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WO1996000253A1 - Composition tensioactive contenant un produit d'addition acetal ou cetal - Google Patents

Composition tensioactive contenant un produit d'addition acetal ou cetal Download PDF

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Publication number
WO1996000253A1
WO1996000253A1 PCT/US1995/007886 US9507886W WO9600253A1 WO 1996000253 A1 WO1996000253 A1 WO 1996000253A1 US 9507886 W US9507886 W US 9507886W WO 9600253 A1 WO9600253 A1 WO 9600253A1
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WIPO (PCT)
Prior art keywords
acetal
composition
weight
percent
independently
Prior art date
Application number
PCT/US1995/007886
Other languages
English (en)
Inventor
Mark S. Felix
Original Assignee
The Dow Chemical Company
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by The Dow Chemical Company filed Critical The Dow Chemical Company
Priority to AU28695/95A priority Critical patent/AU2869595A/en
Publication of WO1996000253A1 publication Critical patent/WO1996000253A1/fr

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Classifications

    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
    • A61K8/39—Derivatives containing from 2 to 10 oxyalkylene groups
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
    • A61K8/84—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds obtained by reactions otherwise than those involving only carbon-carbon unsaturated bonds
    • A61K8/86—Polyethers
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q19/00—Preparations for care of the skin
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01D—SEPARATION
    • B01D19/00—Degasification of liquids
    • B01D19/02—Foam dispersion or prevention
    • B01D19/04—Foam dispersion or prevention by addition of chemical substances
    • B01D19/0404—Foam dispersion or prevention by addition of chemical substances characterised by the nature of the chemical substance
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
    • C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
    • C08G65/32—Polymers modified by chemical after-treatment
    • C08G65/329—Polymers modified by chemical after-treatment with organic compounds
    • C08G65/331—Polymers modified by chemical after-treatment with organic compounds containing oxygen
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K3/00—Materials not provided for elsewhere
    • C09K3/32—Materials not provided for elsewhere for absorbing liquids to remove pollution, e.g. oil, gasoline, fat
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K8/00—Compositions for drilling of boreholes or wells; Compositions for treating boreholes or wells, e.g. for completion or for remedial operations
    • C09K8/02—Well-drilling compositions
    • C09K8/32—Non-aqueous well-drilling compositions, e.g. oil-based
    • 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
    • C11D1/825—Mixtures of compounds all of which are non-ionic
    • C11D1/8255—Mixtures of compounds all of which are non-ionic containing a combination of compounds differently alcoxylised or with differently alkylated chains
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
    • A61K2800/40—Chemical, physico-chemical or functional or structural properties of particular ingredients
    • A61K2800/59—Mixtures
    • A61K2800/596—Mixtures of surface active 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
    • C11D1/66—Non-ionic compounds
    • C11D1/72—Ethers of polyoxyalkylene glycols
    • C11D1/721—End blocked ethers

