic surfactant in 100 parts of an aqueous cleaning agent concentrate corresponding to the following composition:
Laurylalkoholnonaglykolather 3 TeileLauryl alcohol nonaglycol ether 3 parts
Natriumtripolyphosphat 10 TeileSodium tripolyphosphate 10 parts
Trinatriumphosphat 5 TeileTrisodium phosphate 5 parts
Natriummetasilikat 5 TeileSodium metasilicate 5 parts
Kaliumhydroxid 2 TeilePotassium hydroxide 2 parts
Wasser ■ 75 TeileWater ■ 75 parts
etwa 5 Gewichtsteile eines Phosphorsäuremono-Zdiesters von Nonylphenoltetraglykoläther oder eines Phosphorsäuremono-/diesters von Laurylalkoholtetraglykoläther benötigt. Zur Bereitung eines flüssigen Reinigungskonzentrates auf Basis eines anionischen Tensides wie die folgenden typischen Formulierungen anionischer Reiniger-Konzentrate zeigen, je nach Anteil des Pyrophosphat-Gerüststoffes 2 bzw. 10 Gewichtsprozent Natrium-paratoluolsulfonat eingesetzt werden.about 5 parts by weight of a phosphoric acid mono-zdiester of nonylphenol tetraglycol ether or a phosphoric acid mono / diester of lauryl alcohol tetraglycol ether is required. To prepare a liquid Cleaning concentrates based on an anionic surfactant such as the following typical formulations of anionic cleaning concentrates show, depending on the proportion of pyrophosphate builder 2 or 10 percent by weight of sodium paratoluenesulfonate can be used.
609808/0975 BAD ORIGINAL609808/0975 ORIGINAL BATHROOM
sek. Alkansulfonat-Natrium (C1, - C-g) . 10 % 10 % sec. Sodium alkanesulfonate (C 1 , - Cg). 10 % 10 %
Nonylphenoldekaglykoläther ~b % _ 3 % Nonylphenol decaglycol ether ~ b% _ 3 %
Kokosfettsäuremonoäthanolamidpentaglykoläthör 2 % 2 % Coconut fatty acid monoethanolamide pentaglycol ether 2% 2%
Tetrakaliumpyrophosphat ' 10 $ 20 % Tetrapotassium pyrophosphate '10 $ 20 %
p.-Toluolsulfonat-Natrium 2 %■' 10 % p.-toluenesulfonate sodium 2 % ■ '10%
Ammoniak - 1 % 1 % Ammonia - 1 % 1%
Wasser 72 % 5^ % Water 72 % 5 ^%
Die zur Stabilisierung der nichtiortisch'en und anionischen Waschrohstoffe in hohen Elektrolyt-Konzentrationen aufweisenden wäßrigen Lösungen erforderlichen Mengen dieser Lösungsvermittler sind, wie die vorstehenden Beispiele zeigen, beachtlich und führen zu einer negativen Beeinflussung der Eigenschaften der Reinigungsmittel, wie z.B. des Schaumverhaltens; sie stellen darüberhinaus eine zusätzliche Abwasserbelastung dar und verursachen außerdem erhebliche Kosten. . .The ones to stabilize the noniortisch'en and anionic washing raw materials In aqueous solutions having high electrolyte concentrations, amounts of these solubilizers are required, such as the above examples show considerable and lead to a negative influence on the properties of the cleaning agents, such as foaming behavior; They also represent an additional waste water pollution and also cause considerable Costs. . .
Es wurde nun gefunden, daß Verbindungen der'allgemeinen Formel IIt has now been found that compounds of the general formula I
R-P-OYR-P-OY
OX (I)OX (I)
in der R einen geradkettigen oder verzweigten Alkyl- oder Alkenylresfc mit 6 bis 1*1, vorzugsweise 8 bis 10 Kohlenstoffatomen, X und Y Wasserstoff, Alkali, den Ammoniumrest oder einen Äthanolaminrest " bedeuten, ausgezeichnete, den bekannten LösungsVermittlern überlegene hydrotrope Eigenschaften gegenüber nichtionischen und anionischen oberflächenaktiven Verbindungen besitzen und deshalb mit besonderem Vorteil als Lösungsvermittler zur Herstellung pulverförmiger oder flüssiger Reinigungsmittel-Konzentraten auf Basis nich'tionischer und/oder anionischer oberflächenaktiver Verbindungen geeignet sind..in which R is a straight-chain or branched alkyl or alkenyl residue with 6 to 1 * 1, preferably 8 to 10 carbon atoms, X and Y hydrogen, alkali, the ammonium residue or an ethanolamine residue " mean excellent, superior to the known solubilizers have hydrotropic properties towards nonionic and anionic surface-active compounds and therefore with particular advantage as a solubilizer for the production of powder or liquid cleaning agent concentrates Based on non-ionic and / or anionic surface-active compounds are suitable.
Die Erfindung betrifft weiterhin pulverförmige oder flüssige Reinigungsmittel-Konzentrate auf Basis anionischer, nichtionischer und/oder amphoterer oberflächenaktiver Verbindungen, die gekennzeichnet sind durch einen Gehalt an Phosphonsäurederivaten der allgemeinen Formel IThe invention further relates to powdery or liquid cleaning agent concentrates based on anionic, nonionic and / or amphoteric surface-active compounds characterized are due to a content of phosphonic acid derivatives of the general formula I.
