EP0948393A1 - Compositions detergentes contenant des niveaux de concentration faibles de tensioactifs jumeles - Google Patents

Compositions detergentes contenant des niveaux de concentration faibles de tensioactifs jumeles

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Publication number
EP0948393A1
EP0948393A1 EP97942138A EP97942138A EP0948393A1 EP 0948393 A1 EP0948393 A1 EP 0948393A1 EP 97942138 A EP97942138 A EP 97942138A EP 97942138 A EP97942138 A EP 97942138A EP 0948393 A1 EP0948393 A1 EP 0948393A1
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EP
European Patent Office
Prior art keywords
surfactant
alkyl
composition
weight
independently
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Withdrawn
Application number
EP97942138A
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German (de)
English (en)
Inventor
Jiang Yang
Manilal Dahanayake
Gladys Saliba Gabriel
Ronald Brady Bell
David James Tracy
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Solvay USA Inc
Original Assignee
Rhodia Inc
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Application filed by Rhodia Inc filed Critical Rhodia Inc
Publication of EP0948393A1 publication Critical patent/EP0948393A1/fr
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Classifications

    • 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
    • C09K23/18—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
    • 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
    • C09K23/14—Derivatives of phosphoric acid
    • 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
    • C09K23/42—Ethers, e.g. polyglycol ethers of alcohols or phenols
    • 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
    • C11D1/40—Monoamines or polyamines; Salts 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
    • C11D1/38—Cationic compounds
    • C11D1/52—Carboxylic amides, alkylolamides or imides or their condensation products with alkylene oxides
    • C11D1/528—Carboxylic amides (R1-CO-NR2R3), where at least one of the chains R1, R2 or R3 is interrupted by a functional group, e.g. a -NH-, -NR-, -CO-, or -CON- group
    • 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
    • C11D1/722—Ethers of polyoxyalkylene glycols having mixed oxyalkylene groups; Polyalkoxylated fatty alcohols or polyalkoxylated alkylaryl alcohols with mixed oxyalkylele groups