Definitions

  • This invention relates to surfactants and more particularly to compositions which comprise a polyoxyalkylene acetal or ketal, and a process for preparing the same.
  • surfactants Products having surface active properties, commonly called surfactants or stabilizing agents, are widely used in many industrial, agricultural and pharmaceutical applications where it is necessary to modify hydrophobic/hydrophilic surface interactions.
  • Frequently employed surfactants include liquid polyoxyalkylene polymers and silicon-based polyoxyalkylene polymers.
  • surfactant product which possesses a greater activity and therefore could be deployed in smaller amounts to achieve the same technical result. Use of smaller amounts would lead to a significantly reduced environmental accumulation potential.
  • a surfactant which exhibits a greater activity in the application area and which further has an attractive degree of biodegradability.
  • Certain substances are known from the art to have surfactant activities and additionally exhibit some biodegradability, such substances include ketals and acetals as discussed in the patent document EP-A-512,501.
  • the preparation of alternative surfactants comprising acetal adducts has been investigated with a view to obtaining an enhanced surfactant activity and eventually enhanced biodegradability.
  • the assessment of surface activity can be conveniently determined by observing the change of surface tension of water with concentration of the adduct. When, upon addition of the adduct, the surface tension of water ceases to change (normally decrease) the critical micelle concentration (CMC) forthe adduct has been attained. A lower CMC value is taken as indicating a greater surface activity.
  • CMC critical micelle concentration
  • acetals or ketals may be obtained by reacting an alcohol with a vi nyl ether or olefi n.
  • U.S. Patent 3,024,284 d iscl oses a process for the preparati on of si m pie ketals by reacting a lower secondary alcohol with an alpha-unsaturated ether in the presence of an acid catalyst.
  • U.S. Patent 3,931 ,337 discloses the preparation of multiblock polyacetal copolymer surfactants by reacting a polyoxyalkylene polymer with a lower alkyl vinyl ether followed by thermal coupling of the acetal-terminated polymers to give the final product.
  • Patent 3,954,886 discloses the preparation of polyoxyethylene acetal surfactants by the sequential reaction of polyoxyethylene diols with a high molecular weight alkyl vinyl ether followed by a low molecular weight alkyl vinyl ether.
  • U.S. Patent 3,244,753 discloses the preparation of acetals of mono- and polyoxyalkylene glycols with vinyl ethers in the presence of an acid catalyst and specific phosphorus compounds to prevent the formation of colored products.
  • U.S. Patent 2,905,719 discloses the preparation of acetal surfactants by reacting vinyl ethers containing from 8 to 18 carbon atoms with ethoxylated alcohols.
  • German patent DE 22 52 186 discloses the preparation of a surfactant by reacting a polyoxyalkylene polyoi, predominantly oxypropylene, with an excess of an alkyl vinyl ether in the presence of an acid catalyst.
  • acetal/ketal surfactants there is still a need to develop alternative products with a view to optimizing activity and/or biodegradability properties.
  • the present invention is a composition comprising a hydroxyl-
  • the acetal or ketal present in an amount of from 1 to 99 percent by weight based on total parts by weight of the composition, is an adduct of a monohydroxyl-terminated polyoxyalkylene; and b) the composition exhibits a critical micelle concentration (CMC) in water of less than 25 ppm of water at 25°C.
  • CMC critical micelle concentration
  • the present invention is a fatty alcohol alkoxylate composition which contains from 1 to 99 parts per 100 parts by total weight of the composition of an acetal mixture comprising components (a) and (b) wherein said mixture is characterized in that, based on the total parts by weight of (a) and (b) present, it comprises: a) from 1 to 99 weight percent of a substance corresponding to Formula (I), and
  • F is independently a hydrocarbyl radical having from 6 to 30 carbon atoms
  • AO is independently a C 2 -4 oxyalkylene moiety where more than 50 mole percent of the oxyalkylene moiety is a C 2 substance
  • n is independently a number of from 3 to 30
  • R is a hydrocarbyl radical having from 1 to 5 carbon atoms.
  • the present invention is a process for preparing a fatty alcohol alkoxylate, as mentioned above, characterized in that a monohydroxyl-terminated polyoxyalkylene or fatty alcohol alkoxylate is reacted, in the presence of an acid catalyst, with an alkyl vinyl ether present in an amount to provide from 0.05 to 0.98 equivalents per hydroxyl group.
  • this invention relates to the following methods and formulations of industrial relevance using one of the above-mentioned compositions, to modify any hydrophilic/hydrophobic or lipophilic/iipophobic interaction, including:
  • a method for stabilizing oil or gas well walls which comprises using an invert- -emulsion or emulsion drilling mud wherein the invert-emulsion drilling mud contains from 0.5 to 100 percent by weight, and the emulsion drilling mud includes from 0.5 to 50 percent by weight, of one of the above-mentioned compositions.
  • a method for controlling foam formation of an aqueous or non aqueous mixture in an environment with free surface turbulence which comprises bringing said mixture into contact with from 0.0001 to 10 percent by weight of one of the above-mentioned compositions.
  • Exemplary of situations where control of foam formation is desirable include the paper, pulp and food processing industries.
