WO1995033033A1 - Compositions de detergents lessiviels - Google Patents

Compositions de detergents lessiviels Download PDF

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Publication number
WO1995033033A1
WO1995033033A1 PCT/US1995/006523 US9506523W WO9533033A1 WO 1995033033 A1 WO1995033033 A1 WO 1995033033A1 US 9506523 W US9506523 W US 9506523W WO 9533033 A1 WO9533033 A1 WO 9533033A1
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Prior art keywords
formula
alkyl
cationic surfactant
surfactant
cationic
Prior art date
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PCT/US1995/006523
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English (en)
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WO1995033033A9 (fr
Inventor
Barry Thomas Ingram
Alison Lesley Main
Christian Leo Marie Vermote
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The Procter & Gamble Company
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Priority to EP95920624A priority Critical patent/EP0763091A1/fr
Priority to MX9606046A priority patent/MX9606046A/es
Priority to JP8500999A priority patent/JPH10501279A/ja
Publication of WO1995033033A1 publication Critical patent/WO1995033033A1/fr
Publication of WO1995033033A9 publication Critical patent/WO1995033033A9/fr

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    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
    • C11D1/38—Cationic compounds
    • C11D1/65—Mixtures of anionic with cationic 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
    • C11D1/86—Mixtures of anionic, cationic, and non-ionic 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
    • C11D1/02—Anionic compounds
    • C11D1/04—Carboxylic acids or salts thereof
    • C11D1/10—Amino carboxylic acids; Imino carboxylic acids; Fatty acid condensates thereof
    • 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
    • C11D1/02—Anionic compounds
    • C11D1/12—Sulfonic acids or sulfuric acid esters; Salts thereof
    • C11D1/14—Sulfonic acids or sulfuric acid esters; Salts thereof derived from aliphatic hydrocarbons or mono-alcohols
    • 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
    • C11D1/02—Anionic compounds
    • C11D1/12—Sulfonic acids or sulfuric acid esters; Salts thereof
    • C11D1/22—Sulfonic acids or sulfuric acid esters; Salts thereof derived from aromatic 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
    • C11D1/02—Anionic compounds
    • C11D1/12—Sulfonic acids or sulfuric acid esters; Salts thereof
    • C11D1/29—Sulfates of polyoxyalkylene ethers
    • 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
    • C11D1/38—Cationic compounds
    • C11D1/52—Carboxylic amides, alkylolamides or imides or their condensation products with alkylene oxides
    • C11D1/525—Carboxylic amides (R1-CO-NR2R3), where R1, R2 or R3 contain two or more hydroxy groups per alkyl group, e.g. R3 being a reducing sugar rest
    • 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
    • C11D1/38—Cationic compounds
    • C11D1/62—Quaternary ammonium 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

Definitions

  • This invention relates to laundry detergent compositions which exhibit improved greasy and oily soil and body soil removal capabilities.
  • the compositions are generally free of phosphate; alternatively, they may contain low levels of phosphate materials but not amounts in excess of about 20% by weight.
  • These detergent compositions provide an unexpectedly high level of greasy and oil soil (such as motor oil, triolein, animal fat and lipstick) removal; they also provide excellent removal of particulate soils, especially clay soils, as well as fabric care benefits, such as fabric softening, static control, and dye transfer inhibition.
  • Oleoyl sarcosinate is a known anionic surfactant which has been used as the detersive surfactant in fabric laundering compositions.
  • Oleoyl sarcosinate has been described in the following patents and publications: U.S. 2,542,385; U.S. 3,402,990; U.S. 3,639,568; U.S. 4,772,424; U.S. 5,186,855; European Patent Publication 505,129; British Patent Publication 1,211,545; Japanese Patent Publication 59/232194; Japanese Patent Publication 62/295997; Japanese Patent Publication 02/180811; and Chemical Abstracts Service Abstracts Nos. 61:3244q, 70:58865x, and 83:181020p.
  • Cationic surfactants have also been used in detergent compositions primarily to provide adjunct fabric care benefits and not for the purpose of enhancing cleaning.
  • Certain cationic surfactants provide a germicidal or sanitization benefit to washed surfaces; see for example, U.S. Pat. No. 2,742,434, Koop, issued Apr. 17, 1956; U.S. Pat. No. 3,539,520, Cantor et al, issued Nov. 10, 1970; and U.S. Pat. No. 3,965,026, Lancz, issued June 22, 1976.
  • Other cationic surfactants such as ditallowalkyldimethylammonium chloride, are included in detergent compositions to provide a fabric softening benefit, as disclosed in U.S. Pat. No.
  • compositions of the present invention have outstanding cleaning capabilities. Such compositions can be very effective in removing some typical greasy and oily soils in comparison with conventional laundry detergents, including commercially-available heavy duty liquid detergents containing a high proportion of nonionic surfactants. These same detergent compositions, with or without phosphate or other builder components, are also effective in removing clay soils at least as well, and in some instances, substantially better than fully-built conventional granular laundry detergent compositions, and, in addition provide a range of fabric care benefits, such as fabric softening, static control and dye transfer inhibition, to the laundered fabrics. Thus, the compositions of the present invention provide the user with a well-rounded cleaning and fabric care package. These are the result of a heretofore unrecognized cleaning potential provided by the combination of selected anionic surfactants, i.e. oleoyl sarcosinates, and certain selected cationic surfactants.
  • selected anionic surfactants i.e. oleoyl sarc
  • the present invention relates to laundry detergent compositions that comprise from about 5% to 100%, by weight, of a surfactant mixture comprising: (A) an oleoyl sarcosinate of the formula: C 17 H33C(O)N(CH3)CH 2 COOM wherein M is hydrogen or a cationic moiety; and (B) a specific type of cationic surfactant which is free of hydrazinium groups.