98Ö8/Q9798Ö8 / Q97
.jf. 7437090 .jf. 7437090
ο Ηο Η
Il
R-P-OY (I)Il
RP-OY (I)
OXOX
in der R, X und Y die vorstehend genannten Bedeutungen besitzen.in which R, X and Y have the meanings given above.
Die Zusammensetzung der pulverförmigen oder flüssigen Reinigungsmittel-Konzentrate gemäß der Erfindung kann jedoch-nach dem Verwendungszweck in weiten Grenzen variieren. Der Gehalt der Reinigungsmittel-Konzentrate an Waschaktivsubstansen (WAS) d.h. der Gehalt an nichtionischen, anionischen und amphoteren Tensiden zusammengenommen, beträgt im allgemeinen etwa 1 bis 20, vorzugsweise 2 bis 12 Gewichtsprozent und ihr Gehalt an Phosphonsäurederivaten der Formel I etwa 0,5 bis 5> vorzugsweise 1,0 bis 3,0 Gewichtsprozent.The composition of powder or liquid detergent concentrates according to the invention, however, can vary within wide limits according to the intended use. The content of detergent concentrates of washing active substances (WAS), i.e. the content of nonionic, anionic and amphoteric surfactants taken together is generally about 1 to 20, preferably 2 to 12 percent by weight and their content of phosphonic acid derivatives of the formula I about 0.5 to 5> preferably 1.0 to 3.0 percent by weight.
Handelt es sich bei den Reinigungsmittel-Konzentraten der Erfindung um flüssige Einstellungen, so beträgt der Wassergehalt im allgemeinen etwa 65 bis 85 Gewichtsprozent. Diese flüssigen Konzentrate werden durchweg alkalisch, vorzugsweise auf pH-Werte im Bereich von etwa 8 bis 1Ü eingestellt.When the detergent concentrates of the invention are liquid formulations, the water content is generally about 65 to 85 percent by weight. These liquid concentrates are all alkaline, preferably adjusted to pH values in the range from about 8 to 1N.
Neben den nichtionischen, anionischen und/oder amphoteren Tensiden und den Phosphonsäurederivaten der Formel T enthalten die Reinigungsmittel-Konzentrate gemäß der Erfindung üblicherweise als Gerüstsubstanzen und Additive bezeichnete Produkte, wie sie z.B. in dem Standardwerk Schwartz. Perry, Berch, "Surface Active Agents and Detergents", Vol. 2, (1958), Seiten 288 bis 317 beschrieben sind. Der Anteil dieser Gerüstsubstanzen und Additive in den Reinigungsmittel-Konzentraten beträgt im allgemeinen bis zu 35 Gewichtsprozent, insbesondere 5 bis 30 Gewichtsprozent. Als solche Gerüstsubstanzen kommen vor allem Alkaliortho- und-polyphosphate wie z.B. Natriumtripolyphosphat, Natriumpyrophosphat, Natriummetaphosphat und die entsprechenden Kaliumsalze in Mengen bis zu etwa 25 Gew.-JS, vornehmlich 8 bis l8 Gew.-%, zur Anwendung. Weitere Zusatzstoffe dieser Art sind organische Komplexbildner, wie z.B. Alkalisalze von Ethylendiamintetraessigsäure, Trinatriumcitrat oder Alkalisalze der Nitrilotriessigsäure, die in Mengen bis zu etwa 20 Gew.-/?,In addition to the nonionic, anionic and / or amphoteric surfactants and the phosphonic acid derivatives of the formula T, the cleaning agent concentrates according to the invention usually contain products known as builders and additives, such as those in the standard work Schwartz. Perry, Berch, "Surface Active Agents and Detergents", Vol. 2, (1958), pages 288-317. The proportion of these builder substances and additives in the cleaning agent concentrates is generally up to 35 percent by weight, in particular 5 to 30 percent by weight. ,% On the application - as such builders are primarily Alkaliortho- and polyphosphates such as sodium tripolyphosphate, sodium pyrophosphate, sodium metaphosphate, and the corresponding potassium salts in amounts up to about 25 parts by weight JS, especially 8 to l8 wt.. Other additives of this type are organic complexing agents, such as alkali salts of ethylenediaminetetraacetic acid, trisodium citrate or alkali salts of nitrilotriacetic acid, which can be used in amounts of up to about 20% by weight.
8/09758/0975
insbesondere bis zu etwa 12 Gew.-5S3 in den Reinigungsmitteln enthalten sein können. Als solche Zusatzstoffe kommen ferner Alkalisilikate wie z.B. Natriummetalsilikat oder Natriumdi- oder trisilikat in Mengen bis zu etwa 10 Gew.-%s insbesondere bis zu etwa 8 Gew.-? in Betracht.in particular up to about 12 wt. 5S 3 can be contained in the cleaning agents. As such additives are also alkali metal silicates such as sodium silicate or sodium di or Metal trisilicate in amounts up to about 10 wt -.% S preferably up to about 8 wt? into consideration.
