WO2001076729A2 - Compositions antimousse et utilisations pour de telles compositions - Google Patents

Compositions antimousse et utilisations pour de telles compositions Download PDF

Info

Publication number
WO2001076729A2
WO2001076729A2 PCT/US2001/011142 US0111142W WO0176729A2 WO 2001076729 A2 WO2001076729 A2 WO 2001076729A2 US 0111142 W US0111142 W US 0111142W WO 0176729 A2 WO0176729 A2 WO 0176729A2
Authority
WO
WIPO (PCT)
Prior art keywords
composition
polyetheramine
amine
multifunctional
functional
Prior art date
Application number
PCT/US2001/011142
Other languages
English (en)
Other versions
WO2001076729A3 (fr
Inventor
George A. Smith
Original Assignee
Huntsman Petrochemical Corporation
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 Huntsman Petrochemical Corporation filed Critical Huntsman Petrochemical Corporation
Priority to AU2001253179A priority Critical patent/AU2001253179A1/en
Publication of WO2001076729A2 publication Critical patent/WO2001076729A2/fr
Publication of WO2001076729A3 publication Critical patent/WO2001076729A3/fr

Links

Classifications

    • 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
    • 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
    • B01D19/0413—Foam dispersion or prevention by addition of chemical substances characterised by the nature of the chemical substance compounds containing N-atoms
    • 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
    • C09K23/00—Use of substances as emulsifying, wetting, dispersing, or foam-producing agents
    • 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
    • C09K23/00—Use of substances as emulsifying, wetting, dispersing, or foam-producing agents
    • C09K23/017—Mixtures of compounds
    • 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
    • C09K23/00—Use of substances as emulsifying, wetting, dispersing, or foam-producing agents
    • C09K23/14—Derivatives of phosphoric acid
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
    • C11D3/0005—Other compounding ingredients characterised by their effect
    • C11D3/0026—Low foaming or foam regulating compositions
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
    • C11D3/16—Organic compounds
    • C11D3/37—Polymers
    • C11D3/3703—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • C11D3/3707—Polyethers, e.g. polyalkyleneoxides
    • 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
    • C11D3/37—Polymers
    • C11D3/3703—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • C11D3/3723—Polyamines or polyalkyleneimines