  • a method for cleaning which comprises bringing a surface to be cleaned into contact with a cleansing agent which includes one of the above-mentioned compositions.
  • a cleansing agent which includes one of the above-mentioned compositions.
  • Particular examples of such a method are the industrial cleaning methods for dairy or brewery equipment.
  • a method for dispersing oil spills on water which comprises treating an oil- contaminated water surface with a dispersing agent that includes one of the above-mentioned compositions.
  • a cleaning formulation in particular a laundry detergent, which comprises a component being one of the above-mentioned compositions.
  • a cosmetic formulation which comprises one of the above-mentioned compositions.
  • a pesticide formulation comprising an active component such as a herbicide, insecticide, fungicide, or bactericide, and a further component being one of the above- -mentioned compositions.
  • composition of this invention A pharmaceutical formulation containing a physiologically active component and a further component being one of the above-mentioned compositions.
  • the attractive surface activity and biodegradability properties of the composition of this invention allows it to conveniently substitute for many of the nonionic surfactants, especially oxyalkylene adducts of fatty alcohols, presently used in industry.
  • the composition of this invention comprising a hydroxyl-terminated polyoxyalkylene and an acetal or ketal adduct of a monohydroxyl-terminated polyoxyalkylene exhibits a critical micelle concentration (CMC) in water of less than 25, preferably less than 20, more preferably less than 15, and yet more preferably less than 10 ppm of water at 25°C.
  • CMC critical micelle concentration
  • Such CMC performance can be obtained with a composition which, based on total parts by weight of the composition, comprises from 1 to 99 percent by weight of adduct, preferably an acetal adduct.
  • the adduct is present in an amount of from 5, more preferably from 10, yet more preferably from 15, and yet still more preferably from 20 weight percent; and preferably up to 95, more preferably up to 90, yet more preferably up to 80, and yet still more preferably up to 60 weight percent.
  • the balance of the composition is a hydroxyl-terminated polyoxyalkylene, and particularly a monohydroxyl-terminated polyoxyalkylene such as, for example, an oxyalkylene derivative of an aliphatic fatty alcohol, optionally unsaturated.
  • the provision of a limited acetal/ketal content of the composition is desirable to provide for an enhanced biodegradability and, a reduction of potential aquatic toxicity.
  • the acetal/ketal content also provides the composition with a better resistance to basic conditions rendering it especially suitable for applications where attractive stability under basic conditions is desirable.
  • the composition comprises an acetal mixture which, based on the total parts by weight of components (a) and (b) present, comprises: a) from 1 to 99 weight percent of a first acetal substance corresponding to
  • CH 3 wherein, is independently a hydrocarbyl radical, optionally unsaturated, having from 6 to 30 carbon atoms;
  • AO is independently a C 2- 4 oxyalkylene moiety, and preferably where more than 50 mole percent of the oxyalkylene moiety is a C 2 substance; n is independently a number of from 3 to 30; and R is a hydrocarbyl radical having from 1 to 5 carbon atoms. Further to the first and second acetal substance, the mixture may additionally contain a third acetal substance corresponding to Formula (III): R - O - CH - O - R
  • the third acetal substance may be present in an amount of from 0.1 to 15 weight percent of the total acetal mixture comprising the first, second and third acetal substances.
  • the acetal mixture advantageously contains the first acetal substance preferably in an amount of from 5, more preferably from 20, and yet more preferably from 40; and preferably up to 95, more preferably up to 80 and yet more preferably up to 60 weight percent.
  • the acetal mixture advantageously contains the second acetal substance 0 preferably in an amount of up to 95, more preferably up to 80 and yet more preferably up to
  • the hydrocarbyl radical F advantageously is a linear group which preferably contains from 8, and preferably up to 25, -> more preferably up to 18, and yet more preferably up to 15 carbon atoms. Carbon-carbon unsaturation may also be present within the hydrocarbyl radical F.
  • the hydrophobic/lipophiiic nature conferred by the presence of the hydrocarbyl radical F should be complimented by a hydrophilic/lipophobic moiety, in this case the oxyalkylene chain of limited length.
  • the value "n" preferably is from 5, more preferably from 7, and preferably up to 20, and more preferably up to 12.
  • the hydrocarbyl radical F contains from 8 to 12 carbon atoms, and the value "n" is from 7 to 12.
  • the hydrocarbyl radical R can be any (cyclo) alkane.
  • the hydrocarbyl radical R preferably comprises from 1 to 5 carbon atoms and advantageously is a * or C5 radical, including the n- or i-isomers of butyl or pentyl radicals.
  • the remaining part of the composition is a hydroxyl-terminated polyoxyalkylene which is a polyoi or, preferably, a monohydroxyl substance.
  • a hydroxyl-terminated polyoxyalkylene which is a polyoi or, preferably, a monohydroxyl substance.
  • the hydroxyl-terminated ⁇ polyoxyalkylene is a monohydroxyl substance, it is advantageously an oxyalkylene derivative of a fatty alcohol having the general formula:
  • this invention also relates to a process for the preparation of the 5 above-described composition comprising a ketal, or preferably acetal, adduct by reacting a limited amount of an alkyl vinyl ether with a monohydroxyl-terminated polyoxyalkylene in the presence of an acid catalyst.