Niehtionogene, oberflächenaktive Produkte,· wie sie in den Reinigungsmittel-Konzentraten' gemäß der Erfindung enthalten sein können, werden z.B. beschrieben in dem Standardwerk Schwartz, Perry, Berch "Surface Active Agents and. Detergents", Vol. II, (1958), Seiten 120 bis 138. Bevorzugt verwendete niehtionogene Waschrohstoffe sind z.N.Nonionic, surface-active products, as found in cleaning agent concentrates' may be contained according to the invention, are described, for example, in the standard work Schwartz, Perry, Berch "Surface Active Agents and. Detergents", Vol. II, (1958), Pages 120 to 138. Non-ionogenic washing raw materials used with preference are currently
a. Alkylphenolpolyglykolätherj besonders solche mit 8 bis 12 Kohlenstoffatomen im Alkylrest und einem Gehalt an etwa 4 bis 15 Oxyäthyleneinheitenja. Alkylphenol polyglycol ethers especially those with 8 to 12 carbon atoms in the alkyl radical and a content of about 4 to 15 oxyethylene units
b. geradkettige oder verzweigte, primäre oder' sekundäre Alkyl-b. straight-chain or branched, primary or 'secondary alkyl
. polyglykoläther, besonders solche, deren Alkylreste etwa 8 bis 20 Kohlenstoffatome umfassen und die etwa 4 bis 20 Oxäthyleneinheiten im Molekül enthalten, " .. polyglycol ethers, especially those whose alkyl radicals are about 8 to Contain 20 carbon atoms and contain about 4 to 20 oxethylene units contained in the molecule, ".
c. Propylenoxid-Ä'thylenoxid-Blockpolymerisate, besonders die Anlagerungsverbindungen von etwa 5 bis 20 Molen Äthylenoxid an 1 Mol Propylenglykol vom Molgewicht von etwa 1800 bis 3000,c. Propylene oxide-ethylene oxide block polymers, especially the addition compounds from about 5 to 20 moles of ethylene oxide to 1 mole Propylene glycol with a molecular weight of about 1800 to 3000,
d. Alkylamin-Oxyäthylate, besonders, solche mit Alkylresten von etwa 10 bis 20 Kohlenstoffatomen und etwa 4 bis 15 A'thylenglykoläthergruppen im Molekül sowied. Alkylamine oxyethylates, especially those with alkyl radicals of about 10 to 20 carbon atoms and about 4 to 15 ethylene glycol ether groups in the molecule as well
■ . ι■. ι
e. Fettsäureoxäthylate, besonders solche mit Alkylresten von etwa 8 bis 20 Kohlenstoffatomen und etwa 4 bis 15 Oxyäthylenglykol-e. Fatty acid oxyethylates, especially those with alkyl radicals of about 8 to 20 carbon atoms and about 4 to 15 oxyethylene glycol
Xäthergruppen im Molekül. ■Xether groups in the molecule. ■
Als anionische oberflächenaktive Produkte kommen in den Reinigungsmittel-Konzentraten vor allem solche vom Sulfonat- oder Sulfattyp in Betracht. In erster Linie handelt es sich hierbei um Alkansulf onate, wie aus n-Alkanen durch Sulfogilorierung oder SuIfoxida-The cleaning agent concentrates are used as anionic surface-active products especially those of the sulfonate or sulfate type are considered. First and foremost, it is alkanesulf onates, such as from n-alkanes by sulfogiloration or sulfoxide
tion und anschließende Hydrolyse bzw. Neutralisation oder durch : Bisulfataddition an Olefine erhältlich sind, um Olefinsulfonate j wie sie beispielsweise durch Sulfonierung primärer oder sekundärer ! aliphatischer Monoolefine mit gasförmigem Schwefeltrioxid und anschließende alkalische oder saure Hydrolyse erhalten werden, sowie Alkylbenzolsulfonate, beispielsweise n-Dodecylbenzolsulfonat. Geeignet sind ferner ^- -SuIfofettsäureester, primäre und sekundäre Alkylsulfate sowie die Sulfate von äthoxylierten oder propoxylierten höhermolekularen Alkoholen. Ferner kommen Sulfate von äthoxylierten oder propoxylierten Fettsäureamiden und Alkylphenolen sowie Fettsäuretauride und Fettsäureesäthionate in Frage. Geeignete anionische Tenside sind weiterhin Alkaliseifen von Fettsäuren natürlichen oder synthetischen Ursprungs, z.B. die Natriumseifen von Kokos-, Palmkernoder Talgfettsäuren. Einen Überblick über die in Betracht kommenden anionischen Tensiden gibt beispielsweise das Standard, Schwartz, Perry, Berch "Surfa.ce Active Agents and Detergents" Vol. II, 1958 Seiten 25 bis 102. Die anionsichen Tenside können in Form der Natrium-, Kalium- oder Ammoniumsalze oder auch als Salze organischer Basen, wie Mono-, Di- oder Triäthanolamin, vorliegen.tion and subsequent hydrolysis or neutralization or by: bisulfate addition to olefins are obtainable to olefin sulfonates j as they are, for example, by sulfonation of primary or secondary! aliphatic monoolefins with gaseous sulfur trioxide and subsequent alkaline or acidic hydrolysis are obtained, as well as alkylbenzenesulfonates, for example n-dodecylbenzenesulfonate. Also suitable are ^ - -Sulfofatty acid esters, primary and secondary alkyl sulfates and the sulfates of ethoxylated or propoxylated higher molecular weight alcohols. Furthermore, sulfates of ethoxylated or propoxylated fatty acid amides and alkylphenols as well as fatty acid taurides and fatty acid ethionates are possible. Suitable anionic surfactants are also alkali soaps of fatty acids of natural or synthetic origin, for example the sodium soaps of coconut, palm kernel or tallow fatty acids. An overview of the possible anionic surfactants is, for example, the Standard, Schwartz, Perry, Berch "Surfa.ce Active Agents and Detergents" Vol. II, 1958 pages 25 to 102. The anionic surfactants can be in the form of sodium, potassium or ammonium salts or as salts of organic bases, such as mono-, di- or triethanolamine, are present.