Definitions

  • the present invention relates generally to surfactant compositions, and more particularly to anionic surfactant compositions containing one or more multi-functional polyether amines as foam suppressant s.
  • surfactant is derived from the words "surface active agent”. Within the definition of this word are included various soaps, detergents, emulsifiers, wetting agents, and dispersants. Among other things, surfactants are known for their ability to make water and oil miscible with one another, and this ability is attributed to the property of surfactants in general to form micellular domains owing to the presence of a hydrophobic and hydrophilic portion within the same given surfactant molecule. When surfactants are in a solution, they tend to collect at the surface of the solution, reducing the free energy of the surface, which makes it easier for the solution to spread across a solid. Thus, a further property of surfactants is that they facilitate the wetting of solid surfaces by solutions.
  • hydrophobic and hydrophilic portions within the same molecule may be accomplished in any one of several ways, and since surfactant molecules may be substituted with various alkyl, aryl, inorganic, or other chemical groups or combinations thereof, products available in the marketplace which fall under the classification of surfactant are numerous.
  • foam e.g., soap bubbles
  • foam control is typically achieved by adding a defoamer or anti-foaming agent to the formulation.
  • foam generation is undesirable include, but not limited to, high speed coating operations where foam is detrimental to coating appearance, and in bottle wash and auto dish applications where foam generation tends to decrease cleaning efficiency and causes water spots.
  • One type of conventional defoamer is typically present as a coating on particles of soda ash (sodium carbonate) at, for example, a level of between about 5% to 10%.
  • soda ash sodium carbonate
  • Such materials are free flowing powders, which may be dry blended into various powdered detergent formulations.
  • Examples of such defoaming materials include silicon-based defoamers on inorganic carriers for use with powdered detergents.
  • Drawbacks to these conventional materials include high costs and potential wetting and leveling problems in coating applications.
  • surfactant compositions including multifunctional polyether amines which are effective as defoamers in laundry detergent formulations that include anionic surfactants.
  • the disclosed multifunctional polyether amine foam suppressants may be employed with both powder and liquid laundry detergent formulations, and are effective regardless of water hardness, thus providing an attractive alternative to soap defoamers which are typically employed with liquid laundry detergents.
  • the disclosed multifunctional polyether amine foam suppressants may be employed to suppress or eliminate foam in a variety of aqueous surfactant systems containing anionic surfactants.
  • aqueous surfactant systems known in the art such as low foam laundry detergents (including high efficiency laundry formulations), bottle wash formulations, auto dish formulations, high speed coating operation formulations, etc.
  • the disclosed multifunctional polyether amine foam suppressants may be employed in solid surfactant compositions (e.g., powdered laundry detergents), absorbing a multifunctional polyether amine on a solid carrier, such as magnesium silicate.
  • the disclosed foam suppressants may offer additional advantages, such as the ability to formulate a 100% active liquid composition that requires no water and therefore offers savings in weight, space and cost associated with transportation.
  • the disclosed foam suppressants may offer anti- redeposition properties and/or act to stabilize and disperse soil particles.
  • the disclose foam suppressants may provide dye transfer inhibition properties which may prevent bleeding or transfer of colored dyes from one laundry item to another. The foregoing is only a partial list of possible benefits and advantages that may be offered by the disclosed foam suppressant compositions.
  • the disclosed foam suppressants may be employed in surfactant systems (such as laundry formulations) that have an alkaline pH, for example, a pH of from about 7 to about 9 for enzymatic formulations, and a pH of from about 8 to about 12, alternatively from about 8 to about 11, further alternatively of about 10, for non-enzymatic built liquids.
  • surfactant systems such as laundry formulations
  • an alkaline pH for example, a pH of from about 7 to about 9 for enzymatic formulations, and a pH of from about 8 to about 12, alternatively from about 8 to about 11, further alternatively of about 10, for non-enzymatic built liquids.
  • these pH ranges are exemplary only, and that the disclosed foam suppressants may be employed with surfactant compositions having pH values outside these ranges as well.
  • foam suppressants may be formulated from polyether amines that do not contain alkyl groups synthesized from alcohols.
  • polyether amine molecules may remain substantially unassociated in solution, i.e., they form substantially no micelles in solution. This feature tends to allow the formulation of more effective foam suppressants at lower use concentrations.
  • compositions including: at least one anionic surfactant; and at least one multifunctional polyetheramine including at least two amine groups per molecule, and having a molecular weight of at least about 1000; wherein each of the amine groups is a secondary amine group, or a tertiary amine group; and wherein none of the substituent groups attached to a nitrogen atom of the multifunctional polyetheramine is an n- propyl group or radical, or an alkyl group or radical having more than four carbon atoms.
  • liquid surfactant composition including: at least one anionic surfactant; at least one multifunctional polyetheramine, the multifunctional polyetheramine including two or three amine groups per molecule, and having a molecular weight of from about 1000 to about 10,000; and solvent; wherein the multifunctional polyetheramine is present in the composition in an amount effective to suppress foam in the composition when the composition is combined with water; and wherein the multifunctional polyetheramine includes a di-functional amine of the formula:
  • x may be from about 25 to about 100;
  • R may be one of H, (CH 2 CH 2 O) n ⁇ -H, or (CH 2 CH(CH 3 )0) n i-H;
  • R 2 may be one of H, (CH 2 CH 2 O) n2 -H, or (CH 2 CH(CH 3 )0) ⁇ 2 -H;
  • R 3 may be one of H, (CH 2 CH 2 O) n3 -H, or (CH 2 CH(CH 3 )0) discourse 3 -H;
  • R4 may be one of H, (CH 2 CH 2 O) thread 4 -H, or (CH 2 CH(CH 3 )O) n4 -H;
  • nl, n2, n3, and n4 may be independently from about 1 to 20; or
  • multifunctional polyetheramine includes a di-functional amine of the formula:
  • b may be from about 5 to about 50, and a+c may be from about 2 to about 20;
  • Ri may be one of H, (CH 2 CH 2 0) n ⁇ -H, or (CH 2 CH(CH 3 )O) n ⁇ -H;
  • R 2 may be one of H, (CH 2 CH 2 0) n2 -H, or (CH 2 CH(CH 3 )O) n2 -H;
  • R 3 may be one of H, (CH 2 CH 2 O) n3 -H, or (CH 2 CH(CH 3 )O) n3 -H;
  • R4 may be one of H, (CH 2 CH 2 0) n -H, or (CH 2 CH(CH 3 )0) n4 -H;
  • nl, n2, n3 and n4 may be independently from about 1 to
  • multifunctional polyetheramine includes a tri-functional amine of the formula:
  • x+y+z may be from about 5 to about 100;
  • Ri may be one of H, (CH 2 CH 2 0) n *-H, or (CH 2 CH(CH 3 )0) n i-H;
  • R 2 may be one of H, (CH 2 CH 2 0) n2 -H, or (CH 2 CH(CH 3 )O) n2 -H;
  • R 3 may be one of H, (CH 2 CH 2 0) n3 -H, or (CH 2 CH(CH 3 )O) n3 -H;
  • R4 may be one of H, (CH 2 CH 2 0) n4 -H, or (CH 2 CH(CH 3 )O) n4 -H;
  • R 5 may be one of H, (CH 2 CH 2 O) n5 -H, or (CH 2 CH(CH 3 )O) n5 -H;
  • Re may be one of H, (CH 2 CH 2 0) n6 -H, or (CH 2 CH(CH 3 )0) n6 -H;
  • nl, n2, n3, n4, n5 and n6 may be independently from about 1 to 20; or
  • multifunctional polyetheramine includes a tri-functional amine of the formula:
  • x+y+z equals from about 3 to about 100;
  • a+b+c equals from about 3 to about 30;
  • R may be one of H, (CH 2 CH 2 O) n ⁇ -H, or (CH 2 CH(CH 3 )0) n] -H;
  • R 2 may be one of H, (CH 2 CH 2 O) n2 -H, or (CH 2 CH(CH 3 )O) n2 -H;
  • R 3 may be one of H, (CH 2 CH 2 O) n3 -H, or (CH 2 CH(CH 3 )O) n3 -H;
  • R> may be one of H, (CH 2 CH 2 0) n4 -H, or (CH 2 CH(CH 3 )0) n -H;
  • R 5 may be one of H, (CH 2 CH 2 O) n5 -H, or (CH 2 CH(CH 3 )0) n5 -H;
  • Re may be one of H, (CH 2 CH 2 O) n6 -H, or (CH 2 CH(CH 3 )0) n6 -H;
  • nl, n2, n3, n4, n5 and n6 may be independently from about 1 to 20; or a mixture thereof.
  • a composition including at least one multi-functional polyetheramine adsorbed onto the surface of particles of solid carrier; the multi-functional polyetheramine having a molecular weight of at least about 1000.
  • a method of suppressing foam in an aqueous surfactant system including combining a multi-functional polyetheramine with the aqueous surfactant solution; wherein the aqueous surfactant system includes at least one anionic surfactant; wherein the multi-functional polyetheramine includes at least two amine groups per molecule, and has a molecular weight of at least about 1000; wherein each of the amine groups is a primary amine group, a secondary amine group, or a tertiary amine group; wherein each tertiary amine group present includes a nitrogen atom bound to three adjacent substituent groups, each of the adjacent substituent groups being (CH 2 CH 2 O)-H or (CH 2 CH(CH 3 )O)-H; and wherein the multi-functional polyetheramine is present in an amount to suppress foam in the surfactant solution when the solution is combined with water.
  • FIG. 1 shows foam height as a function of concentration of multifunctional polyether amine in a surfactant composition according to one embodiment of the disclosed compositions and methods.
  • FIG. 2 shows foam height comparison for surfactant compositions containing a variety of polyether amines
  • FIG. 3 shows foam height as a function of concentration of multifunctional polyether amines in a surfactant composition according to two embodiments of the disclosed compositions and methods.
  • multifunctional polyether amines may be added to or otherwise combined with a surfactant systems including at least one anionic surfactant.
  • Suitable multifunctional polyether amines include any polyether amine having at least two amine groups per molecule, and having a molecular weight sufficiently high enough to reduce or eliminate foam formation, for example, as compared to the same surfactant solution absent one or more of the disclosed multifunctional polyether amines. W ile not wishing to be bound by theory, it is believed that amine groups of multifunctional polyether amines are capable of neutralizing charged head groups in an anionic surfactant, forming a salt and effectively coupling the anionic surfactant to the polyether amine molecule.
  • a difimctional polyether amine in this embodiment, a "JEFF AMINE ED®” compound having two primary amine groups, available from Huntsman Corporation, and described further herein
  • a linear alkyl benzene sulfonate is illustrated below.