  • the amount of alkyl vinyl ether present in the process is up to a stoichiometric equivalent per hydroxyl group of the monohydroxyl-terminated polyoxyalkylene.
  • the amount of vinyl ether is from 0.05, preferably from 0.1, more preferably from 0.15, and yet more preferably from 0.2; and preferably up to 0.98, more preferably up to 0.95, yet more preferably up to 0.8, and still more preferably up to 0.75 equivalents per hydroxyl group of the polyoxyalkylene. It is presently understood that the alkyl vinyl ether reacts with the monohydroxyl-terminated polyoxyalkylene to provide an acetal corresponding to Formula (II) which, under the acidic process conditions and elevated temperature, subsequently undergoes transacetalization to provide acetal corresponding to Formula (I) and Formula (III).
  • acetal corresponding to Formula (III) may be volatile and susceptible to removal under the conditions employed to manufacture the composition.
  • the end composition may not contain acetal (I) and acetal (III) type components in commensurate proportions.
  • reaction temperature is, advantageously, at least 30°C, preferably from 30°C to 100°C, and more preferably from 40 C C to 80°C.
  • reaction temperature is, advantageously, at least 30°C, preferably from 30°C to 100°C, and more preferably from 40 C C to 80°C.
  • an undesirable color of the composition can result. It is found that under the acid catalyzed conditions and elevated temperature that reaction of the vinyl ether proceeds relatively quickly and that addition times ranging from a few minutes to 10 hours, and typically from 10 minutes to 2 hours provide for essentially complete conversion of the vinyl ether. It is observed that higher rates of addition of the vinyl ether generally favor the transacetalization reaction.
  • Suitable monohydroxyl-terminated polyoxyalkylene substances for use in the process include an oxyalkylene adduct of a fatty alcohol having the formula:
  • the AO moiety advantageously comprises a majority of C 2 , oxyethylene, units.
  • the monohydroxyl-terminated polyoxyalkylene contains a hydrophobic substituent having from 6 to 30 carbon atoms.
  • Oxyalkylated fatty alcohols are generally commercially available and obtained bythe reaction of a fatty alcohol with an alkylene oxide including notably propylene oxide, butylene oxide and especially ethylene oxide, usually in the presence of an alkaline catalyst.
  • Oxyalkylated fatty alcohols particularly well suited for use in the process of this invention are those which do not have any appreciable free salt content, as can be acquired by the in situ acid treatment of the alkali catalyst used in the manufacture of the oxyalkylated fatty alcohol.
  • the presence of an appreciable amount of free salt can be detrimental to the formation of acetal and eventual effectiveness of the composition in the chosen application area. If free salt is present, it is, advantageously, less than 100 ppm, and preferably less than 50 ppm of oxyalkylated fatty alcohol.
  • Suitable alkyl vinyl ethers for use in the process correspond to those having the general formula:
  • R - O - CHY - CH 2 (V) wherein R is as mentioned above; and Y, when intending to prepare an acetal adduct is hydrogen and, when intending to prepare a ketal can be any (cyclo) alkyl, aryl or heterocyclic radical but advantageously is a C C 6 alkyl or aryl radical.
  • the reaction takes place in the presence of an acid catalyst.
  • acid catalyst can be a free acid, such as for example p-toluene sulphonic acid.
  • the acid catalyst is present on a fixed bed in which case an acidic ion-exchange resin can be employed to advantage.
  • the final acetal/ketal content of the so obtained composition could be modified by subsequently adding a desired amount of a hydroxyl-terminated polyoxyalkylene free of any acetal/ketal substances.
  • the desired composition could be obtained by blending a pure acetal or ketal substance(s) with a hydroxyl-terminated polyoxyalkylene free of any acetal/ketal substance in the appropriate proportions.
  • Acetal-containing compositions, Compositions 1 to 4 are prepared according to the following general procedure. Amounts of substances where not mentioned in the general procedure are identified in Table I. A reactor is charged with a given amount of an alkoxylated fatty alcohol (FAE) represented bythe formula C ⁇ oO-(C 2 H 4 0-) H, and 3.1 parts by weight of an acidic ion- -exchange resin DOWEX 50 W8 available from The Dow Chemical Company. The resulting mixture is brought to a temperature of 105°C at a reduced pressure of lO mbar and maintained under these conditions for approximately 2 hours to minimize any water content.
  • FAE alkoxylated fatty alcohol
  • the "dried" mixture is then broughtto 50°C and ambient pressure, under nitrogen, prior to introducing a given amount of isobutyl vinyl ether (IBVE).
  • IBVE isobutyl vinyl ether
  • the IBVE is introduced in one portion with continuous agitation of the mixture.
  • the resulting reaction product is filtered to remove acidic ion-exchange resin providing a pale yellow to colorless acetal-containing composition.
  • Certain physical properties of the resulting acetals compositions are reported in Table I along with the relative concentrations of the acetals corresponding to Formulae I, II, and 111 as observed by 13 C NMR (CD 3 COCD 3 ). The physical properties are observed according to the following test procedures, for: wetting times DIN 53901 ; foam behavior according to the "Ross-Miles" test, ASTM-D-1173; and aqueous cloud point, ASTM D-2024.
  • CMC critical micelle concentration
  • Composition 5 is prepared according to the above general procedure with reactants in the proportions as indicated for Composition 2 except, in this instance, the total amount of IBVE is added in small increments over a period of 30 minutes and the resulting mixture stirred for a further 30 minutes prior to removing the ion-exchange resin.