Die als Bestandteile der Reinigungsmittel-Konzentrate in Betracht kommenden amphoteren Tenside werden z.B. in Surface Active Agents and Detergents in "Vol. II (1958), Seiten 138 bis 1^3 beschrieben. Solche Tenside sind beispielsweise Alkylbetaine und insbesondere Alky!sulfobetaine, z.B. das 3-(N,N-dimethyl-N-alkyla.mmonium)-propan-1-sulfonat. The amphoteric surfactants that can be used as components of the cleaning agent concentrates are used, for example, in Surface Active Agents and Detergents in "Vol. II (1958), pages 138-1 ^ 3. Such surfactants are, for example, alkyl betaines and in particular alkyl sulfobetaines, e.g. 3- (N, N-dimethyl-N-alkyla.mmonium) propane-1-sulfonate.
Die Reinigungsmittel-Konzentrate gemäß der Erfindung können ferner auch Alkalilaugen in Mengen bis zu etwa 15 Gew.-^, vornehmlich bis zu 8 Gew.-%s sowie erforderlichenfalls weitere übliche Hilfsstoffe enthalten.The detergent concentrates according to the invention can furthermore also alkali metal hydroxide solutions in amounts of up to about 15 wt .- ^, especially up to 8 wt -% s contained and, if necessary, further customary auxiliaries..
Die als Lösungsvermittler in den Reinigungsmittel-Konzentraten gemäß der Erfindung verwendeten Phosphonsäurederivate der Formel I weisen neben den hervorragenden hydrotropen Eigenschaften überraschenderweise auch eine gute Beständigkeit gegenüber Alkalilaugen auf; sie sind im allgemeinen in einer Konzentration von z.B. 10 g/lThe phosphonic acid derivatives of the formula I used as solubilizers in the cleaning agent concentrates according to the invention In addition to their excellent hydrotropic properties, they surprisingly also have good resistance to alkaline solutions on; they are generally at a concentration of e.g. 10 g / l
8/09758/0975
in einer 25 #igen Natronlauge bie Raumtemperatur noch klar löslich. Von besonderem technischen Interesse ist jedoch vor allem das Vermögen der genannten Phosphonsäurederivate, nichtionischen und anionischen oberflächenaktiven Produkten eine ausreichende Beständigkeit in salzhaltigen Lösungen und insbesondere auch in Lösungen . mit hohem Anteil an Natriumsalzen kondensierte Phosphorsäuren zu verleihen. Der Anteil des als Lcsungsvermittler verwendeten Verbindungen der Formel I in den Reinigungsmittel-Konzentraten gemäß der Erfindung wird insbesondere aus wirtschaftlichen Gründen so niedrig wie möglich gehalten. Durch eine ausreichende hydrotrope Wirkung der Verbindungen der Formel I erforderliche Menge ist in erster Linie von der Zusammensetzung der Konzentrate, besonders vom Ionengehalt an WAS und Elektrolyten abhängig. Im allgemeinen kann davon ausgegangen werden, daß bezogen auf die Gewichtsmenge an WAS, in Abhängigkeit von dem Elektrolytgehalt, etwa 1 bis 50 % der Phosphonsäurederivate der Formel I anzuwenden sind. Gegenüber den bisher bekannten Lösungsvermittlern besitzen die Phosphonsäurederivate der Formel I den Vorteil, daß sie sowohl für Reiniger auf Basis von nichtionischen Tensiden als auch für Reiniger auf Basis von anionsichen Tensiden geeignet sind. Mit den neuen Lösungsvermittlern gemäß der Erfindung lassen sich in vielen Fällen, z.B. bei Reinigern mit sehr hohen Elektrolytgehalten, auch dann noch beständige wäßrige Lösungen einstellen, wenn die bekannten Lösungsvermittler versagen. Die bessere Wirksamkeit der erfindungsgemäß verwendten Phosphonsäurederivate der Formel I zeigt sich auch darin, daß von ihnen im Vergleich zu den bekannten Lösungsvermittlern eine deutlich geringere Menge ausreicht, um vergleichbare Effekte zu erzielen.Clearly soluble in a 25 # sodium hydroxide solution at room temperature. Of particular technical interest, however, is above all the ability of the above-mentioned phosphonic acid derivatives, nonionic and anionic surface-active products, sufficient resistance in saline solutions and in particular also in solutions. to impart phosphoric acids condensed with a high proportion of sodium salts. The proportion of the compounds of the formula I used as solubilizers in the cleaning agent concentrates according to the invention is kept as low as possible, in particular for economic reasons. The amount required by a sufficient hydrotropic action of the compounds of the formula I is primarily dependent on the composition of the concentrates, in particular on the ionic content of WAS and electrolytes. In general, it can be assumed that, based on the amount by weight of WAS, depending on the electrolyte content, about 1 to 50 % of the phosphonic acid derivatives of the formula I are to be used. Compared to the previously known solubilizers, the phosphonic acid derivatives of the formula I have the advantage that they are suitable both for cleaners based on nonionic surfactants and for cleaners based on anionic surfactants. With the new solubilizers according to the invention it is possible in many cases, for example in the case of cleaners with very high electrolyte contents, to establish stable aqueous solutions even if the known solubilizers fail. The better effectiveness of the phosphonic acid derivatives of the formula I used according to the invention is also shown in the fact that, compared with the known solubilizers, a significantly smaller amount of them is sufficient to achieve comparable effects.