  • Example 2 Among the variables which may affect the foam suppression effectiveness of a multifunctional polyether amine are molecular weight, hydroprobicity and functionality. As illustrated in Example 2, favorable foam suppression characteristics may be achieved using multifunctional species, suggesting that two or more anionic surfactant molecules are bound by multifunctional polyether amines to suppress the foam. Furthermore, the data from Example 2 also suggests that foam suppression characteristics tend to increase with increasing molecular weight and increasing hydroprobicity of a multifunctional polyether amine molecule. This suggests that the polyether amine surfactant complex may form small hydrophobic particles at the air/water interface which serve to suppress the foam.
  • Suitable multifunctional polyether amines include polyether amines having two or more amine groups per molecule. Suitable amine groups include primary, secondary and tertiary amine groups, as well as mixtures thereof. Specific examples of suitable polyether amines include, but are not limited to, difimctional and trifunctional polyether amines having two or three primary amine groups per molecule, respectively. Suitable multifunctional polyether amines may have polyether blocks comprised of alkylene oxide-based groups, wherein each group has a carbon count of from about 2 to about 5. The multifunctional polyether amines may be comprised of individual polyether blocks having the same number of carbon atoms and structure, or alternatively may be composed of individual polyether groups having differing carbon counts and/or isomeric structure.
  • Suitable polyether blocks for polyetheramine include, for example, polyethylene glycol, polypropylene glycol, copolymers of polyethylene glycol and polypropylene glycol, poly (1,2-butylene glycol), and poly (tetramethylene glycol).
  • Glycols may be aminated using well-known methods to produce the polyetheramines.
  • glycols may be prepared from ethylene oxide, propylene oxide or combinations thereof using methods such as methoxy or hydroxy initiated reaction. When both ethylene oxide and propylene oxide are used, the oxides can be reacted simultaneously when a random polyether is desired, or reacted sequentially when a block polyether is desired.
  • polyetheramines may be prepared from ethylene oxide, propylene oxide or combinations thereof.
  • the amount of ethylene oxide on a molar basis may range from about 0 to about 100% of the polyetheramine.
  • Polyols and amines, including polyalkylene polyamines and alkanol amines or any amine that is not a polyetheramine as disclosed herein, may be absent from the composition.
  • functional groups other than ether linkages and amine groups may be absent from a polyetheramine.
  • Suitable polyetheramines may be prepared, for example, using amination techniques such as described in United States Patent Nos. 3,654,370; 4,152,353; 4,618,717; 4,766,245; 4,960,942; 4,973,761; 5,003,107; 5,352,835; 5,422,042; and 5,457,147, each of which is incorporated herein by reference.
  • polyetheramines may be made by aminating a polyol, such as a polyether polyol with ammonia in the presence of a catalyst such as a nickel-containing catalyst (e.g., Ni/Cu/Cr catalyst, etc.).
  • multifunctional polyether amine foam suppressants include those polyether amines having two or more amines per molecule, and having a molecular weight sufficiently high to be effective to suppress foam formation in a surfactant composition when present in an effective amount.
  • such multifunctional polyether amines may have a molecular weight of at least about 1000, alternatively of at least about 1500, and alternatively of at least about 2000.
  • suitable multifunctional polyether amines include, but are not limited to, diamines and triamines having a molecular weight of from about 1000 to about 10,000, alternatively from about 1500 to about 10,000, alternatively from about 2000 to about 10,000, alternatively from about 1000 to about 7500, alternatively from about 1500 to about 7500, alternatively from about 2000 to about 7500, alternatively from about 1000 to about 5000, alternatively from about 1500 to about 5000, alternatively from about 2000 to about 5000, alternatively from about 1000 to about 4000, alternatively from about 1500 to about 4000, alternatively from about 2000 to about 4000.
  • multifunctional polyether amines having a molecular weight in a range of from about A to about B may be employed, where for each respective embodiment the value of A may be selected from the range of whole number values of from about 1000 to about 2000, and a corresponding value of B may be selected from the range of whole number values of from about 5000 to about 10,000.
  • a multifunctional polyether amine having a molecular weight of from about 1050 to about 6500 would be represented.
  • multifunctional polyether amines having a molecular weight in a range of greater than about A may be employed, where the value of A may be selected from the range of whole number values of from about 1000 to about 2000.
  • each of said amine groups of a multifunctional polyetheramine is a primary amine group, a secondary amine group, or a tertiary amine group; with the provision that each tertiary amine group present comprises a nitrogen atom bound to three adjacent substituent groups that are each (CH 2 CH 2 0)-H or (CH 2 CH(CH 3 )0)- H.
  • these materials may be used in their nonionic form at pH values above the pKa, or in their cationic form at pH values below their pKa.
  • none of the substituent groups attached to a nitrogen atom of a multifunctional polyetheramine is an w-propyl group (or radical), or an alkyl group (or radical) having more than four carbon atoms.
  • suitable difimctional polyether amines include, but are not limited to, "JEFFAMINE D®” di-functional difimctional amines, available from Huntsman Corporation (including alkoxylated derivatives thereof), and having the following structure (“Structure A”):
  • Ri is one of H, (CH 2 CH 2 O) n ⁇ -H, or (CH 2 CH(CH 3 )O) expect ⁇ -H;
  • R 2 is one of H, (CH 2 CH 2 0) n2 -H, or (CH 2 CH(CH 3 )0) n2 -H;
  • R 3 is one of H, (CH 2 CH 2 0) n3 -H, or (CH 2 CH(CH 3 )O) n3 -H;
  • R4 is one of H, (CH 2 CH 2 0) prison 4 -H, or (CH 2 CH(CH 3 )O) n4 -H;
  • each of nl, n2, n3 and n4 may be independently from about 1 to 20;
  • difunctional amines include, but are not limited to, Jeffamine® D-2000 and D-4000, and mixtures thereof.
  • x is about 33 and each of Ri, R 2 , R 3 , and R is H.
  • x is about 68 and each of Ri, R 2 , R 3 , and Rt is H.
  • ethoxylated and propoxylated versions of these exemplary difunctional amines are also suitable, as are mixtures thereof.
  • JEFFAMINE® polyetheramines
  • a numeric suffix is provided that indicates the weight average molecular weight.
  • An alphabetic designation precedes each numeric suffix, identifying the functionality of the particular compound: "M” for monofunctional, “D” for difunctional, and “T” for trifunctional.
  • the letter “E” (such as in "JEFFAMINE® ED-2000") denotes a predominantly polyethylene oxide backbone.
  • an additional alphanumeric subscript is provided that indicates moles of alkoxylation, and identity of alkoxy group, respectively.
  • JEFFAMINE® D-2000-4EO and "JEFFAMINE® D-4000- 4EO” denote Jeffamine® D-2000 and Jeffamine® D-4000 amine molecules, respectively (as described above), having 4 moles of ethoxylation (i.e., in Structure A each of Rj, R 2 , R , and R 4 is (CH 2 CH 2 O)-H; and each of nl, n2, n3 and n4 has a value of one).
  • suitable difunctional polyether amines (and alkoxylated derivatives thereof) having Structure A may have a value of x that is from about 16 to about 100, with the remaining variables being the same as given above (i.e., values of "R" and "n”).
  • difunctional polyether amines (and alkoxylated derivatives thereof) having Structure A, and having a value of x in a range of from about C to about D may be employed, where for each respective embodiment the value of C may be selected from the range of whole number values of from about 16 to about 99, and a corresponding value of D may be selected from the range of whole number values of from about 17 to about 100. It will be understood with benefit of this disclosure by those of skill in the art that value of x be varied to obtain desired molecular weight values and minimum molecular weight values to fit particular requirements and/or applications.
  • Ri, R 2 , R 3 , and/or R 4 represent one or more alkoxyl groups
  • the corresponding value (or minimum value) of x may be adjusted downward accordingly to achieve a given molecular weight (or minimum molecular weight).
  • Suitable difunctional polyetheramines include, but are not limited to, "JEFFAMINE ED®” compounds, available from Huntsman Corporation, and having the following structure (“Structure B”): R l R 3
  • b is from about 5 to about 50, and a+c is from about 2 to about 20;
  • Ri is one of H, (CH 2 CH 2 0) complicat--H, or (CH 2 CH(CH 3 )0) n i-H;
  • R 2 is one of H, (CH 2 CH 2 O) ⁇ 2 -H, or (CH 2 CH(CH 3 )O) n2 -H;
  • R 3 is one of H, (CH 2 CH 2 O) n3 -H, or (CH 2 CH(CH 3 )O) n3 -H;
  • RA is one of H, (CH 2 CH 2 O) n4 -H, or (CH 2 CH(CH 3 )O) n -H;
  • each of nl, n2, n3 and n4 may be independently from about 1 to 20;
  • these difunctional polyetheramines include, but are not limited to, Jeffamine® ED-2003.
  • b is about 38.7, a+c is about 6, and each of Ri, R 2 , R , and R 4 is H.
  • b is about 86.0, a+c is about 2.5, and each of R-, R 2 , R 3 , and R 4 is H.
  • b is about 132, a+c is about 3.0, and each of Ri, R 2 , R , and Ri is H.
  • ethoxylated and propoxylated versions of these exemplary difunctional polyetheramines are also suitable, as are mixtures thereof.
  • suitable difunctional polyether amines (and alkoxylated derivatives thereof) having Structure B may have a value of b that is from about 1 to about 50, and a value of a+c that is from about 2 to about 20, with the remaining variables being the same as given above (i.e., values of "R" and "n").
  • difunctional polyether amines (and alkoxylated derivatives thereof) having Structure B and having a value of b in a range of from about C to about D, and a value of a+c in a range of from about E to F, may be employed, where for each respective embodiment the value of C may be selected from the range of whole number values of from about 1 to about 49, and a corresponding value of D may be selected from the range of whole number values of from about 2 to about 50; and a value of E may be selected from the range of whole number values of from about 2 to about 19, and a corresponding value of F may be selected from the range of whole number values of from about 3 to about 20. It will be understood with benefit of this disclosure by those of skill in the art that values of b and a+c may be varied to obtain desired molecular weight values and minimum molecular weight values to fit particular requirements and/or applications.
  • values of a, b and c may be selectively and independently varied to achieve desired molecular weight and/or foam suppressant properties.
  • the value of b may be from about 1 to about 50, and the corresponding value of a+c from about 15 to about 20.
  • the value of b may be from about 18 to about 50.
  • Ri, R 2 , R 3 , and/or R represent one or more alkoxyl groups
  • the corresponding values (or minimum values) of b and/or a+c may be adjusted downward accordingly to achieve a given molecular weight (or minimum molecular weight).