  • a surfactant mixture comprising: (A) an oleoyl sarcosinate of the formula: C 17 H33C(O)N(CH3)CH 2 COOM wherein M is hydrogen or a cationic moiety; and (B) a specific type of cationic surfactant which is free of hydrazinium groups.
  • Such cationic surfactants have the formula wherein R! is an organic group containing a straight or branched alkyl or alkenyl group optionally substituted with up to 3 phenyl or hydroxy groups and optionally interrupted by
  • each Rl containing about 8 to about 22 carbon atoms, and which may additionally contain up to about 12 ethylene oxide groups
  • m is a number from 1 to 3
  • each R ⁇ is an alkyl or hydroxy alkyl group containing from 1 to 4 carbon atoms or a benzyl group, with no more than one R ⁇ in a molecule being benzyl
  • x is from 0 to 11, the remainder of any carbon atom positions being filled by hydrogens
  • Y is selected from
  • L is 1 or 2
  • the Y groups being separated b a moiety selected from R 1 and R ⁇ analogs having from one to about twenty-two carbon atoms and 2 free carbon single bonds when L is 2, and Z is an anion in a number sufficient to give electrical neutrality.
  • These cationic surfactants should be at least substantially water dispersible in admixture with the oleoyl sarcosinate surfactant,
  • compositions of this invention provide a pH of at least about 6.5 in aqueous laundry solution.
  • the ratio of oleoyl sarcosinate surfactant to cationic surfactant ranges from about 1:1 to 100:1.
  • the present invention also relates to a process for cleaning fabrics soiled with greasy and/or oily soils.
  • Such a process comprises contacting such soiled fabrics with an aqueous solution containing water and from about 0.1% to 1% of the oleoyl sarcosinate/cationic surfactant combinations hereinbefore described.
  • Fabric pretreatment processes are also provided.
  • One essential component of the surfactant mixture employed in the detergent compositions herein is the anionic surfactant oleoyl sarcosinate in its acid and/or salt form.
  • the oleoyl sarcosinate will comprise from about 0.1% to about 80%, more preferably from about 1% to about 40%, and most preferably about 2% to about 30% by weight of the compositions.
  • Oleoyl sarcosinate has the general formula: Ci 7H33C(O)N(CH3)CH2COOM wherein M is hydrogen or a cationic moiety.
  • the configuration of oleoyl sarcosinates can be represented as follows
  • Preferred M substituents are hydrogen and alkali metal cations, especially sodium and potassium.
  • Oleoyl sarcosinate is commercially available, for example as Hamposyl O marketed by W. R. Grace & Co.
  • oleoyl sarcosinate useful herein can also be prepared from the ester (preferably the methyl ester) or oleic acid and a sarcosine salt (preferably the sodium salt) under anhydrous reaction conditions in the presence of a base catalyst with a basicity equal to or greater than alkoxide catalyst (preferably sodium methoxide).
  • a base catalyst with a basicity equal to or greater than alkoxide catalyst (preferably sodium methoxide).
  • alkoxide catalyst preferably sodium methoxide
  • This salt may be optionally neutralized to form the oleoyl sarcosinate in its acid form.
  • the preferred method for preparing oleoyl sarcosinate is conducted at a temperature from about 80°C to about 200°C, especially from about 120°C to about 200°C. It is preferred to conduct the reaction without solvent although alcohol solvents which have a boiling point of at least 100°C and are stable to the reaction conditions (i.e., glycerol is not acceptable) can be used.
  • the reaction may proceed in about 85% yield with a molar ratio of methyl ester reactant to sarcosine salt reactant to basic catalyst of about 1 : 1 :0.05-0.2.
  • Methyl ester mixtures derived from high oleic content natural oils are especially preferred as starting materials. Examples include high-oleic sunflower and rapeseed/canola oil. In addition, a high- oleic methyl ester fraction derived from either palm kernel oil or tallow is acceptable. It is to be understood that such oils typically will contain some levels of impurities, including some fatty acid impurities that may be converted to sarcosinate compounds by this synthesis method.
  • commodity canola/rapeseed oil may comprise a majority of oleic acid, and a mixture of fatty acid impurities such as palmitic, stearic, linoleic, linolenic and/or eicosenoic acid, some or all of which are converted to the sarcosinate by this reaction method. If desired for formulation purposes, some or all of such impurity materials may be excluded from the starting oil before preparing the oleoyl sarcosinate to be used in the present invention.
  • sarcosine remaining in the reaction mixture can be converted to an amide by addition of maleic or acetic anhydride to the mixture, thereby minimizing the sarcosine content and any potential for formation of undesired nitrogen- containing impurities.
  • the synthesis of oleoyl sarcosinate may be carried out as follows to prepare the sodium oleoyl sarcosinate.
  • reaction mixture is heated to 170°C for 1 hr. to drive off any water.
  • the reaction is initiated by the addition of sodium methoxide 25% in methanol (15.4 g, 0.0714 mol).
  • the reaction mixture is kept at 170°C for 2.5 hr. during which methanol is collected in the Dean-Stark trap.
  • the reaction is allowed to cool slightly, and then methanol (200 g) is added.
  • Maleic anhydride (9.43 g, 0.095 mol) is added to the methanol solution, and the reaction is stirred at 60°C for 0.5 hr.
  • the second essential component of the surfactant mixture employed herein is a certain type of cationic surfactant material.
  • cationics are those of the general formula W ⁇ W ⁇ YiZ wherein the elements of this formula are as described hereinbefore in the Summary of the Invention section.
  • Z is a water-soluble anion such as halide, methyl sulfate, sulfate, or nitrate anion with particularly preferred anions being chloride, bromide, iodide, sulfate, or methyl sulfate, in a number to give electrical neutrality of the cationic component.
  • L is equal to 1, p is from 1 to 12, preferably from 1 to 10, and Y is or mixtures thereof. However, L may be equal to two, thereby yielding cationic components containing two cationic charge centers.