So werden z.B. bei der weiter oben genannten typischen Formulierung eines flüssigen Reinigungsmittel-Konzentrates auf Basis eines nichtionischen Tensids, bestehend aus For example, in the typical formulation mentioned above a liquid cleaning agent concentrate based on a nonionic surfactant, consisting of
3 Gewichtsteilen . Laurylalkoholnonaglykoäther j ' 10 Gewichtsteilen Pentanatriumphosphat 5 Gewichtsteilen' Trinatriumphosphat 5 Gewichtsteilen Natriummetasilikat 2 Gewichtsteilen Hydroxid3 parts by weight. Lauryl alcohol nonaglyco ether j '10 parts by weight of pentasodium phosphate 5 parts by weight of trisodium phosphate 5 parts by weight of sodium metasilicate 2 parts by weight of hydroxide
609-8 08/0975609-8 08/0975
undand
75 Gewichtsteilen Wasser anstelle von 5 Gewichtsteilen eines üblichen Lösungsvermittlers nur I1I Gewichtsteile n-Octanphosphonsäure benötigt um eine klare, stabile Lösung herzustellen.75 parts by weight of water instead of 5 parts by weight of a customary solubilizer only requires 1 1 parts by weight of n-octanephosphonic acid to produce a clear, stable solution.
In gleicher Weise werden für die vorstehend ebenfalls bereits erwähnten typischen Formulierungen von flüssigen Reinigungsmittel-Konzentraten auf Basis anionischer Tenside, wie die nachstehenden Zusammensetzungen zeigen, bei Verwendung von z.B. n-Octanphosphonsäuren gegenüber p-Toluolsulfonat-natrium auf nur die Hälfte oder weniger als die Hälfte an Lösungsvermittler benötigt:In the same way, the typical formulations of liquid cleaning agent concentrates also already mentioned above based on anionic surfactants, as the following compositions show, when using, for example, n-octanephosphonic acids compared to sodium p-toluenesulfonate to only half or less than half of solubilizers needed:
In der nachfolgenden Gegenüberstellung wird für einige Reinigungsmittel-Systeme die jeweils zur Bereitung klarer, stabiler Lösungen erforderliche Menge an Lösungsvermittlern nach dem Stand der Technik und gemäß der Erfindung aufgeführt. Bei den folgenden Reinigern handelt es sich um flüssige Einstellungen deren Zusammensetzungen zunächst ohne Berücksichtigung der Lösungsvermittler in Gewichtsprzenten angegeben sind. Die bei den Lösungsvermittlern aufgeführten Zahlen geben an, wieviel Prozent, bezogen auf das Gewicht der Lösungen des jeweiligen LösungsVermittlers erforderlich sind, um klare stabile Lösungen zu erzielen. Dabei bedeutet das Zeichen daß mit der angegebenen Menge des betreffenden Lösungsvermittlers klare Lösungen noch nicht erreicht werden konnten.The following comparison shows some cleaning agent systems the amount of solubilizers required in each case for the preparation of clear, stable solutions according to the prior art and listed according to the invention. The following cleaners are liquid settings and their compositions are initially given in percentages by weight without taking into account the solubilizers. Those listed under the solubilizers Numbers indicate how many percent, based on the weight of the solutions of the respective solubilizer, are required to to achieve clear stable solutions. The symbol means that with the specified amount of the solubilizer in question clear solutions could not yet be reached.
Beispiel 2, flüssige Reiniger Nonylphenolmonoglykoläther K11P2O7 Example 2, liquid cleaning agent nonylphenol monoglycol ether K 11 P 2 O 7
€09808/0975€ 09808/0975
243709Q243709Q
Lösungsvermittler:Solubilizer:
Mono-/Diphosphorsäureester von Nonylphenol- 5,6 10,0Mono- / diphosphoric acid esters of nonylphenol-5.6 10.0
monoglykoläther . ·monoglycol ether. ·
Natrium-Xylolsulfonat Kalium-Xylolsulfonat Natrium-Dodecyldiphenyläthersulfonat" Natrium-p-Toluolsulfonat Kalium-p-Toluolsulfonat n-Octanphosphorsäure n-Decanphosphorsäure n-Tetradecanphosphorsäure C8H17PO3HNaSodium xylene sulfonate potassium xylene sulfonate sodium dodecyldiphenyl ether sulfonate "sodium p-toluenesulfonate potassium p-toluenesulfonate n-octane phosphoric acid n-decane phosphoric acid n-tetradecane phosphoric acid C 8 H 17 PO 3 HNa
C8H17PO3Na2.C 8 H 17 PO 3 Na 2 .