  • Suitable trifunctional polyether amines include, but are not limited to, "JEFFAMINE® T” compounds, available from Huntsman Corporation, and having the following structure (“Structure C”):
  • x+y+z is from about 5 to about 100;
  • Ri is one of H, (CH 2 CH 2 0) n ⁇ -H, or (CH 2 CH(CH 3 )0) n i-H
  • R 2 is one of H, (CH 2 CH 2 0) n2 -H, or (CH 2 CH(CH 3 )0) n2 -H
  • R 3 is one of H, (CH 2 CH 2 O) n3 -H, or (CH 2 CH(CH 3 )O)trust 3 -H
  • R 4 is one of H, (CH 2 CH 2 0) n4 -H, or (CH 2 CH(CH 3 )0) n -H:
  • R 5 is one of H, (CH 2 CH 2 0) n5 -H, or (CH 2 CH(CH 3 )0) n5 -H:
  • Re is one of H, (CH 2 CH 2 O) n e-H, or (CH 2 CH(CH 3 )0)cosm 6 -H
  • each of nl, n2, n3, n4, n5 and n6 may be independently from about 1 to 20;
  • ethoxylated and propoxylated versions of these exemplary difunctional polyetheramines are also suitable, as are mixtures thereof.
  • JEFFAMINE® T-5000-6EO denotes an alkoxylated Jeffamine® T-5000 amine molecule (as described above), having 6 moles of ethoxylation (i.e., in Structure C each of Ri, R 2 , R , R4, R 5 , and Re is (CH 2 CH 2 O)-H; and each of nl, n2, n3, n4, n5 and n6 has a value of one).
  • suitable trifunctional polyether amines (and alkoxylated derivatives thereof) having Structure C may have a value of x+y+z that is from about 13 to about 100, with the remaining variables being the same as given above (i.e., values of "R" and "n”).
  • difunctional polyether amines (and alkoxylated derivatives thereof) having Structure C, and having a value of x+y+z in a range of from about C to about D may be employed, where for each respective embodiment the value of C may be selected from the range of whole number values of from about 13 to about 99, and a corresponding value of D may be selected from the range of whole number values of from about 14 to about 100. It will be understood with benefit of this disclosure by those of skill in the art that values of x+y+z may be varied to obtain desired molecular weight values and minimum molecular weight values to fit particular requirements and/or applications.
  • Ri, R 2 , R 3 , R 4 , R 5 , and R 6 represent one or more alkoxyl groups
  • the corresponding values (or minimum values) of x+y+z may be adjusted downward accordingly to achieve a given molecular weight (or minimum molecular weight).
  • Suitable trifunctional polyether amines include, but are not limited to, compounds such as "JEFFAMINE® ET” compounds, formerly available from Huntsman Corporation, and having the following structure (“Structure D”): CH, CH,
  • x+y+z equals from about 3 to about 100;
  • a+b+c equals from about 3 to about 30;
  • R is one of H, (CH 2 CH 2 0) n ⁇ -H, or (CH 2 CH(CH 3 )O) n ⁇ -H;
  • R 2 is one of H, (CH 2 CH 2 0) n2 -H, or (CH 2 CH(CH 3 )0) n2 -H;
  • R 3 is one of H, (CH 2 CH 2 0) n3 -H, or (CH 2 CH(CH 3 )0) n3 -H;
  • R 4 is one of H, (CH 2 CH 2 0) n -H, or (CH 2 CH(CH 3 )O) n -H;
  • R 5 is one of H, (CH 2 CH 2 0) n5 -H, or (CH 2 CH(CH 3 )O)trust 5 -H;
  • Re is one of H, (CH 2 CH 2 0) n6 -H, or (CH 2 CH(CH 3 )O) n6 -H;
  • each of nl, n2, n3, n4, n5 and n6 may be independently from about 1 to 20;
  • difunctional polyether amines are provided.
  • x, y and z; and/or a, b and c may be selectively and independently varied to achieve desired molecular weight and/or foam suppressant properties.
  • a molecular weight of at least about 1000 when each of Ri, R 2 , R 3 , R t , R 5 , and Re are H then the value of a+b+c may be from about 3 to about 100, and the corresponding value of x+y+z may be from about 13 to about 20.
  • a+b+c when the value of a+b+c is from about 10 to about 100, then the corresponding value of x+y+z may be from about 3 to about 20.
  • Ri, R 2 , R 3 , t, R 5 , and Re represent one or more alkoxyl groups, the corresponding values (or minimum values) of b and/or a+c may be adjusted downward accordingly to achieve a given molecular weight (or minimum molecular weight).
  • Suitable multifunctional amines include, but are not limited to, "POLYETHERAMINE D2000,” available from BASF; and ethoxylated or propoxylated versions thereof.
  • foam suppression benefits of the disclosed polyetheramine/anionic surfactant systems may be realized with the presence of even small amounts of a suitable polyetheramine in an aqueous liquid surfactant solution. In one embodiment, amounts as little as about 0.1% may be employed.
  • polyetheramine is employed in an amount of at least about 0.5% alternatively from about 0.5% to about 10%, alternatively from about 1% to about 10%, and further alternatively from about 1% to about 5% by weight of solution alternatively from about 1% to about 8%, alternatively from about 1% to about 7%, alternatively from about 1% to about 6%, alternatively from about 1% to about 5%, alternatively from about 1% to about 4%, alternatively from about 1% to about 3%, alternatively from about 1% to about 2%, and further alternatively from about 2% to about 10%, alternatively from about 2% to about 9%, alternatively from about 2% to about 8%, alternatively from about 2% to about 7%, alternatively from about 2% to about 6%, alternatively from about 2% to about 5%, alternatively from about 2% to about 4%, alternatively from about 2% to about 3%, alternatively from about 2% to about 2%.
  • a surfactant composition may be formulated using components described elsewhere herein so that substantially equivalent molar amounts of amine functionality and surfactant acid functionality are present, so that substantially all of the acid functionality is neutralized.
  • anionic surfactants that may be employed in the disclosed compositions and methods include any anionic surfactant known in the art and suitable for detergent or coating applications.
  • anionic surfactants may be characterized as having pKa values less than 7.
  • suitable anionic surfactants include, but are not limited to, linear and/or branched chain alkylbenzene sulfonates, alkyl sulfates, ether sulfates, xylene sulfonates, alcohol sulfates, phosphate esters, napthalene sulfonates, secondary alkyl sulfates, ⁇ -oleftn sulfonates, phosphate esters, sulfosuccinates, isethionates, carboxylates, betaines, soaps, mixtures thereof, etc.
  • Most of these surfactants are typically sold in the form of a sodium salt, although forms having other cations may be employed, as described below.
  • an anionic surfactant such as alkylbenzene sulfonate
  • a counterion or cation may be ammonium or substituted ammonium compounds.
  • a substituted ammonium may include, but is not limited to, monoethanol ammonium, diethanol ammonium, triethanol ammonium, or a mixture thereof.
  • such a counterion or cation may be an alkali metal, an alkaline earth metal, or a mixture thereof.
  • alkali metals include, but are not limited to, lithium, sodium, potassium, cesium, or a mixture thereof.
  • alkaline earth metals include, but are not limited to, magnesium, calcium, strontium, barium, or a mixture thereof.
  • alkylbenzene sulfonate/s may be employed as anionic surfactants.
  • alkylbenzene sulfonate compounds having varying molecular weights, alkyl chain length and alkyl chain phenyl location combination may be employed. Examples of such compounds may be found in U.S. Patent No. 3,776,962; U.S. Patent No. 5,152,933; U.S. Patent No. 5,167,872; Drazd, Joseph C.
  • Linear alkylbenzene sulfonates are one type of alkylbenzene sulfonate widely used as surfactants in commercial cleanser products because of their effectiveness as detergents, ease of biodegradation, and relative low cost. Linear alkylbenzene sulfonates may be produced via sulfonation of linear alkylbenzene intermediates.
  • Linear alkylbenzene is typically manufactured on an industrial scale using one of two commercial processes which differ from one another primarily by virtue of the catalyst system employed.
  • one process employs an aluminum trichloride catalyst, while the other process uses a hydrogen fluoride catalyst.
  • the two processes result in linear alkylbenzene products with different phenyl isomer distributions.
  • a typical phenyl isomer distribution for products of the aluminum trichloride process is about 30% 2-phenyl isomer and about 22% 3- phenyl isomer.
  • a typical phenyl isomer distribution for products of the hydrogen fluoride process is about 20% 2-phenyl isomer and about 20% 3-phenyl isomer, although reported values may differ.
  • alkylbenzene sulfonate compounds used in accordance with the disclosed compositions and methods and having the characteristics described herein include those having a linear alkyl group.
  • linear alkyl chain lengths are between about 8 and about 16 carbon atoms, although greater and lesser lengths are also possible.
  • One specific low 2-phenyl alkylbenzene sulfonate composition is a sulfonate prepared from a linear alkyl benzene known as "ALKYLATE 225TM” (commercially available from Huntsman Specialty Chemicals Corporation).
  • suitable linear alkylbenzenes for preparing linear alkyl benzene sulfonates include, but are not limited to, "ALKYLATE 215TM”, “ALKYLATE 229TM”, “ALKYLATE H230LTM”, “ALKYLATE H230HTM", and mixtures thereof (also available from Huntsman Specialty Chemicals Corporation).
  • Suitable processes for sulfonating such linear alkyl benzenes include, but are not limited to, those employing an air/S0 3 sulfonator or chlorosulfonic acid.
  • anionic surfactants include, but are not limited to, the surfactants listed in Table 1 and available from Huntsman Corporation, Houston, Texas. Table 1
  • anionic surfactants include, but are not limited to, the surfactants listed in Table 2 available from Witco Corporation, Greenwich, CT.
  • anionic surfactants include, but are not limited to, the surfactants listed in Table 3 and available from Stepan Company. Table 3
  • anionic surfactants are exemplary only, and that other anionic surfactants meeting criteria set forth herein may also be employed.
  • an amount of anionic surfactant employed in the disclosed surfactant compositions may include any amount of anionic surfactant known in the art to be suitable for formulating a surfactant composition, such as a liquid detergent composition, solid surfactant composition, or coating composition
  • an aqueous liquid surfactant composition may comprise from about 1% to about 30% alternatively from about 5% to about 15% by weight of total weight of the composition of one or more anionic surfactant/s, although greater or lesser amounts are also possible.
  • the disclosed surfactant compositions may be provided in solid form without a solvent (such as adsorbed on magnesium silicate and/or as a solid which may be combined with a solvent later), or in liquid form with a solvent.
  • any solvent suitable for use in the formulation of a liquid detergent formulation may be employed.
  • suitable solvents include, for example, those solvents capable of dissolving anionic surfactants such as those described elsewhere herein. Examples of suitable solvents include, but are not limited to, water, alcohols, glycols and glycol ethers, cyclic carbonates, pine oil, methyl esters, limonene, aliphatic and aromatic hydrocarbons, or mixtures thereof.
  • suitable alcohol solvents include, but are not limited to, alcohols having from about 1 to about 6 carbon atoms.
  • typical specific solvents include water, straight chain alkyl alcohols containing from one to six carbon atoms (examples: methanol, ethanol, n-propanol, n-hexanol.
  • branched chain alkyl alcohols containing from three to six carbon atoms examples: isopropanol and secondary butanol