  • Compositional analysis and physical properties of Composition 5 are also reported in Table I.
  • the pour point temperature of the composition increases with decreasing total acetal content of the composition. Better foam control is exhibited by compositions having a higher total acetal content.
  • the cloud point temperature of the composition generally increases with decreasing total acetal content of the composition.
  • the cloud point can be significantly influenced bythe distribution of the different acetal components.
  • Composition 5 has approximately the same total acetal content as that of Composition 2 and yet exhibits a significantly higher cloud point temperature. The ability to influence cloud point in such a manner enhances the value of the compositions for applications where susceptibility to unwanted, unattractive, turbidity may be encountered.
  • biodegradability of substances is evaluated in an aerobic aqueous medium with the Manomeric Respirometry test according to published OECD Guidelines for testing of Chemicals Number 301 F and Method C.4-D in Commission Directive 92/69/EEC. Substances are considered as being readily biodegradable if the extent of biodegradation is more than 60 percent after 28 days.
  • compositions 2 and 4 Based on oxygen consumption after 28 days, Compositions 2 and 4 exhibited a biodegradability ranging from 72 to 81 percent. By way of comparison in the same evaluation, a representative commercially available oxyethylene-oxypropylene C ⁇ 3 -fatty alcohol having an oxyethylene:oxypropylene weight ratio of 85: 15 exhibits a biodegradability of 34 percent. Table I
  • composition pbw mole eq. composition different acetals (°c) (°C) (sec) (mm) (ppm)
  • compositions of this invention for cleaning applications, where additional control of foam formation can be important, is demonstrated by the following example where the compositions are used to substitute for a standard nonionic surfactant in a typical all-purpose cleaning formulation.
  • the performance of the cleaning formulation is observed according to the industrially accepted Industrie notion fuerPutz and Vietnamesestoff (IPP) test.
  • a weighted sponge having absorbed on to it the cleaning solution is mechanically moved backwards and forwards (a total of 10 passes) over a soiled substrate, which has also been wetted with the o cleaning solution.
  • the cleaned substrate is then washed in running water before it is measured for comparative cleanliness.
  • the "soiling" of the substrate, a clear plastic strip to which a wrinkled, white, PVC strip has been attached, consists of carbon black and oleochemicals.
  • the cleaning efficiency, of the formulation is determined by measuring the whiteness of the cleaned substrate via the reflectance of light and comparing it to that of the original surface. 5
  • the foam control potential of the formulation is demonstrated by a modified
  • DOWANOL DPM an oxypropylene adduct of methanol, available 0 from The Dow Chemical Company
  • DOWANOL DPnB an oxypropylene adduct of butanol, available from The Dow Chemical Company
  • Example 4 the value of the compositions of this invention as nonionic surfactants in a typical hard surface cleaner can be demonstrated.
  • Atypical hard surface cleaner formulation is given below, the nonionic surfactant is as given in Table III.
  • Comparative Surfactant C representative of a typical commercially employed nonionic surfactant is
  • DOWFAX 20A64 an oxypropylene-oxyethylene adduct of a fatty alcohol, available from The Dow Chemical Company.
  • DOWANOL DB an oxyethylene adduct of butanol, available from The Dow Chemical Company 2.6 Nonionic surfactant, see Table III
  • Example6 0 Many cleaning formulations require the presence of a nonionic with an anionic surfactant to provide for an optimum performance. In such formulations it is frequently highly desirable to control and minimize foam formation and/or its persistence. This example demonstrates, by use of the above described modified Ross-Miles Test, the surprisingly good ability of the compositions of the invention to provide for foam control of a formulation -> comprising an anionic and nonionic surfactant.
  • composition of this invention illustrates the value of the composition of this invention as a foam control agent in the food industry.
  • an air stream is introduced with agitation to produce a foam.
  • the time taken for the foam to rise to the top of the vessel is measured.
  • the air supply is then switched off, agitation stopped, and the time taken for the foam to collapse measured.
  • Composition 6 >300 40
  • Composition 6 retards most effectively foam formation and also provides for an attractive, short, dispersion time of foam should it accumulate.
  • Composition 6 is obtained according to the general procedure of Example 1 by reacting an alkoxylated fatty alcohol represented bythe formula C-oO-(C 2 H4 ⁇ -)gH with 0.94 mole equivalents of isobutyl vinyl ether.
  • the resulting composition contains 6 weight percent alkoxylated fatty alcohol and 94 weight percent of an acetal composition; the acetal composition being constituted by 43.9 weight percent Acetal-1, 50.6 weight percent Acetal-ll and 5.5 weight percent Acetal-lll.
  • Composition 6 exhibits a cloud point temperature of 15°C.
  • Foam control agent DOWFAX DF-1 available from The Dow Chemical Company, is representative of such agents as presently used in the industry for this purpose.
  • compositions of the invention have an enhanced surface activity; exhibit similar or improved cleaning performance; exhibit a highly desirable degree of biodegradability; and exhibit a good degree of foam control.