  • An example of a di-cationic component is given below:
  • compositions of this mono-long chain type include those in which R is a CJO to Cjg alkyl group.
  • Particularly preferred components of this class include C ⁇ (palmitylalkyl) trimethylammonium halide, tallowalkyl trimethylammonium halide and coconutalkyl trimethylammonium halide.
  • tallowalkyl trimethylammonium or coconutalkyl trimethylammonium materials are combined with oleoyl sarcosinate in sarcosinate/cationic ratios of from 1:1 to 10:1, more preferably 5:1 to 9:1.
  • Another preferred surfactant mixture utilizes mono- long chain cationic surfactants of the formula
  • Rl, R ⁇ and Z are as defined above, in combination with sarcosinate in sarcosinate: cationic ratios of from 5.1:1 to 15:1.
  • Useful di- long chain cationics include those of the above formula wherein m is 2. When m is equal to 2, it is preferred that x is equal to 2, and that R ⁇ is a methyl group. In this instance it is also preferred that R is a CI Q to C20 alkyl group.
  • Particularly preferred cationic materials of the class include dicoconutalkyl (C12- C14) dimethylammonium halide, distearylalkyl (C j g) dimethylam onium halide and ditallowalkyl (Cig-Cjg) dimethylammonium halide materials.
  • R ⁇ is a methyl group.
  • R ⁇ is a Cg to Cj i alkyl group.
  • Particularly preferred tri-long chain cationic materials include trioctylalkyl (Cg) methyl ammonium halide and tridecyalkyl (C ⁇ Q) methyl ammonium halide.
  • Another preferred type of cationic surfactant useful in the surfactant mixtures employed in the present invention is of the imidazolinium variety.
  • a particularly preferred surfactant of this type is one having the structural formula
  • R is C ⁇ Q to C20 alkyl, particularly C14 to C20 alkyl.
  • imidazolinium surfactants may be used alone as the cationic component in the compositions of the present invention, or may be used in mixtures, together with other cationic surfactants, such as those described above. In these mixtures, it is preferred that the ratio of the imidazolinium surfactant to the other cationic surfactant is from about 4:1 to about 1 :4.
  • Particularly preferred mixtures of this type include the imidazolinium surfactant, shown above, together with palmitylalkyl trimethylammonium chloride or coconutalkyl trimethylammonium chloride or a mixture of coconutalkyl trimethylammonium chloride and palmitylalkyl trimethylammonium chloride.
  • alkoxylated alkyl quaternaries Another type of preferred cationic surfactant for use in the compositions of the present invention are the alkoxylated alkyl quaternaries. Examples of such compounds are given below:
  • each p is from 1 to 12, preferably from 1 to 10 (with the total ethylene oxide groups in a molecule not exceeding about 13), and each R is a CJQ to 20 alkyl group. It is preferred that these compounds contain no more than a total of about 10, preferably no more than about 7, ethylene oxide groups in order to obtain the best removal of greasy and oily soils.
  • the compositions of the present invention are preferably substantially free of cationic compounds containing about 13 or more ethylene oxide groups. These compounds tend to be relatively non-biodegradable, do not enhance the cleaning or fabric conditioning benefits provided by the compositions and may, in some circumstances, decrease the overall laundering performance provided by them. It is to be noted that polyethoxylated cationic surfactants having relatively low levels of ethoxylation, such as those described above, exhibit better biodegradability characteristics and may be advantageously included in the compositions of the present invention.
  • R is Ci to C4 alkyl or hydroxyalkyl
  • R ⁇ is C5 to C30 straight or branched chain alkyl, alkenyl, alkyl phenyl, or
  • R i wherein s is from 0 to 5; R ⁇ is C ⁇ to C20 alkylene or alkenylene; a is 0 to 1, and n is 1 when a is 1; m is from 1 to 5; Z and Z ⁇ are each selected from the group consisting of
  • X is an anion which makes the compound at least water-dispersible, preferably selected from the group consisting of halide, methyl sulfate, sulfate, and nitrate, more preferably chloride, bromide, iodide, methyl sulfate and sulfate.
  • this particular cationic component is environmentally desirable, since it is biodegradable, yielding environmentally acceptable compounds, both in terms of its long alkyl chain and its nitrogen-containing segment.
  • These preferred cationic components when used in the compositions of the present invention, are employed in surfactant mixtures which have sarcosinate to cationic surfactant ratios of from 5.1:1 to about 100:1, particularly from 5.1:1 to about 50:1 most preferably from about 6:1 to 40: 1 , especially from about 6: 1 to about 20: 1.
  • Particularly preferred cationic surfactants of this type are the choline ester derivatives having the following formula:
  • p may be from 0 to 20. 0 0 3
  • the preferred choline-derivative cationic substances may be prepared by the direct esterification of a fatty acid of the desired chain length with dimethylaminoethanol, in the presence of an acid catalyst. The reaction product is then quaternized with a methyl halide, forming the desired cationic material.
  • the choline-derived cationic materials may also be prepared by the direct esterification of a long chain fatty acid of the desired chain length together with 2-haloethanol, in the presence of an acid catalyst material. The reaction product is then used to quaternize trimethylamine, forming the desired cationic component.
  • each Rl is a CI to C4 alkyl or hydroxyalkyl group, preferably a methyl group.
  • Each R ⁇ is either hydrogen or C ⁇ to C3 alkyl, preferably hydrogen.
  • R ⁇ is a C4 to C30 straight or branched chain alkyl, alkenyl, or alkylbenzyl group, preferably a Cg to Cjg alkyl group, most preferably a C12 alkyl group.
  • R ⁇ is a C ⁇ to C10 alkylene or alkenylene group; n is from 2 to 4, preferably 2; y is from 1 to 20, preferably from about 1 to 10, most preferably about 7; a may be 0 or 1, and t may be 0 or 1, but t is 1 when a is 1; and m is from 1 to 5, preferably 2.