C8H17PO3KH ·C 8 H 17 PO 3 KH
C8H17PO3HN(C2H4OH)3 CgH17PO HNH(C2H4OH)2 C 8 H 17 PO 3 HN (C 2 H 4 OH) 3 CgH 17 PO HNH (C 2 H 4 OH) 2
CgH17PO3HNH2C2H4OHCgH 17 PO 3 HNH 2 C 2 H 4 OH
Beispiel 3, flüssige Reiniger Cq-C11-Alkohol-heptaglykoläther
Na5P3°10
Na3PO4 Example 3, liquid cleaners C q -C 11 alcohol heptaglycol ether Na 5 P 3 ° 10
Na 3 PO 4
Lösungsvermittler: Natrium-p-Toluolsulfonat Natrium-Xylolsulfonat Mono-/Diphosphorsäureester eines C10-C 4 Alkohol-hexaglykoläthers n-Oktanphosphorsäure n-Dekanphosphorsäure n-TetradekanphosphorsäureSolubilizer: sodium p-toluenesulfonate sodium xylene sulfonate mono- / diphosphoric acid ester of a C 10 -C 4 alcohol hexaglycol ether n-octane phosphoric acid n-decane phosphoric acid n-tetradecane phosphoric acid
Beispiel 4, flüssiges Waschmittel C12-C1J- Alkohol-monoglykoläther
Kokosfettsäuremonoäthanolamidpentaglykoläther Natriumeitrat . 2 H3O
Na3SiO-,
KOHExample 4, liquid detergent C 12 -C 1 I alcohol monoglycol ether, coconut fatty acid monoethanolamide pentaglycol ether, sodium citrate. 2 H 3 O Na 3 SiO-,
KOH
6(19808/09756 (19808/0975
Lösungsvermittler:
Natrium-p-Toluolsulfonat
Natrium-Xylolsulfonat n-OktanphosphorsäureSolubilizer:
Sodium p-toluenesulfonate sodium xylene sulfonate n-octane phosphoric acid
243709Π243709Π
20,0 20,020.0 20.0
4,54.5
Beispiel 5, Druckstrahlreiniger Cq-C11-Alkohol-heptaglykolätherExample 5, pressure jet cleaner Cq-C 11 alcohol heptaglycol ether
Na PO11 Na PO 11
Na2SiO,Na 2 SiO,
Na2CONa 2 CO
AtfiylendiamintetraessigsaureAtfiylenediamine tetraacetic acid
5,05.0
10,0 5,0 5,0 3,0 1,010.0 5.0 5.0 3.0 1.0
Lösungsvermittler:
Natrium-p-Toluolsulfonat Natrium-Xylolsulfonat n-OktanphosphorsäureSolubilizer:
Sodium p-toluenesulfonate sodium xylene sulfonate n-octane phosphoric acid
17,0 20,017.0 20.0
3,53.5
Zur weiteren Erläuterung der Erfindung werden nachfolgend noch
Beispiele für flüssige und pulverförmige Reinigungsmittel-Konzentrate
gegeben. Die Konzentrate werden durch einfaches Mischen mit der Komponenten hergestellt. Die Prozentangaben bedeuten in allen
Fällen Gewichtsprozente.In order to further explain the invention, the following are also provided
Examples of liquid and powder detergent concentrates are given. The concentrates are made by simply mixing them with the components. In all cases, the percentages are percentages by weight.
Beispiel 6, flüssige Reiniger % Example 6, liquid detergent %
/0975/ 0975
?43709Γ)? 43709Γ)
Beispiel 7, flüssige ReinigerExample 7, liquid cleaners
C -C ^-Alkohol + 9 Mol AeO Na5P3O10 Na3SiO3 C -C ^ alcohol + 9 moles AeO Na 5 P 3 O 10 Na 3 SiO 3
n-Oktanphosphonsäuren-octane phosphonic acid
Wasserwater
Beispiel 8, pulverförmiger Dampfstrahl- und Hochdruckreiniger -Alkohol-pentaglykoläther 18,5 % Example 8, powdered steam jet and high-pressure cleaner - alcohol pentaglycol ether 18.5 %
24,7 % 24,7 % 24.7 % 24.7 %
Cq-C .Cq-C.
Na5P3O10 Na3PO4 Natriumwasserglas (VerhältnisNa 5 P 3 O 10 Na 3 PO 4 sodium water glass (ratio
Na2ONa 2 O
SiO2 = 1:3,3)SiO 2 = 1: 3.3)
n-Oktanphosphonsäuren-octane phosphonic acid
24,7 % 7,4 % 24.7 % 7.4 %
27 g dieses pulverförmigen Reinigers lösen sich in 73 g Wasser zu einer klaren stabilen Lösung.27 g of this powdery cleaner dissolve in 73 g of water to a clear stable solution.