  • glycols such as propylene glycol, diglycols such as propylene diglycol and triglycols such as triethylene glycol and glycol ethers such as butylene glycol diethylether and dipropylene glycol methylether.
  • embodiments of the disclosed surfactant compositions include anionic surfactants/s blended or combined with one or more multi-functional polyetheramines.
  • anionic surfactants/s blended or combined with one or more multi-functional polyetheramines include anionic surfactants/s blended or combined with one or more multi-functional polyetheramines.
  • other optional ingredients may also be added if so desired.
  • one or more nonionic surfactants may also be added, for example, to lower mixture viscosity without destroying the salt, and/or in an amount sufficient to dissolve the anionic-polyetheramine, although greater or lesser amounts are also possible.
  • any nonionic surfactant or mixture thereof suitable for lowering the pour point may be employed.
  • nonionic surfactants include, but are not limited to, nonylphenol ethoxylates, alcohol ethoxylates, ethylene oxide/propylene oxide (“EO-PO") block copolymers, alcohol ethylene oxide/propylene oxide adducts, and mixtures thereof.
  • EO-PO ethylene oxide/propylene oxide
  • Specific examples include, but are not limited to, nonylphenol ethoxylates such as "SURFONIC® N- 95 available from Huntsman and linear alcohol ethoxylates such as "SURFONIC® L-24-7" also available from Huntsman.
  • Other examples include, but are not limited to, nonionic surfactants commercially available from Huntsman Corporation and Witco, as described below.
  • nonionic surfactants available from Huntsman Corporation include, but are not limited to, surfactants listed in Table 4.
  • nonionic surfactants available from Witco include but are not limited to, surfactants listed in Table 5.
  • nonionic surfactants available from Stepan include, but are not limited to, surfactants listed in Table 6.
  • neutralization of anionic surfactants in the disclosed surfactant compositions may be accomplished with the addition of a basic compound.
  • optional neutralizing compounds include, but are not limited to, alkanolamines, alkyl amines, NFL-.OH, NaOH, KOH, and mixtures thereof.
  • Amounts of neutralizing compound may be any amount suitable for partially or completely neutralizing an anionic surfactant acid. In one embodiment, an amount of neutralizing compound sufficient to neutralize about 75% of the anionic surfactant is employed, although greater or lesser amounts are also possible.
  • Sufficient polyetheramine may be employed in conjunction with the neutralization compound to neutralize about 25% of the anionic surfactant.
  • additives may be employed, including materials know to those of skill in the art in the formulation of surfactant and/or detergent compositions. Examples include, but are not limited to, optical brighteners, anti-redeposition polymers, dye transfer inhibitors, preservatives, enzymes, builders, chelating agents, etc.
  • the disclosed multi-functional polyetheramine compositions may also be adsorbed onto solid carriers, alone or in combination with anionic and/or other surfactants.
  • a solid carrier is defined as any substantially free flowing solid material suitable for detergent or coating applications.
  • suitable solid carriers include, but are not limited to, magnesium silicate particles, soda, ash, salt, clay, pigments, etc., mixtures thereof, etc.
  • types and uses of such solid carriers with surfactants and defoamers may be found in United States Patent Application Serial No. 09/303,096 filed April 29, 1999, and entitled “Adsorbed Surfactants and Uses Therefor", which is inco ⁇ orated herein by reference.
  • multi-functional polyetheramine defoaming or anti-foaming compounds may be adsorbed, alone or in combination with surfactants, onto amorphous precipitated metallic silicate materials described elsewhere herein.
  • amorphous magnesium silicate solid carrier materials may comprise compositions of the formula M y O: X Si0 2 , in which X is between 2.00 and 3.00 including every hundredth therebetween, and wherein M is a metal atom selected from the group consisting of a mono or divalent metal atom, and is most preferably an alkali metal or alkaline earth metal.
  • M is a monovalent metal atom
  • the value of y may be 2.
  • the value of y may be 1.
  • magnesium silicate solid carrier materials include, but are not limited to, a family of compounds known as "MAGNESOL®” which are available from The Dallas Group of America, Inc. 1402 Fabricon Blvd., Jeffersonville, Indiana. These compounds are a synthetic amorphous hydrous form of magnesium silicate which are pure white, odorless, and tasteless having the approximate chemical formula MgO : 2.6SiO 2 .
  • the materials have a porous internal structure and a large activated surface area. Two such materials are known as "MAGNESOL® Super Flow” and "MAGNESOL® Flow Plus.”
  • loadings of about 1:1 on a weight basis of polyetheramine anti-foaming agent (defoamer) to magnesium silicate are possible, while still producing a material which is free-flowing.
  • Exemplary weight ratios of multi-functional polyetheramine to magnesium silicate include, but are not limited to, from about 1% to about 150%, alternatively from about 50% to about 100% by weight percent. However, greater and lesser weight percentage values are also possible.
  • multi-functional polyetheramine may be present in an amount of between about 1 weight % to about 75 weight % based on total weight of the composition, surfactant may be present in an amount of between about 1 weight % to about 75 weight % based on total weight of the composition, and magnesium silicate may be present in an amount of between about 25 weight % to about 99 weight % based on total weight of the composition.
  • multi-functional polyetheramine may be present in an amount of between about 1 weight % to about 50 weight % based on total weight of the composition
  • surfactant may be present in an amount of between about 1 weight % to about 50 weight % based on total weight of the composition
  • magnesium silicate may be present in an amount of between about 50 weight % to about 99 weight % based on total weight of the composition.
  • weight percentages are exemplary only, and that the weight percentage of any given component may be greater or lesser than the values given in the ranges above.
  • magnesium silicate is useful as an anti-caking agent and possesses whiteness-improving characteristics when used in laundry detergents
  • precipitated magnesium silicate particles having an adsorbed polyetheramine antifoaming agent are capable of simultaneously functioning as an anti-foaming agent, anti-caking additive, and/or as a whitening agent, thus making preparation and use of detergents containing such materials more convenient and economical in comparison to conventional methods known in the art.
  • consistency of manufactured quality from batch to batch of detergent using such materials may be greatly increased.
  • Production of solid carrier materials having surfactants and/or multi-functional polyethermines adsorbed thereon may be carried out in any manner of contacting or combining of solid carrier material with selected surfactants and/or polyetheramines suitable to achieve adsorption of one or more of these compounds onto the solid carrier.
  • one method my be carried out by first providing the material to be adsorbed (e.g., surfactant and/or polyetheramine), and by next causing the solid carrier (e.g., MAGNESOL®) to come into contact with the material to be adsorbed for a time period sufficient for adsorption.
  • the material to be adsorbed e.g., surfactant and/or polyetheramine
  • the solid carrier e.g., MAGNESOL®
  • solid carrier materials having adsorbed multi-functional polyetheramines may be employed as anti-foaming agents or defoamers by combining them in aqueous solution with one or more surfactants, such as one or more of the anionic surfactants described herein.
  • surfactants such as one or more of the anionic surfactants described herein.
  • both multi-functional polyetheramine and anionic surfactant components may be adsorbed onto a solid carrier material that may be combined with an aqueous solution to form a liquid surfactant solution.
  • solid carrier materials having adsorbed multi-functional polyetheramine and surfactant components (i.e., anionic, nonionic, and/or canonic surfactants), which may then be combined in solution with other surfactant/s of any given type.
  • surfactant components i.e., anionic, nonionic, and/or canonic surfactants
  • Examples of uses for the disclosed multi-functional polyetheramine defoaming agents include, but are not limited to, wet or dry formulations for agricultural use (including, but not limited to, those employed as soil penetrants, defoliants, and herbicides); cement formulations for construction use; wet or dry coatings materials (including, but not limited to, paints and dry powder coatings formulations); in ink formulations for the printing industry; in asphalt emulsions used in the paving industry, sewage treatment facilities, etc.
  • test solution 100 grams is charged to a Waring Blender and mixed at the low speed setting for 10 seconds.
  • the contents of the blender are transferred immediately to a 1000 ml graduate cylinder and the foam height determined on the scale.
  • the Waring blender foam heights are given in FIG. 2.
  • the effective products tested in this example were Jeffamine® products D-2000, D-4000, and T-5000.
  • the results of this example indicate that in one embodiment, favorable defoaming characteristics may be achieved with a molecule that is multifunctional, relatively high molecular weight and based predominantly on propylene oxide.
  • a 0.5% by weight active solution of sodium linear alkyl benzene sulfonate (“NaLAS", and in this case Huntsman “ALKYLATE 225TM”) was prepared in DI water with progressively increasing concentration of various amine compounds. 200 ml of each solution was charged to a Waring blender and mixed at low speed for 10 seconds. The results are shown in Table 8 below. With no added amine compound, the control 0.5% NaLAS solution produced approximately 1000 ml of foam. For the amine compound-containing solutions, 4% by weight of various identified amines were added to samples of the 0.5% NaLAS solution. The results of this example show that ethoxylated versions of the JEFFAMINE amines are also effective at defoaming aqueous solutions containing anionic surfactants.
  • multifunctional polyetheramines disclose herein and having one or more primary amine groups may be alkoxylated using methods know in the art.
  • a di-amine having two primary amine groups such as Jeffamine D-2000
  • alkylene oxide such as ethylene oxide
  • Further alkoxylation may be achieved with the use of a catalyst such as NaOH or KOH. While the invention may be adaptable to various modifications and alternative forms, specific embodiments have been shown by way of example and described herein.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Materials Engineering (AREA)
  • Wood Science & Technology (AREA)
  • Toxicology (AREA)
  • Dispersion Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Detergent Compositions (AREA)
  • Degasification And Air Bubble Elimination (AREA)