  • Z ⁇ is selected from the group consisting
  • Z ⁇ and Z ⁇ groups being selected form the group consisting of ester, reverse ester, amide or reverse amide.
  • X is an anion which makes the compound at least water dispersible, and is selected from the group consisting of halides, methyl sulfate, sulfate, and nitrate, particularly chloride, bromide, iodide, methyl sulfate and sulfate. Mixtures of the above structures can also be used.
  • This particular type of cationic surfactant may be used in sarcosinate/cationic surfactant mixtures in the compositions of the present invention in sarcosinate to cationic ratios of from 5.1:1 to about 100:1, preferably from 5.1:1 to about 50:1, most preferably from about 6:1 to about 40:1, especially from about 6:1 to about 20:1.
  • These surfactants when used in the compositions of the present invention, yield excellent particulate soil, body soil, and greasy and oil soil removal.
  • the detergent compositions control static and soften fabrics laundered therewith, and inhibit the transfer of dyes in the wash solution.
  • these cationic surfactants are environmentally desirable, since both their long chain alkyl segments and their nitrogen segments are biodegradable.
  • Preferred embodiments of this type of cationic component are esters in which Ri is a methyl group and Z ⁇ is an ester or reverse ester group. Particular examples of these compounds are given below, in which t is 0 or 1 and y is from 1 to 20.
  • the preferred derivatives, described above, may be prepared by the reaction of a long chain alkyl polyalkoxy (preferably polyethoxy) carboxylate, having an alkyl chain of desired length, with oxalyl chloride, to form the corresponding acid chloride.
  • the acid chloride is then reacted with dimethylaminoethanol to form the appropriate amine ester, which is then quatemized with a methyl halide to form the desired ester compound.
  • Another way of preparing these compounds is by the direct esterification of the appropriate long chain ethoxylated carboxylic acid together with 2-haloethanol or dimethyl aminoethanol, in the presence of heat and an acid catalyst.
  • the reaction product formed is then quatemized with methylhalide or used to quatemize trimethylamine to form the desired ester compound.
  • compositions of the present invention comprise, by weight, from about 5% to 100%, preferably from about 10% to about 95%, and most preferably from about 20% to about 90% of a mixture of the particularly defined sarcosinate and cationic surfactants described hereinbefore in the ratios stated. It is preferred that the detergent compositions contain at least about 1% of the cationic component; otherwise, sufficient cationic surfactant may not be present in the wash solution to provide the desired cleaning and conditioning results. Further, preferred compositions do not contain more than about 10% of the cationic component, due to cost and commercial availability considerations.
  • detergent compositions herein containing the hereinbefore described sarcosinate/cationic surfactant mixtures, along with other optional detergent composition components described hereinafter, are preferably prepared in accordance with formulation criteria analogous to those such as the "cloud point” and Reduced Monomer Concentration (CR) characteristics of the cationic surfactant, as described in Murphy; U.S. 4,259,217; Issued March 31, 1981.
  • This '217 patent is incorporated herein by reference in its entirety.
  • the detergent compositions herein may also comprise a wide variety of optional ingredients.
  • optional ingredients include optional additional detersive surfactants, builders and other conventional detergent composition adjuvants, a) Optional Detersive Surfactants
  • the detergent compositions herein may optionally comprise from about 1% to 80% by weight of an additional non-sarcosinate, non-cationic detersive surfactant. Preferably such compositions will comprise from about 5% to 50% by weight of this optional surfactant.
  • Optional detersive surfactants utilized can be of the anionic, nonionic, zwitterionic, or ampholytic type or can comprise compatible mixtures of these surfactant types.
  • anionics and nonionics are preferred and non-sarcosinate anionics are most preferred.
  • Such preferred anionic surfactants can themselves be of several different types.
  • water-soluble salts of the higher fatty acids i.e., "soaps"
  • alkali metal soaps such as the sodium, potassium salts and the ammonium, alkylammonium and alkanolamine salts of higher fatty acids containing from about 8 to about 24 carbon atoms, and preferably from about 12 to about 18 carbon atoms.
  • Soaps can be made by direct saponification of fats and oils or by the neutralization of free fatty acids.
  • non-sarcosinate anionic surfactants which suitable for use herein include the water-soluble salts, preferably the alkali metal, ammonium, alkylammonium and alkanolamine salts, or organic sulfuric reaction products having in their molecular structure an alkyl group containing from about 10 to about 20 carbon atoms and a sulfonic acid or sulfuric acid ester group.
  • alkyl is the alkyl portion of acyl groups.
  • this group of synthetic surfactants are a) the sodium, potassium and ethanolamine alkyl sulfates, especially those obtained by sulfating the higher alcohols (Cg-Ci g carbon atoms) such as those produced by reducing the glycerides of tallow or coconut oil; b) the sodium, potassium and ethanolamine alkyl polyethoxylate sulfates, particularly those in which the alkyl group contains from 10 to 22, preferably from 12 to 18 carbon atoms, and wherein the polyethoxylate chain contains from 1 to 15, preferably 1 to 6 ethoxylate moieties; and c) the sodium and potassium alkylbenzene sulfonates in which the alkyl group contains from about 9 to about 15 carbon atoms, in straight chain or branched chain configuration, e.g., those of the type described in U.S.
  • Especially valuable are linear straight chain alkylbenzene sulfonates in which the average number of carbon atoms in the alkyl group is from about 11 to 13, abbreviated as Ci j_i3 LAS.
  • Preferred optional nonionic surfactants are those of the formula R 1 (OC2H4) n OH, wherein R 1 is a CJO-CIO alkyl group or a Cg-Cj2 alkyl phenyl group, and n is from 3 to about 80.
  • Particularly preferred are condensation products of Ci2 _ Ci5 alcohols with from about 3 to about 20 moles of ethylene oxide per mole of alcohol, e.g., C12-C13 alcohol condensed with about 6.5 moles of ethylene oxide per mole of alcohol.