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Abstract

Composition comprenant un produit d'addition acétal ou cétal d'un polyoxyalkylène à terminaison monohydroxyle. Ces compositions sont utilisées en combinaison avec des procédés de nettoyage et des procédés limitant la formation de mousse, dans des boues de forage, et dans des formulations cosmétiques, pharmaceutiques et pesticides, où il peut être souhaitable de modifier les propriétés tensioactives.
PCT/US1995/007886 1994-06-23 1995-06-21 Composition tensioactive contenant un produit d'addition acetal ou cetal WO1996000253A1 (fr)

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AU28695/95A AU2869595A (en) 1994-06-23 1995-06-21 A surface active composition containing an acetal or ketal adduct

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US26438194A 1994-06-23 1994-06-23
US08/264,381 1994-06-23

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Cited By (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2001041909A1 (fr) * 1999-12-08 2001-06-14 The Procter & Gamble Company Compositions comprenant des agents mouillants a base d'alcools poly(oxyalkyles) coiffes par un ether
WO2001042411A1 (fr) * 1999-12-08 2001-06-14 The Procter & Gamble Company Compositions comprenant des surfactants a alcool poly(oxyalkyle) coiffe d'ether
WO2001041912A3 (fr) * 1999-12-08 2002-02-21 Procter & Gamble Tensioactifs à base d'alcool poly(oxy-alkylé) coiffé d'un éther
US6506945B2 (en) 1999-12-08 2003-01-14 The Procter & Gamble Company Process for preparing ether-capped poly(oxyalkylated) alcohol surfactants
US6593287B1 (en) 1999-12-08 2003-07-15 The Procter & Gamble Company Compositions including ether-capped poly(oxyalkylated) alcohol surfactants
EP1253187A3 (fr) * 2001-04-25 2004-10-06 Kanto Kagaku Kabushiki Kaisha Liquide de lavage pour un analyseur clinique automatise
US6844309B1 (en) 1999-12-08 2005-01-18 The Procter & Gamble Company Ether-capped poly(oxyalkylated) alcohol surfactants
WO2006030184A1 (fr) * 2004-09-14 2006-03-23 Halliburton Energy Services, Inc. Fluides souterrains possedant des caracteristiques ameliorees en matiere d'environnement et procede d'utilisation de ces fluides dans des formations souterraines
WO2009100855A3 (fr) * 2008-02-14 2009-10-08 Cognis Ip Management Gmbh Utilisation de substances tensioactives dans des nettoyants