Abstract

La présente invention concerne des compositions tensioactives anioniques contenant au moins un agent antimousse sous forme d'un ou de plusieurs polyétheramines à plusieurs fonctions. Ces compositions peuvent être formulées avec un ou plusieurs tensioactifs tels que les akylbenzènes sulfonates, et elles peuvent éventuellement être adsorbées sur un vecteur solide tel qu'un matériau à base de silicate de magnésium.
PCT/US2001/011142 2000-04-06 2001-04-06 Compositions antimousse et utilisations pour de telles compositions WO2001076729A2 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
AU2001253179A AU2001253179A1 (en) 2000-04-06 2001-04-06 Defoamer compositions and uses therefor

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US54352900A 2000-04-06 2000-04-06
US09/543,529 2000-04-06

Publications (2)

Publication Number Publication Date
WO2001076729A2 true WO2001076729A2 (fr) 2001-10-18
WO2001076729A3 WO2001076729A3 (fr) 2002-10-03

Family

ID=24168422

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/US2001/011142 WO2001076729A2 (fr) 2000-04-06 2001-04-06 Compositions antimousse et utilisations pour de telles compositions

Country Status (2)

Country Link
AU (1) AU2001253179A1 (fr)
WO (1) WO2001076729A2 (fr)

Cited By (27)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2005021613A1 (fr) * 2003-08-27 2005-03-10 Basf Aktiengesellschaft Agent de regularisation de mousse a base d'oligomeres d'urethanne cationique
US20100264359A1 (en) * 2007-09-26 2010-10-21 Lanxess Deutschland Gmbh Biocidal mixtures
JP2013202518A (ja) * 2012-03-28 2013-10-07 Neos Co Ltd 水溶性消泡剤および低泡性加工油剤
US20140296124A1 (en) * 2013-03-28 2014-10-02 The Procter & Gamble Company Cleaning compositions containing a polyetheramine, a soil release polymer, and a carboxymethylcellulose
WO2014154783A1 (fr) 2013-03-28 2014-10-02 Basf Se Polyétheramines à base de 1,3-dialcools
EP2842936A1 (fr) 2013-08-26 2015-03-04 Basf Se Étheramines basées sur de la glycérine alcoxylée ou du triméthylolpropane
WO2015148890A1 (fr) * 2014-03-27 2015-10-01 The Procter & Gamble Company Compositions de nettoyage contenant une polyétheramine
EP2940116A1 (fr) * 2014-04-30 2015-11-04 The Procter and Gamble Company Composition détergente
EP2940117A1 (fr) * 2014-04-30 2015-11-04 The Procter and Gamble Company Composition de nettoyage contenant un polyéthéramine
WO2016044200A1 (fr) * 2014-09-15 2016-03-24 The Procter & Gamble Company Compositions détergentes contenant des sels de polyétheramines et d'acide polymère
WO2016048674A1 (fr) * 2014-09-25 2016-03-31 The Procter & Gamble Company Compositions de nettoyage contenant une polyétheramine
WO2016049388A1 (fr) * 2014-09-25 2016-03-31 The Procter & Gamble Company Compositions d'entretien de tissus contenant une polyétheramine
WO2016048970A1 (fr) * 2014-09-25 2016-03-31 The Procter & Gamble Company Composition liquide de détergent à lessive
WO2016048969A1 (fr) * 2014-09-25 2016-03-31 The Procter & Gamble Company Compositions détergentes contenant une polyétheramine et un polymère anionique détachant les salissures
US9388368B2 (en) 2014-09-26 2016-07-12 The Procter & Gamble Company Cleaning compositions containing a polyetheramine
JP2016534205A (ja) * 2013-08-26 2016-11-04 ザ プロクター アンド ギャンブル カンパニー ポリエーテルアミンを含有する洗浄組成物
US9677032B2 (en) 2014-04-30 2017-06-13 The Procter & Gamble Company Cleaning composition
US9719052B2 (en) 2014-03-27 2017-08-01 The Procter & Gamble Company Cleaning compositions containing a polyetheramine
US9725682B2 (en) 2014-04-30 2017-08-08 The Procter & Gamble Company Cleaning composition
US9752101B2 (en) 2014-09-25 2017-09-05 The Procter & Gamble Company Liquid laundry detergent composition
WO2017162476A1 (fr) 2016-03-24 2017-09-28 Basf Se Étheramines à base de 1,3-dialcools
US9868925B2 (en) 2014-04-30 2018-01-16 The Procter & Gamble Company Cleaning composition
WO2018077649A1 (fr) * 2016-10-26 2018-05-03 Basf Se Compositions détergentes sans phosphate et leurs applications
US20180179145A1 (en) * 2014-03-27 2018-06-28 Basf Se Etheramines based on dialcohols
US10414856B2 (en) 2014-09-25 2019-09-17 Basf Se Polyetheramines based on 1,3-dialcohols
JP2020014973A (ja) * 2018-07-23 2020-01-30 株式会社ニッコー化学研究所 消泡剤組成物
US11268047B2 (en) 2016-03-24 2022-03-08 The Procter & Gamble Company Compositions containing an etheramine