  • Additional suitable nonionic surfactants include polyhydroxy fatty acid amides of the formula
  • R is a C9.17 alkyl or alkenyl
  • Rj is a preferably a methyl or 3- methoxypropyl group
  • Z is glycityl derived from a reduced sugar or alkoxylated derivative thereof.
  • Examples are N-methyl N-1-deoxyglucityl cocoamide and N- methyl N-1-deoxyglucityl oleamide and other C12-C18 N-methylglucamides. See WO 9,206,154.
  • Other sugar-derived surfactants include the N-alkoxy polyhydroxy fatty acid amides, such as C ⁇ Q-CIS N-(3-methoxypropyl) glucamide.
  • the N-propyl through N-hexyl C12-C18 glucamides can be used for low sudsing.
  • Processes for making polyhydroxy fatty acid amides are known and can be found in Wilson, U.S. Patent 2,965,576 and Schwartz, U.S. Patent 2,703,798, the disclosures of which are incorporated herein by reference, b) Detergent Builder
  • the detergent compositions herein may also optionally comprise from about 0.1% to 80% by weight of a detergent builder.
  • such compositions in liquid form will comprise from about 1% to 10% by weight of the builder component.
  • Preferably such compositions in granular form will comprise from about 1% to 50% by weight of the builder component.
  • Detergent builders are well known in the art and can comprise, for example, phosphate salts as well as various organic and inorganic nonphosphorus builders.
  • Water-soluble, nonphosphorus organic builders useful herein include the various alkali metal, ammonium and substituted ammonium polyacetates, carboxylates, polycarboxylates and polyhydroxy sulfonates.
  • polyacetate and polycarboxylate builders are the sodium, potassium, lithium, ammonium, and substituted ammonium salts of ethylene diamine tetraacetic acid, nitrilotriacetic acid, oxydisuccinic acid, mellitic acid, benzene polycarboxylic acids, and citric acid.
  • Other suitable polycarboxylates for use herein are the polyacetal carboxylates described in U.S.
  • Particularly preferred polycarboxylate builders are the oxydisuccinates and the ether carboxylate builder compositions comprising a combination of tartrate monosuccinate and tartrate disuccinate described in U.S. Patent 4,663,071, Bush et al., issued May 5, 1987, the disclosure of which is incorporated herein by reference.
  • suitable nonphosphorus, inorganic builders include the silicates, aluminosilicates, borates and carbonates.
  • aluminosilicates including zeolites such materials and their use as detergent builders are more fully discussed in Corkill et al., U.S. Patent No. 4,605,509, the disclosure of which is incorporated herein by reference.
  • crystalline layered silicates such as those discussed in Corkill et al., U.S. Patent No. 4,605,509, incorporated herein by reference, are suitable for use in the detergent composition of the invention.
  • the detergent composition of the present invention can also include any number of additional optional ingredients.
  • additional optional ingredients include conventional detergent composition components such as suds boosters or suds suppressers, anti-tarnish and anti-corrosion agents, soil suspending agents, soil release agents, germicides, pH adjusting agents, non-builder alkalinity sources, chelating agents, smectite clays, hardness ions such as Ca " ⁇ and/or Mg " - * " cations, enzymes, enzyme-stabilizing agents and perfumes.
  • Dye transfer inhibiting agents and add optical brighteners may also be included.
  • Chelating agents are described in U.S. Patent 4,663,071, Bush et al., from Column 17, line 54, through Column 18, line 68, incorporated herein by reference. Suds modifiers are also optional ingredients and are described in U.S. Patents 3,933,672, issued January 20, 1976, to Bartoletta et al., and 4,136,045, issued January 23,1979, to Gault et al., both incorporated herein by reference. Suitable smectite clays for use herein are described in U.S. Patent 4,762,645, Tucker et al., issued August 9, 1988, column 6, line 3 through Column 7, line 24, incorporated herein by reference.
  • a preferred biodegradable chelator for use herein is ethylenediamine disuccinate ("EDDS"), especially the [S,S] isomer as described in U.S. Patent 4,704,233, November 3, 1987, to Hartman and Perkins.
  • EDDS ethylenediamine disuccinate
  • the detergent compositions herein may optionally contain bleaching agents or bleaching compositions containing a bleaching agent and one or more bleach activators.
  • bleaching agents will typically be at levels of from about 1% to about 30%, more typically from about 5% to about 20%, of the detergent composition, especially for fabric laundering.
  • the amount of bleach activators will typically be from about 0.1% to about 60%, more typically from about 0.5% to about 40% of the bleaching composition comprising the bleaching agent- plus-bleach activator.
  • Suitable enzyme components are available from a wide variety of commercial sources.
  • suitable enzymes are available from NOVO Industries under product names T-GranulateTM and Savinase TM, and Gist-Brocades under product names MaxacalTM and MaxataseTM. Included within the group of enzymes are proteases, amylases, lipases, cellulases and mixtures thereof.
  • the enzyme concentration preferably should be from about 0% to about 5%, more preferably from about 0.001% to about 2.5%, and most preferably from about 0.01% to about 2%.
  • proteases are used at an Activity Unit (Anson Unit) level of from about 0.001 to about 0.05, most preferably from about 0.002 to about 0.02, while amylases are used at an amylase unit level of from about 5 to about 5000, most preferably from about 50 to about 500 per gram of detergent composition.
  • Activity Unit Asson Unit
  • amylases are used at an amylase unit level of from about 5 to about 5000, most preferably from about 50 to about 500 per gram of detergent composition.
  • proteases are the subtilisins which are obtained from particular strains of B. subtilis and B. licheniforms. Another suitable protease is obtained from a strain of Bacillus, having maximum activity throughout the pH range of 8-12, developed and sold by Novo Industries A S under the registered trade name ESPERASE. The preparation of this enzyme and analogous enzymes is described in British Patent Specification No. 1,243,784 of Novo.