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FR2204683A1 (en) * 1972-10-25 1974-05-24 Basf Ag Alkali-resistant, low foam surfactant - by reacting polyoxyalkylated alcoh-ol with vinyl alkyl ether in presence of acid catalyst
DE2302876A1 (de) * 1973-01-20 1974-08-01 Basf Ag Alkalistabile, oberflaechenaktive, schaumdaempfende mittel
US3954886A (en) * 1974-11-22 1976-05-04 Basf Wyandotte Corporation Alkali stable polyoxyethylene acetal surfactants
DE3441542A1 (de) * 1984-11-14 1986-05-15 Hoechst Ag, 6230 Frankfurt Grenzflaechenaktive polyglykolaetheracetale
WO1991001171A1 (fr) * 1989-07-12 1991-02-07 Rhone-Poulenc Surfactants And Specialties, L.P. Compositions desemulsifiantes/anti-emulsifiantes a faible viscosite

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GB1164997A (en) * 1965-11-25 1969-09-24 B P Chemicals U K Ltd Improvements in Polyether Polyols and Polyurethanes Derived therefrom
FR2204683A1 (en) * 1972-10-25 1974-05-24 Basf Ag Alkali-resistant, low foam surfactant - by reacting polyoxyalkylated alcoh-ol with vinyl alkyl ether in presence of acid catalyst
DE2302876A1 (de) * 1973-01-20 1974-08-01 Basf Ag Alkalistabile, oberflaechenaktive, schaumdaempfende mittel
US3954886A (en) * 1974-11-22 1976-05-04 Basf Wyandotte Corporation Alkali stable polyoxyethylene acetal surfactants
DE3441542A1 (de) * 1984-11-14 1986-05-15 Hoechst Ag, 6230 Frankfurt Grenzflaechenaktive polyglykolaetheracetale
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Cited By (14)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6844309B1 (en) 1999-12-08 2005-01-18 The Procter & Gamble Company Ether-capped poly(oxyalkylated) alcohol surfactants
WO2001042411A1 (fr) * 1999-12-08 2001-06-14 The Procter & Gamble Company Compositions comprenant des surfactants a alcool poly(oxyalkyle) coiffe d'ether
WO2001041912A3 (fr) * 1999-12-08 2002-02-21 Procter & Gamble Tensioactifs à base d'alcool poly(oxy-alkylé) coiffé d'un éther
US6506945B2 (en) 1999-12-08 2003-01-14 The Procter & Gamble Company Process for preparing ether-capped poly(oxyalkylated) alcohol surfactants
US6593287B1 (en) 1999-12-08 2003-07-15 The Procter & Gamble Company Compositions including ether-capped poly(oxyalkylated) alcohol surfactants
US6686330B2 (en) 1999-12-08 2004-02-03 The Procter & Gamble Company Compositions including ether-capped poly (oxyalkylated) alcohol wetting agents
WO2001041909A1 (fr) * 1999-12-08 2001-06-14 The Procter & Gamble Company Compositions comprenant des agents mouillants a base d'alcools poly(oxyalkyles) coiffes par un ether
EP1253187A3 (fr) * 2001-04-25 2004-10-06 Kanto Kagaku Kabushiki Kaisha Liquide de lavage pour un analyseur clinique automatise
WO2006030184A1 (fr) * 2004-09-14 2006-03-23 Halliburton Energy Services, Inc. Fluides souterrains possedant des caracteristiques ameliorees en matiere d'environnement et procede d'utilisation de ces fluides dans des formations souterraines
US7111684B2 (en) 2004-09-14 2006-09-26 Halliburton Energy Services, Inc. Subterranean fluids having improved environmental characteristics and methods of using these fluids in subterranean formations
US7316742B2 (en) 2004-09-14 2008-01-08 Halliburton Energy Services, Inc. Subterranean fluids having improved environmental characteristics and methods of using these fluids in subterranean formations
WO2009100855A3 (fr) * 2008-02-14 2009-10-08 Cognis Ip Management Gmbh Utilisation de substances tensioactives dans des nettoyants
EP2267110A3 (fr) * 2008-02-14 2011-04-27 Cognis IP Management GmbH Utilisation de substances tensioactives dans des nettoyants
US8148313B2 (en) 2008-02-14 2012-04-03 Cognis Ip Management Gmbh Use of a mixture of non-ionic surfactants in cleansing compositions

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