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3165477A (en) * 1962-01-10 1965-01-12 Dow Chemical Co Process for inhibiting foaming in an aqueous fluid
GB1060559A (en) * 1965-01-21 1967-03-08 Henkel & Cie Gmbh Alkaline cleansing and rinsing agents
US3696057A (en) * 1969-09-03 1972-10-03 Henkel & Cie Gmbh Anti-foaming compositions and cleaning compositions containing them
US4075130A (en) * 1976-08-30 1978-02-21 Texaco Development Corporation Polyoxypropylene polyamine derivatives as defoamers
EP0111984A2 (fr) * 1982-12-23 1984-06-27 THE PROCTER & GAMBLE COMPANY Polymères d'amines éthoxylées ayant des propriétés pour enlever des taches et la contre-redéposition utilisables dans des compositions détergentes

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3165477A (en) * 1962-01-10 1965-01-12 Dow Chemical Co Process for inhibiting foaming in an aqueous fluid
GB1060559A (en) * 1965-01-21 1967-03-08 Henkel & Cie Gmbh Alkaline cleansing and rinsing agents
US3696057A (en) * 1969-09-03 1972-10-03 Henkel & Cie Gmbh Anti-foaming compositions and cleaning compositions containing them
US4075130A (en) * 1976-08-30 1978-02-21 Texaco Development Corporation Polyoxypropylene polyamine derivatives as defoamers
EP0111984A2 (fr) * 1982-12-23 1984-06-27 THE PROCTER & GAMBLE COMPANY Polymères d'amines éthoxylées ayant des propriétés pour enlever des taches et la contre-redéposition utilisables dans des compositions détergentes

Cited By (68)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2005021613A1 (fr) * 2003-08-27 2005-03-10 Basf Aktiengesellschaft Agent de regularisation de mousse a base d'oligomeres d'urethanne cationique
US7807725B2 (en) 2003-08-27 2010-10-05 Basf Aktiengesellschaft Foam regulating agent based on cationic urethane oligomers
US20100264359A1 (en) * 2007-09-26 2010-10-21 Lanxess Deutschland Gmbh Biocidal mixtures
JP2013202518A (ja) * 2012-03-28 2013-10-07 Neos Co Ltd 水溶性消泡剤および低泡性加工油剤
US9540592B2 (en) 2013-03-28 2017-01-10 The Procter & Gamble Company Cleaning compositions containing a polyetheramine, a soil release polymer, and a carboxymethylcellulose
CN105073966A (zh) * 2013-03-28 2015-11-18 宝洁公司 包含聚醚胺的清洁组合物
WO2014160820A1 (fr) * 2013-03-28 2014-10-02 The Procter & Gamble Company Compositions de nettoyage contenant une polyétheramine
WO2014154783A1 (fr) 2013-03-28 2014-10-02 Basf Se Polyétheramines à base de 1,3-dialcools
US20140296124A1 (en) * 2013-03-28 2014-10-02 The Procter & Gamble Company Cleaning compositions containing a polyetheramine, a soil release polymer, and a carboxymethylcellulose
WO2014160821A1 (fr) * 2013-03-28 2014-10-02 The Procter & Gamble Company Compositions de nettoyage contenant une polyétheramine, un polymère de libération des salissures et une carboxyméthylcellulose
JP2016519184A (ja) * 2013-03-28 2016-06-30 ザ プロクター アンド ギャンブル カンパニー ポリエーテルアミンを含有する洗浄組成物
US10633328B2 (en) 2013-03-28 2020-04-28 Basf Se Polyetheramines based on 1,3-dialcohols
US10577564B2 (en) 2013-03-28 2020-03-03 The Procter & Gamble Company Cleaning compositions containing a polyetheramine
CN105102600A (zh) * 2013-03-28 2015-11-25 宝洁公司 包含聚醚胺、去垢性聚合物和羧甲基纤维素的清洁组合物
AU2014241193B2 (en) * 2013-03-28 2016-10-20 The Procter And Gamble Company Cleaning compositions containing a polyetheramine
US9193939B2 (en) 2013-03-28 2015-11-24 The Procter & Gamble Company Cleaning compositions containing a polyetheramine, a soil release polymer, and a carboxymethylcellulose
WO2015028193A1 (fr) 2013-08-26 2015-03-05 Basf Se Étheramines à base de glycérine alcoxylée ou de triméthylolpropane
JP2016531135A (ja) * 2013-08-26 2016-10-06 ビーエーエスエフ ソシエタス・ヨーロピアＢａｓｆ Ｓｅ アルコキシル化グリセリン又はトリメチロールプロパンをベースとするエーテルアミン
JP2016534205A (ja) * 2013-08-26 2016-11-04 ザ プロクター アンド ギャンブル カンパニー ポリエーテルアミンを含有する洗浄組成物
US9932293B2 (en) 2013-08-26 2018-04-03 Basf Se Etheramines based on alkoxylated glycerine or trimethylolpropane
EP2842936A1 (fr) 2013-08-26 2015-03-04 Basf Se Étheramines basées sur de la glycérine alcoxylée ou du triméthylolpropane
US9550965B2 (en) 2013-08-26 2017-01-24 The Procter & Gamble Company Cleaning compositions containing a polyetheramine
US10414719B2 (en) 2014-03-27 2019-09-17 Basf Se Etheramines based on dialcohols
JP2017509754A (ja) * 2014-03-27 2017-04-06 ザ プロクター アンド ギャンブル カンパニー ポリエーテルアミンを含有する洗浄組成物
US9719052B2 (en) 2014-03-27 2017-08-01 The Procter & Gamble Company Cleaning compositions containing a polyetheramine
US9771547B2 (en) 2014-03-27 2017-09-26 The Procter & Gamble Company Cleaning compositions containing a polyetheramine
US20180179145A1 (en) * 2014-03-27 2018-06-28 Basf Se Etheramines based on dialcohols
CN106164235A (zh) * 2014-03-27 2016-11-23 宝洁公司 包含聚醚胺的清洁组合物
CN106164235B (zh) * 2014-03-27 2020-01-31 宝洁公司 包含聚醚胺的清洁组合物
WO2015148890A1 (fr) * 2014-03-27 2015-10-01 The Procter & Gamble Company Compositions de nettoyage contenant une polyétheramine
US9868925B2 (en) 2014-04-30 2018-01-16 The Procter & Gamble Company Cleaning composition
US20150315524A1 (en) * 2014-04-30 2015-11-05 The Procter & Gamble Company Cleaning composition containing a polyetheramine
US10876075B2 (en) 2014-04-30 2020-12-29 The Procter & Gamble Company Cleaning composition
EP2940116A1 (fr) * 2014-04-30 2015-11-04 The Procter and Gamble Company Composition détergente
EP2940117A1 (fr) * 2014-04-30 2015-11-04 The Procter and Gamble Company Composition de nettoyage contenant un polyéthéramine
WO2015167837A1 (fr) * 2014-04-30 2015-11-05 The Procter & Gamble Company Composition de détergent
US9637710B2 (en) 2014-04-30 2017-05-02 The Procter & Gamble Company Cleaning composition containing a polyetheramine
JP2019023311A (ja) * 2014-04-30 2019-02-14 ザ プロクター アンド ギャンブル カンパニー 洗剤組成物
US10190078B2 (en) 2014-04-30 2019-01-29 The Procter & Gamble Company Detergent
JP2017514940A (ja) * 2014-04-30 2017-06-08 ザ プロクター アンド ギャンブル カンパニー 洗剤組成物
US9677032B2 (en) 2014-04-30 2017-06-13 The Procter & Gamble Company Cleaning composition
WO2015168373A1 (fr) * 2014-04-30 2015-11-05 The Procter & Gamble Company Compositions de nettoyage contenant une polyétheramine
US9725682B2 (en) 2014-04-30 2017-08-08 The Procter & Gamble Company Cleaning composition
WO2016044200A1 (fr) * 2014-09-15 2016-03-24 The Procter & Gamble Company Compositions détergentes contenant des sels de polyétheramines et d'acide polymère
US9617502B2 (en) 2014-09-15 2017-04-11 The Procter & Gamble Company Detergent compositions containing salts of polyetheramines and polymeric acid
CN106661515A (zh) * 2014-09-15 2017-05-10 宝洁公司 包含聚醚胺和聚合酸的盐的洗涤剂组合物
US9850452B2 (en) 2014-09-25 2017-12-26 The Procter & Gamble Company Fabric care compositions containing a polyetheramine
WO2016048969A1 (fr) * 2014-09-25 2016-03-31 The Procter & Gamble Company Compositions détergentes contenant une polyétheramine et un polymère anionique détachant les salissures
US10676696B2 (en) 2014-09-25 2020-06-09 The Procter & Gamble Company Liquid laundry detergent composition
CN107075413A (zh) * 2014-09-25 2017-08-18 宝洁公司 液体衣物洗涤剂组合物
WO2016048674A1 (fr) * 2014-09-25 2016-03-31 The Procter & Gamble Company Compositions de nettoyage contenant une polyétheramine
JP2017526796A (ja) * 2014-09-25 2017-09-14 ザ プロクター アンド ギャンブル カンパニー ポリエーテルアミンを含有する洗浄組成物
WO2016049388A1 (fr) * 2014-09-25 2016-03-31 The Procter & Gamble Company Compositions d'entretien de tissus contenant une polyétheramine
WO2016048970A1 (fr) * 2014-09-25 2016-03-31 The Procter & Gamble Company Composition liquide de détergent à lessive
US10174274B2 (en) 2014-09-25 2019-01-08 The Procter & Gamble Company Cleaning compositions containing a polyetheramine
CN107075423A (zh) * 2014-09-25 2017-08-18 宝洁公司 包含聚醚胺的清洁组合物
US9752101B2 (en) 2014-09-25 2017-09-05 The Procter & Gamble Company Liquid laundry detergent composition
US10414856B2 (en) 2014-09-25 2019-09-17 Basf Se Polyetheramines based on 1,3-dialcohols
US9487739B2 (en) 2014-09-25 2016-11-08 The Procter & Gamble Company Cleaning compositions containing a polyetheramine
US9631163B2 (en) 2014-09-25 2017-04-25 The Procter & Gamble Company Liquid laundry detergent composition
CN106661511A (zh) * 2014-09-26 2017-05-10 宝洁公司 包含聚醚胺的清洁组合物
US9388368B2 (en) 2014-09-26 2016-07-12 The Procter & Gamble Company Cleaning compositions containing a polyetheramine
WO2017162476A1 (fr) 2016-03-24 2017-09-28 Basf Se Étheramines à base de 1,3-dialcools
US11268047B2 (en) 2016-03-24 2022-03-08 The Procter & Gamble Company Compositions containing an etheramine
US11274267B2 (en) 2016-03-24 2022-03-15 The Procter & Gamble Company Compositions containing an etheramine
WO2018077649A1 (fr) * 2016-10-26 2018-05-03 Basf Se Compositions détergentes sans phosphate et leurs applications
JP2020014973A (ja) * 2018-07-23 2020-01-30 株式会社ニッコー化学研究所 消泡剤組成物
JP7187005B2 (ja) 2018-07-23 2022-12-12 株式会社ニッコー化学研究所 消泡剤組成物