  • protealytic enzymes suitable for removing protein-based stains that are commercially available include those sold under the tradenames ALCALASE and SAVINASE by Novo Industries A/S (Denmark) and MAXATASE by International Bio-Synthetics, Inc. (The Netherlands).
  • proteases include Protease A (see European Patent Application 130,756, published January 9, 1985) and Protease B (see European Patent Application Serial No. 87303761.8, filed April 28, 1987, and European Patent Application 130,756, Bott et al, published January 9, 1985).
  • Other proteases include Protease A (see European Patent Application 130,756, published January 9, 1985) and Protease B (see European Patent Application Serial No. 87303761.8, filed April 28, 1987, and European Patent Application 130,756, Bott et al, published January 9, 1985).
  • Other proteases include Protease A (see European Patent Application 130,756, published January 9, 1985) and Protease B (see European Patent Application Serial No.
  • Protease C is a variant of an alkaline serine protease from Bacillus, particularly Bacillus lentus. in which arginine replaced lysine at position 27, tyrosine replaced valine at position 104, serine replaced asparagine at position 123, and alanine replaced threonine at position 274.
  • Protease C is described in EP 90915958:4; U.S. Patent No. 5,185,250; and U.S. Patent No. 5,204,015.
  • protease which are described in copending application U.S. Serial No.
  • the detergent compositions according to the present invention can be in liquid, gel or granular forms. Such compositions can be prepared by combining the essential and optional components in the requisite concentrations in any suitable order and by an conventional means. Granular compositions, for example, are generally made by combining base granule ingredients (e.g.
  • Granular compositions according to the present invention can also be in "compact form", i.e. greater than about 600 g/1.
  • the granular detergent compositions according to the present invention will contain a lower amount of "inorganic filler salt", compared to conventional granular detergents; typical filler salts are alkali earth metal salts of sulfates and chlorides, typically sodium sulfate; "compact" detergents typically comprise not more than 10% filler salt.
  • Liquid detergent compositions can be prepared by admixing the essential and optional ingredients thereof in any desired order to provide compositions containing components in the requisite concentrations.
  • Liquid compositions according to the present invention can also be in "compact form.” In such case, the liquid detergent compositions according to the present invention will contain a lower amount of water, compared to conventional liquid detergents.
  • the compositions of the present invention are formulated so as to have a pH of at least about 6.5, preferably greater than about 7 in the laundry solution at conventional usage concentrations in order to optimize cleaning performance on greasy and oily soils; acidic wash solution pH's tend to decrease performance on such soils.
  • the compositions herein are more alkaline in nature when placed in the laundry solution and have a pH of greater than about 7.5.
  • compositions should generally be free of oily hydrocarbon materials, such as many dry cleaning solvents, mineral oil, paraffin oil and kerosene, because these materials (which are themselves oily in nature) load the washing liquor with excessive oily material, thereby diminishing the cleaning effectiveness of the compositions of this invention.
  • oily hydrocarbon materials such as many dry cleaning solvents, mineral oil, paraffin oil and kerosene
  • the cationic component should also be free of hydrazinium groups due to their relatively high toxicity level which makes them unsuitable for use in the compositions of this invention.
  • Preferred compositions contain sarcosinate to cationic surfactant ratios of from 5.1:1 to about 50:1, preferably from about 6:1 to about 40:1, particularly from about 6:1 to about 20: 1.
  • Greasy and oil soil removal is greatly enhanced at ratios between about 8:1 to about 20: 1, the improvement in performance generally being most noticeable as the amount of sarcosinate is increased so that the ratio of sarcosinate to cationic surfactant becomes greater than 5.1:1 and approaches 8:1.
  • the present invention also provides a process for laundering fabrics soiled with greasy/oily stains or soil. Such a process employs contacting these fabrics with an aqueous washing solution formed from an effective amount of the detergent compositions hereinbefore described. Contacting of fabrics with washing solution will generally occur under conditions of agitation.
  • Agitation is preferably provided in a washing machine for good cleaning.
  • Washing is preferably followed by drying the wet fabric in a conventional clothes dryer.
  • An effective amount of the liquid or granular detergent composition in the aqueous wash solution in the washing machine is preferably from about 500 to about
  • the detergent compositions herein may also be used to pretreat fabrics containing greasy/oily soils or stains prior to washing such fabrics using conventional aqueous washing solutions.
  • Such pretreatment involves the application of highly concentrated forms of the detergent compositions herein directly onto the greasy or oily stains or soils found on the fabric to be cleaned.
  • compositions herein in liquid or gel form this will generally involve the direct application of the composition as is to the stain/soil on the fabric.
  • pretreatment involves the application of an aqueous paste formed from such granular products.
  • Aqueous pastes of this type will generally contain from about 1% to 50% water, preferably from about 5% to 20% water.
  • Pretreatment of greasy/oily stains or soils will generally occur for a period of from about 30 seconds to 24 hours prior to washing the pretreated soiled/stained substrate in conventional manner. More preferably, pretreatment times will range from about 1 to 180 minutes.
  • Oleoyl sarcosinate 10.0 9.0 3.0 10.0 1 Palmitylalkyl trimethylammonium 5.0 2.3 chloride
  • Enzymes prote, lipase, cellulase
  • Enzymes prote, lipase, cellulase
  • DC 3421 is a silicone oil commercially available from Dow Corning.
  • compositions described in Table I are suitable for laundering fabrics soiled with grease or oil using aqueous washing solutions formed from such compositions.