Beispiel 9, Autoreiniger in PulverformExample 9, Powdered Car Cleaner
-Alkohol-heptaglykoläther 15,0 % -Alcohol heptaglycol ether 15.0 %
-Alkohol-pentaglykoläther-Alcohol pentaglycol ether
9 Il9 Il
C9"Cii C 9 " C ii
Na3PO4 ! Well 3 PO 4 !
Natriumsalz der Nitrilotriessigsäure KOH
n-OktanphosphonsäureSodium salt of nitrilotriacetic acid KOH
n-octane phosphonic acid
5,0 % 23,0 % 50,0 % 5.0 % 23.0 % 50.0 %
2,0 % 5,0 % 2.0 % 5.0 %
20 g dieses Reinigers lösen in 80 g Wasser zu einer klaren stabilen Lösung.20 g of this cleaner dissolve in 80 g of water to form a clear, stable one Solution.
Beispiel 10, Druckstrahlreiniger in Pulverform Cq-C11-Alkohol-heptaglykoläther 12,0 % CQ-C11-Alkohol-pentaglykolätherExample 10, pressure jet cleaner in powder form C q -C 11 alcohol heptaglycol ether 12.0 % C Q -C 11 alcohol pentaglycol ether
Na5P3O10 Na3PO4 sekundäres C^-C^-Alkansulfonatnatrium Na 5 P 3 O 10 Na 3 PO 4 C 1 -C 4 secondary alkanesulfonate sodium
KOHKOH
6,0 % 50,0 % 20,0 % 6.0 % 50.0 % 20.0 %
5,0 % 2,0 % 5.0 % 2.0 %
β 0 9808/097 S-β 0 9808/097 S-
n-Oktanphosphonsäure 5,0 % n-octane phosphonic acid 5.0%
10 g dieses Reinigers lösen sich in 90 g Wasser zu einer klaren stabilen Lösung.10 g of this cleaner dissolve in 90 g of water to form a clear, stable solution.
Beispiel 11, pulverförmiger Geschirreiniger für Spulautomaten (Angaben in Gew.-%) Example 11, powdery dishwashing detergent for automatic winder (data in% by weight )
Na5P3O10 38,1 38,1 38,1 38,1Na 5 P 3 O 10 38.1 38.1 38.1 38.1
Na3PO4 15,9 15,9Na 3 PO 4 15.9 15.9
Na3PO4 . 10 H2O - -' 15,9 15,9Na 3 PO 4 . 10 H 2 O - - '15.9 15.9
Na2SiO3 24,3 24,3Na 2 SiO 3 24.3 24.3
Na2SiO3 . 5 H2O - - 25,3 25,3Na 2 SiO 3 . 5 H 2 O - - 25.3 25.3
KOH 6,4 6,4 6,4 6,4KOH 6.4 6.4 6.4 6.4
Tensid 1 3,2 - 3,2Surfactant 1 3.2-3.2
Tensid 2 - 3,2 - 3,2Surfactant 2 - 3.2 - 3.2
Kalium-Dichloriso-Potassium dichloroiso-
cyanurat 1,0 1,0cyanurate 1.0 1.0
n-Oktanphosphonsäure 11,1 11,1 11,1 11,1n-octanephosphonic acid 11.1 11.1 11.1 11.1
klare, stabile wäßrige Lösungen dieser Reiniger lassen sich herstellen bis
zu folgenden Maximalkonzentrationenclear, stable aqueous solutions of these cleaners can be produced up to
to the following maximum concentrations
20 % 25 % 30 % 30 % 20 % 25 % 30 % 30 %
Tensid 1 = Anlagerungsverbindung von 4 Molen Äthylenoxid an 1 Mol eines Polypropylenglykols vom Molgewicht I8OOSurfactant 1 = addition compound of 4 moles of ethylene oxide and 1 mole of a polypropylene glycol with a molecular weight of 180
Tensid 2 = Umsetzungsprodukt von 1 Mol eines C10-C14-Fettalkohols mit 15 Molen Propylenoxid und 12 Molen Äthylenoxid.Surfactant 2 = reaction product of 1 mole of a C 10 -C 14 fatty alcohol with 15 moles of propylene oxide and 12 moles of ethylene oxide.