Also Published As

Publication number Publication date
AU2001253179A1 (en) 2001-10-23
WO2001076729A3 (fr) 2002-10-03

Similar Documents

Publication Publication Date Title
WO2001076729A2 (fr) Compositions antimousse et utilisations pour de telles compositions
JP5405474B2 (ja) 内側ポリエチレンオキシドブロックと外側ポリプロピレンオキシドブロックとを持つ両親媒性水溶性ポリアルキレンイミンを有する洗浄組成物
US6617303B1 (en) Surfactant compositions containing alkoxylated amines
RU2444564C2 (ru) Композиции чистящих средств, содержащие многополимерную систему, включающую по меньшей мере один алкоксилированный жироудаляющий полимер
CA1220395A (fr) Composes detersifs contenant des amines ethoxylees pour detacher la glaise et l'empecher de se redeposer
FI87087C (fi) Rikligt loeddrande flytande tvaettmedelskomposition
US6846793B1 (en) Cleaning concentrate
JP4937996B2 (ja) アルコキシル化ポリアルキレンイミン類を有する洗浄組成物
IE833038L (en) Detergent compositions containing ethoxylated amines
JP2011503284A (ja) アルコキシル化ポリアルカノールアミンを有する洗浄組成物
RU2008142867A (ru) Жидкая моющая композиция для улучшения удаления жировых загрязнений
MX2007001670A (es) Composicion detergente solida altamente soluble en agua que forma un licor de lavado cristalino cuando se disuelve en agua.
BRPI0712934A2 (pt) composiÇÕes detergentes lÍquidas com polÍmeros À base de Ácido poliacrÍlico de baxia polidispercidade
CN114364781A (zh) 具有清洁增强剂的液体衣物洗涤剂
JP2008523226A (ja) 改良された疎水性汚れ洗浄のための親水性変性ポリオール
EP4157978B1 (fr) Composition liquide de lavage de linge
US20090305940A1 (en) Washing amd cleaning agents containing alcohol ethoxylate propoxylates
CN102834501A (zh) 用于制备洗涤剂基础组合物的方法
FI63058B (fi) Flytande buffrad detergentkomposition samt foerfarande foer des framstaellning
JP6930850B2 (ja) 液体洗浄剤組成物
WO2001000758A2 (fr) Melanges tensio-actifs concentres
WO2008112890A1 (fr) Compositions de nettoyage biodégradables
EP3921402A1 (fr) Perfectionnements se rapportant au nettoyage de tissus
EP0815188B1 (fr) Detergent alcalin a haute teneur en tensioactif non-ionique et agent complexant et utilisation d'un composant amphotere comme agent de solubilisation
JP6967939B2 (ja) 液体洗浄剤

Legal Events

Date Code Title Description
AK Designated states

Kind code of ref document: A2

Designated state(s): AE AG AL AM AT AU AZ BA BB BG BR BY BZ CA CH CN CR CU CZ DE DK DM DZ EE ES FI GB GD GE GH GM HR HU ID IL IN IS JP KE KG KP KR KZ LC LK LR LS LT LU LV MA MD MG MK MN MW MX MZ NO NZ PL PT RO RU SD SE SG SI SK SL TJ TM TR TT TZ UA UG UZ VN YU ZA ZW

AL Designated countries for regional patents

Kind code of ref document: A2

Designated state(s): GH GM KE LS MW MZ SD SL SZ TZ UG ZW AM AZ BY KG KZ MD RU TJ TM AT BE CH CY DE DK ES FI FR GB GR IE IT LU MC NL PT SE TR BF BJ CF CG CI CM GA GN GW ML MR NE SN TD TG

121 Ep: the epo has been informed by wipo that ep was designated in this application
DFPE Request for preliminary examination filed prior to expiration of 19th month from priority date (pct application filed before 20040101)
AK Designated states

Kind code of ref document: A3

Designated state(s): AE AG AL AM AT AU AZ BA BB BG BR BY BZ CA CH CN CR CU CZ DE DK DM DZ EE ES FI GB GD GE GH GM HR HU ID IL IN IS JP KE KG KP KR KZ LC LK LR LS LT LU LV MA MD MG MK MN MW MX MZ NO NZ PL PT RO RU SD SE SG SI SK SL TJ TM TR TT TZ UA UG UZ VN YU ZA ZW

AL Designated countries for regional patents

Kind code of ref document: A3

Designated state(s): GH GM KE LS MW MZ SD SL SZ TZ UG ZW AM AZ BY KG KZ MD RU TJ TM AT BE CH CY DE DK ES FI FR GB GR IE IT LU MC NL PT SE TR BF BJ CF CG CI CM GA GN GW ML MR NE SN TD TG

122 Ep: pct application non-entry in european phase
NENP Non-entry into the national phase

Ref country code: JP