  • compositions of Table I are also especially effective for pretreating fabrics with greasy or oily stains. To effect such pretreatment, greasy/oily stains and soils on the - -
  • compositions having substantially similar greasy/oily soil removal performance properties are realized when in the above compositions the cationic surfactants are replaced with an equivalent amount of decylalkyl trimethylammonium chloride, decylalkyl trimethylammonium hydroxide, C14 alkyl trimethylammonium chloride, distearylalkyl dimethylammonium chloride, tridecylalkyl methylammonium chloride, a mixture of methyl (1) tallowalkyl amido ethyl (2) tallowalkyl imidazolinium methyl sulfate (VARISOFT 475) together with coconutalkyl trimethylammonium chloride (ADOGEN 461) in a ratio of VARISOFT to ADOGEN of about 1:1, 3:3, 3:1, 2:3, or 1:3, or a mixture of palmitylalkyl trimethylammonium chloride with coconutalkyl trimethylammonium chloride in a ratio of palmityl to coconut compound of about 3:1, 2:1, 1:1, 1:2,
  • ADOGEN 444 Commercially available as ADOGEN 461.
  • compositions described in Table II are suitable for laundering fabrics soiled with grease or oil using aqueous washing solutions formed from such compositions.
  • compositions having substantially similar greasy/oily soil removal performance properties are realized when in the above compositions the cationic surfactants are replaced with an equivalent amount of decylalkyl trimethylammonium chloride, decylalkyl trimethylammonium hydroxide, C14 alkyl trimethylammonium chloride, distearylalkyl dimethylammonium chloride, tridecylalkyl methylammonium chloride, a mixture of methyl (1) tallowalkyl amido ethyl (2) tallowalkyl imidazolinium methyl sulfate (VARISOFT 475) together with coconutalkyl trimethylammonium chloride (ADOGEN 461) in a ratio of VARISOFT to ADOGEN of about 1:1, 3:3, 3:1, 2:3, or 1:3, or a mixture of palmitylalkyl trimethylammonium chloride with coconutalkyl trimethylammonium chloride in a ratio of palmityl to coconut compound of about 3:1, 2:1, 1:1, 1:2,

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  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
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  • Oil, Petroleum & Natural Gas (AREA)
  • Wood Science & Technology (AREA)
  • Organic Chemistry (AREA)
  • Detergent Compositions (AREA)

Abstract

L'invention concerne des compositions de détergents lessiviels qui sont notamment efficaces pour éliminer les salissures et les tâches de graisse/d'huile sur les tissus pendant le blanchissage. Ces compositions contiennent essentiellement un mélange tensioactif comprenant du sarcosinate d'oléolyle et certains tensioactifs cationiques. Sont également décrits des procédés pour blanchir et pré-traiter des tissus à l'aide de ces compositions.
PCT/US1995/006523 1994-06-01 1995-05-23 Compositions de detergents lessiviels WO1995033033A1 (fr)

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EP95920624A EP0763091A1 (fr) 1994-06-01 1995-05-23 Compositions de detergents lessiviels
MX9606046A MX9606046A (es) 1995-05-23 1995-05-23 Composiciones detergentes para lavanderia.
JP8500999A JPH10501279A (ja) 1994-06-01 1995-05-23 洗濯洗剤組成物

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WO1997043388A2 (fr) * 1996-05-17 1997-11-20 The Procter & Gamble Company Composition detersive
WO1997043365A2 (fr) * 1996-05-17 1997-11-20 The Procter & Gamble Company Composition detersive
US5710295A (en) * 1995-06-06 1998-01-20 Hampshire Chemical Corp. Preparation of alkali metal acyl amino acids
EP0843715A1 (fr) * 1995-07-08 1998-05-27 The Procter & Gamble Company Compositions detergentes
EP0843714A1 (fr) * 1995-07-08 1998-05-27 The Procter & Gamble Company Procede pour laver du linge
EP0856044A1 (fr) * 1995-07-08 1998-08-05 The Procter & Gamble Company Compositions detergentes comprenant un tensio-actif a ester cationique et une enzyme
EP0862607A1 (fr) * 1995-07-08 1998-09-09 The Procter & Gamble Company Compositions detergentes
EP1167617A1 (fr) * 2000-01-19 2002-01-02 Kao Corporation Composition de finition adoucissante
EP0885283B2 (fr) † 1996-02-29 2005-02-16 The Procter & Gamble Company Compositions detergentes liquides pour la lessive, contenant des tensioactifs cationiques et des emulsions a base de silicone
WO2005040321A1 (fr) * 2003-10-07 2005-05-06 Reckitt Benckiser N.V. Combinaison synergique d'agents tensioactifs
US7541472B2 (en) 2004-05-24 2009-06-02 Cropsolution, Inc. 3-Aryl-3-hydroxy-2-methylenepropionic acid esters as fungicides
FR2934153A1 (fr) * 2008-07-23 2010-01-29 Oreal Composition cosmetique comprenant un tensio-actif cationique particulier, un polyol et un polymere epaississant non silicone, utilisation et procede.