(609808/0975(609808/0975
Claims (1)
R-P-OY (I)O
RP-OY (I)
Priority Applications (19)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE2437090A DE2437090A1 (en) | 1974-08-01 | 1974-08-01 | CLEANING SUPPLIES |
US493953A US3929678A (en) | 1974-08-01 | 1974-08-01 | Detergent composition having enhanced particulate soil removal performance |
NL7508895A NL7508895A (en) | 1974-08-01 | 1975-07-25 | CLEANERS. |
AT581175A AT344301B (en) | 1974-08-01 | 1975-07-28 | CLEANING SUPPLIES |
CH988275A CH614462A5 (en) | 1974-08-01 | 1975-07-29 | Cleaner concentrate |
DE2533758A DE2533758C2 (en) | 1974-08-01 | 1975-07-29 | laundry detergent |
GB31887/75A GB1522981A (en) | 1974-08-01 | 1975-07-30 | Detergent compositions |
LU73103A LU73103A1 (en) | 1974-08-01 | 1975-07-30 | |
IT25934/75A IT1040248B (en) | 1974-08-01 | 1975-07-30 | MEANS OF CLEANING |
NL7509077A NL7509077A (en) | 1974-08-01 | 1975-07-30 | METHOD FOR PREPARING A DETERGENT WITH A STRONG, DISTRIBUTED SOIL-REMOVING EFFECT. |
JP50092622A JPS5137902A (en) | 1974-08-01 | 1975-07-31 | |
FR7523931A FR2280706A1 (en) | 1974-08-01 | 1975-07-31 | CLEANING AGENT CONCENTRATES |
BE158838A BE831995A (en) | 1974-08-01 | 1975-07-31 | DETERGENT COMPOSITION WITH IMPROVED PERFORMANCE IN THE REMOVAL OF SPECIAL SOILS |
DK348875A DK348875A (en) | 1974-08-01 | 1975-07-31 | POWDERED OR LIQUID ADMINISTRATED CLEANING CONCENTRATES AND PROCEDURES FOR THE PREPARATION |
IE1713/75A IE41438B1 (en) | 1974-08-01 | 1975-07-31 | Detergent compositions |
FR7524026A FR2280705A1 (en) | 1974-08-01 | 1975-07-31 | DETERGENT COMPOSITION WITH IMPROVED PERFORMANCE IN THE REMOVAL OF SPECIAL SOILS |
GB32084/75A GB1507083A (en) | 1974-08-01 | 1975-07-31 | Detergent composition having enhanced particulate soil removal performance |
BE158875A BE832048A (en) | 1974-08-01 | 1975-08-01 | CLEANING AGENT CONCENTRATES |
SE7508754A SE7508754L (en) | 1974-08-01 | 1975-08-01 | CLEANER |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE2437090A DE2437090A1 (en) | 1974-08-01 | 1974-08-01 | CLEANING SUPPLIES |
US493953A US3929678A (en) | 1974-08-01 | 1974-08-01 | Detergent composition having enhanced particulate soil removal performance |
Publications (1)
Publication Number | Publication Date |
---|---|
DE2437090A1 true DE2437090A1 (en) | 1976-02-19 |
Family
ID=25767502
Family Applications (2)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
DE2437090A Pending DE2437090A1 (en) | 1974-08-01 | 1974-08-01 | CLEANING SUPPLIES |
DE2533758A Expired DE2533758C2 (en) | 1974-08-01 | 1975-07-29 | laundry detergent |
Family Applications After (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
DE2533758A Expired DE2533758C2 (en) | 1974-08-01 | 1975-07-29 | laundry detergent |
Country Status (7)
Country | Link |
---|---|
US (1) | US3929678A (en) |
BE (2) | BE831995A (en) |
DE (2) | DE2437090A1 (en) |
FR (2) | FR2280706A1 (en) |
GB (1) | GB1507083A (en) |
LU (1) | LU73103A1 (en) |
NL (2) | NL7508895A (en) |
Families Citing this family (1289)
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Family Cites Families (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
GB1119884A (en) * | 1966-06-13 | 1968-07-17 | Unilever Ltd | Controlled sudsing compositions |
CA813301A (en) * | 1966-09-06 | 1969-05-20 | E. Zimmerer Roger | Detergent composition |
BE754502A (en) * | 1969-08-07 | 1971-01-18 | Bayer Ag | PROCESS FOR DYING NITROGENOUS FIBROUS MATERIALS |
GB1315363A (en) * | 1970-05-29 | 1973-05-02 | Unilever Ltd | Liquid detergents |
GB1441588A (en) * | 1972-10-04 | 1976-07-07 | Unilever Ltd | Rinse composition |
-
1974
- 1974-08-01 DE DE2437090A patent/DE2437090A1/en active Pending
- 1974-08-01 US US493953A patent/US3929678A/en not_active Expired - Lifetime
-
1975
- 1975-07-25 NL NL7508895A patent/NL7508895A/en not_active Application Discontinuation
- 1975-07-29 DE DE2533758A patent/DE2533758C2/en not_active Expired
- 1975-07-30 NL NL7509077A patent/NL7509077A/en not_active Application Discontinuation
- 1975-07-30 LU LU73103A patent/LU73103A1/xx unknown
- 1975-07-31 FR FR7523931A patent/FR2280706A1/en active Granted
- 1975-07-31 BE BE158838A patent/BE831995A/en not_active IP Right Cessation
- 1975-07-31 FR FR7524026A patent/FR2280705A1/en active Granted
- 1975-07-31 GB GB32084/75A patent/GB1507083A/en not_active Expired
- 1975-08-01 BE BE158875A patent/BE832048A/en unknown
Also Published As
Publication number | Publication date |
---|---|
FR2280705B1 (en) | 1978-10-13 |
NL7508895A (en) | 1976-02-03 |
LU73103A1 (en) | 1977-03-24 |
GB1507083A (en) | 1978-04-12 |
DE2533758C2 (en) | 1984-03-01 |
FR2280706A1 (en) | 1976-02-27 |
FR2280706B1 (en) | 1978-12-08 |
BE832048A (en) | 1976-02-02 |
NL7509077A (en) | 1976-02-03 |
US3929678A (en) | 1975-12-30 |
BE831995A (en) | 1976-02-02 |
DE2533758A1 (en) | 1976-02-12 |
FR2280705A1 (en) | 1976-02-27 |
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