JP2016517852A (ja) * 2013-04-20 2016-06-20 クラリアント・インターナシヨナル・リミテツド 油性物質、脂肪酸、アミノ酸界面活性剤、およびｎ−メチル−ｎ−アシルグルカミンを含有する組成物
WO2019105780A1 (fr) * 2017-11-29 2019-06-06 Basf Se Compositions, leur fabrication et leur utilisation
US10772324B2 (en) 2012-11-03 2020-09-15 Clariant International Ltd. Aqueous adjuvant-compositions
US10813862B2 (en) 2012-05-30 2020-10-27 Clariant International Ltd. Use of N-methyl-N-acylglucamines as solubilizers
US10864275B2 (en) 2012-05-30 2020-12-15 Clariant International Ltd. N-methyl-N-acylglucamine-containing composition
US10920080B2 (en) 2015-10-09 2021-02-16 Clariant International Ltd. N-Alkyl glucamine-based universal pigment dispersions
US10961484B2 (en) 2015-10-09 2021-03-30 Clariant International Ltd. Compositions comprising sugar amine and fatty acid
US11220603B2 (en) 2016-05-09 2022-01-11 Clariant International Ltd. Stabilizers for silicate paints
US11425904B2 (en) 2014-04-23 2022-08-30 Clariant International Ltd. Use of aqueous drift-reducing compositions
RU2783163C2 (ru) * 2017-11-29 2022-11-09 Басф Се Стабильные при хранении ферментные препараты, их получение и применение

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JP2018104705A (ja) * 2016-12-27 2018-07-05 花王株式会社 繊維製品用粉末洗浄剤組成物
WO2018124090A1 (fr) * 2016-12-27 2018-07-05 花王株式会社 Composition détergente en poudre pour article textile

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Cited By (39)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5710295A (en) * 1995-06-06 1998-01-20 Hampshire Chemical Corp. Preparation of alkali metal acyl amino acids
EP0843714A1 (fr) * 1995-07-08 1998-05-27 The Procter & Gamble Company Procede pour laver du linge
EP0843714A4 (fr) * 1995-07-08 2000-01-05 Procter & Gamble Procede pour laver du linge
EP0843715A4 (fr) * 1995-07-08 1999-09-29 Procter & Gamble Compositions detergentes
EP0856044A4 (fr) * 1995-07-08 1999-09-29 Procter & Gamble Compositions detergentes comprenant un tensio-actif a ester cationique et une enzyme
EP0862607A4 (fr) * 1995-07-08 1999-08-18 Procter & Gamble Compositions detergentes
EP0862607A1 (fr) * 1995-07-08 1998-09-09 The Procter & Gamble Company Compositions detergentes
EP0856044A1 (fr) * 1995-07-08 1998-08-05 The Procter & Gamble Company Compositions detergentes comprenant un tensio-actif a ester cationique et une enzyme
EP0843715A1 (fr) * 1995-07-08 1998-05-27 The Procter & Gamble Company Compositions detergentes
EP0885283B2 (fr) † 1996-02-29 2005-02-16 The Procter & Gamble Company Compositions detergentes liquides pour la lessive, contenant des tensioactifs cationiques et des emulsions a base de silicone
US6136769A (en) * 1996-05-17 2000-10-24 The Procter & Gamble Company Alkoxylated cationic detergency ingredients
WO1997043387A2 (fr) * 1996-05-17 1997-11-20 The Procter & Gamble Company Composition detersive
WO1997043388A3 (fr) * 1996-05-17 1998-02-12 Procter & Gamble Composition detersive
WO1997043365A3 (fr) * 1996-05-17 1998-01-08 Procter & Gamble Composition detersive
JPH11510554A (ja) * 1996-05-17 1999-09-14 ザ、プロクター、エンド、ギャンブル、カンパニー 洗剤組成物
WO1997044419A3 (fr) * 1996-05-17 1997-12-31 Procter & Gamble Composition detergente
WO1997044419A2 (fr) * 1996-05-17 1997-11-27 The Procter & Gamble Company Composition detergente
WO1997043387A3 (fr) * 1996-05-17 1998-02-19 Procter & Gamble Composition detersive
WO1997043388A2 (fr) * 1996-05-17 1997-11-20 The Procter & Gamble Company Composition detersive
WO1997043365A2 (fr) * 1996-05-17 1997-11-20 The Procter & Gamble Company Composition detersive
EP1167617A4 (fr) * 2000-01-19 2003-05-14 Kao Corp Composition de finition adoucissante
US6596685B2 (en) 2000-01-19 2003-07-22 Kao Corporation Softener composition
EP1167617A1 (fr) * 2000-01-19 2002-01-02 Kao Corporation Composition de finition adoucissante
US7202203B2 (en) 2000-01-19 2007-04-10 Kao Corporation Softener composition
WO2005040321A1 (fr) * 2003-10-07 2005-05-06 Reckitt Benckiser N.V. Combinaison synergique d'agents tensioactifs
US7541472B2 (en) 2004-05-24 2009-06-02 Cropsolution, Inc. 3-Aryl-3-hydroxy-2-methylenepropionic acid esters as fungicides
FR2934153A1 (fr) * 2008-07-23 2010-01-29 Oreal Composition cosmetique comprenant un tensio-actif cationique particulier, un polyol et un polymere epaississant non silicone, utilisation et procede.
US10813862B2 (en) 2012-05-30 2020-10-27 Clariant International Ltd. Use of N-methyl-N-acylglucamines as solubilizers
US10864275B2 (en) 2012-05-30 2020-12-15 Clariant International Ltd. N-methyl-N-acylglucamine-containing composition
US10772324B2 (en) 2012-11-03 2020-09-15 Clariant International Ltd. Aqueous adjuvant-compositions
JP2016517852A (ja) * 2013-04-20 2016-06-20 クラリアント・インターナシヨナル・リミテツド 油性物質、脂肪酸、アミノ酸界面活性剤、およびｎ−メチル−ｎ−アシルグルカミンを含有する組成物
US11425904B2 (en) 2014-04-23 2022-08-30 Clariant International Ltd. Use of aqueous drift-reducing compositions
US10961484B2 (en) 2015-10-09 2021-03-30 Clariant International Ltd. Compositions comprising sugar amine and fatty acid
US10920080B2 (en) 2015-10-09 2021-02-16 Clariant International Ltd. N-Alkyl glucamine-based universal pigment dispersions
US11220603B2 (en) 2016-05-09 2022-01-11 Clariant International Ltd. Stabilizers for silicate paints
WO2019105781A1 (fr) * 2017-11-29 2019-06-06 Basf Se Préparations d'enzyme stables au stockage, leur production et utilisation
WO2019105780A1 (fr) * 2017-11-29 2019-06-06 Basf Se Compositions, leur fabrication et leur utilisation
RU2783163C2 (ru) * 2017-11-29 2022-11-09 Басф Се Стабильные при хранении ферментные препараты, их получение и применение
US11512268B2 (en) 2017-11-29 2022-11-29 Basf Se Storage-stable enzyme preparations, their production and use

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JPH10501279A (ja) 1998-02-03
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