Definitions

  • This invention relates to improved surfactant systems useful as emulsifiers and in detergents at very low concentration.
  • Emulsification is an extremely important technology and it is a process which is used in detergencN .
  • Emulsifiers function as essential ingredients in personal care and household products, industrial and institutional cleaners including shampoo, car washes, carpet shampoo, hand dishwashing liquids, latex foaming and oil recovery compositions: and the like
  • an emulsifier is required to adsorb at an oil-water interface to prevent emulsion ⁇ roplet coalescence
  • the maio ⁇ n of emulsifiers are synthetic surfactants or natural products with amphiphiiic character
  • usage levels of surfactants for effective emulsification are usually above 0.1% active based on the total weight of the detergent solution which is used in the final use composition.
  • gemini surfactant For a given emulsifier system, it would be advantageous to use a lower amount of surfactant to reduce the cost and amount of surfactant waste discharged into the environment: and to improve the performance of final products (e.g.. the film forming and water resistance will be improved in latex paints and skin irritation will be reduced for cosmetic pro ⁇ ucts with less surfactants )
  • conventional surfactants generally have one hydrophilic group and one hydrophobic group
  • Recently a class of compounds having at least two hydrophobic groups and at least two hydrophilic groups have been introduced. These have become known as "gemini surfactants" in the literature (Chemtech. March 1993, pp 30 - 33), and J. American Chemical Soc. 1 5. 10083-10090. (1993) and the references cited therein).
  • Other gemini surfactant compounds that is. compounds having at least two hydrophilic groups and at least two hydrophobic groups are also disclosed in literature but often are not referred to expressly as gemini surfactants.
  • gemini surfactants as emulsifiers. From these studies, it has been found that gemini surfactants are unexpectedly effective emulsifiers when used at very low concentrations in comparison to conventional surfactants. This finding is reflected in superior detergencv at very low concentrations. Other performance properties related to emulsification as mentioned above can be also improved using low concentrations of gemini surfactants.
  • gemini surfactants of the type described and claimed herein can be extremely effective emulsifiers for oil-in-water emulsions at lower concentrations than that needed
  • Figures 1 and 2 are bar graphs representing the comparison of detergencv of polyoxyethylene (13) methylene bis (octylphenol) (MBOP) versus a control of polyoxyethylene (7.5) octylphenol (OP) on different fabrics at 0.005% & 0.01 % by weight respectively.
  • Figures 3 and 4 are bar graphs representing the comparison of detergencv of polyoxyethylene(13) methylene bis (octylphenol) (MBOP) in a 1 : 1 blend with sodium
  • dodecylbenzene sulfonate versus a control of polyoxyethylene (7.5) octylphenol (OP)in a 1 :1 blend with the same sulfonate on various fabrics at 0.001% & 0.005% by weight
  • gemini surfactants is intended to mean surfactants having at least 2 hydrophobic groups and at least 2 hydrophilic groups per molecule.
  • gemini surfactants are reported in the literature, see for example. Okahara et al. J. Japan Oil Chem. Soc. 746 (Yukagaku) (1989); Zhu et al..
  • gemini surfactants are disclosed by U.S. Patent Nos. 2,374.354. Kaplan; 2.524.218, Bersworth; 2.530.147 Bersworth (two hydrophobic tails and three hydrophilic heads); 3.244.724. Gu ⁇ mann; 5,160,450. Okahara. et al., all of which are incorporated herein by reference.
  • the gemini surfactants may be anionic. nonionic. cationic or amphoteric.
  • the hydrophilic and hydrophobic groups of each surfactant moiety (A,A ! ) may be any of those known to be used in conventional surfactants having one hydrophilic group and one hydrophobic group.
  • a typical nonionic gemini surfactant e.g.. a bis-polyoxyethylene alkyl ether
  • Each moiety would contain a hydrophilic group, e.g., polyoxyethylene. and a hydrophobic group, e.g., an alkyl chain.
  • Anionic and nonionic gemini surfactants which are. useful in the present invention include those of the formula: R,
  • R is independently C, to C 2 alkyl.
  • R 4 C(0) -. or R -B-R 5 -
  • R4 is C, to C alkyl.
  • R is C, to C 12 alkyl.
  • B is an amide group.
  • a carboxyl group [ -C(0)-0- ].
  • a carbonyl group, and a polyether group [ -0(EO) a PO) h - ] wherein EO represents ethyleneoxy radicals.
  • PO represents propyleneoxv radicals
  • a and b are numbers of from 0 to 100, a is preferably from about 0 to about 30 and b is preferably from about 0 to 10. wherein a plus b is at least one, and the EO and PO radicals can be randomly mixed or in discrete blocks, and R ⁇ is hydrogen or C ⁇ to C 6
  • R ⁇ is independently hydrogen or C, to C 22 alkyl
  • R 2 is independently a C r C j0 alkyl. -0-. an amide group [ -C(0)N(R 6 )- ]. a polyether group [ -0(EO) a (PO) b - ]. -R 7 -D-R 7 - or
  • R 7 is independently a C, -C 6 alkyl and D is -0-.
  • -S-. an amide group [ -C(0)N(R 6 )- ], or an amino group [ -N ⁇ Rg)- ], wherein ⁇ , , a and b are as defined above, and t is independently 0 or 1.
  • Z is independently hydrogen. -S0 3 Y, -P(0)(OY) 2 . -COOY, -CH 2 COOY, -CH 2 -CH(OH)CH 2 S0 3 Y and when R 2 is not a polyether.
  • Z is also -OS0 3 Y. and - OP(0)(OY) 2 : wherein Y is hydrogen, alkali metal such as sodium and potassium; alkaline earth metal such as magnesium and calcium: ammonium: or organic base salt such as monoethanolamine. diethanolamine. triethanolamine. triethylamine, trimethylamine. N-hydroxyethyl morpholine. and the like.
  • A is independently a straight chain or branched C, to C 6 alkyl.
  • R 3 is a bond, an aryl group such as a
  • phenyl or diphenyl group a C, to C I0 alkyl group, preferably a C, to C 4 alkyl group, most preferably methylene. -0-. -S-, -S-S-. -N(R 6 )-. -R 5 -0-. -R 5 [0(EO) a (PO) b -].
  • alkali * includes substituted alkali, especially the hydroxy substituted derivatives thereof and straight as well as branched chains.
  • Z is hydrogen
  • the gemini surfactants are nonionic.
  • gemini surfactants specifically useful in the present invention include gemini anionic or nonionic surfactants of the formulae:
  • R c represents aryl, preferably phenyl.
  • R 3 . R 4 . Y. Z. a and b are as defined above. More specifically, these compounds comprise:
  • R 4 , R 5 , Z. a. and b are as defined hereinbefore.
  • the primary hydroxyl group of these surfactants can be readih phosphated. sulfated or carboxylated by standard techniques.
  • the compounds included in Formula II can be prepared by a variety of synthetic routes.
  • the compounds of Formula IV can be prepared by condensing a monoalkyl phenol with paraformaldehyde in the presence of an acid catalyst such as acetic acid.
  • the compounds of Formula V can be synthesized by a Lewis acid catalyzed reaction of an alkylphenol with a dicarboxylic acid, e.g., terephthalic acid.
  • a class of gemini surfactants that can be used in providing the improved emulsions which are operable at lower concentrations as disclosed in the present invention include a group of amphote ⁇ c, and cationic quaternan surfactants comprising compounds of the formula VII.
  • R. wherein R. t, and Z are as defined hereinbefore.
  • R is as defined before and includes the [ -(EO) a (PO) b O- ]H moiety.
  • R 2 is as defined before, however, D includes the
  • R 3 is selected from the group consisting of a bond.
  • the compounds of Formula VII comprise:
  • R. R 2 . R . Z. and n are as defined hereinbefore: and m independently equals a number between about 2 and about 10.
  • Representative compounds of Formula VII include.
  • R 9 is independently a C
  • the compounds used in the present invention comprise those of
  • R 3 is a C, - C 4 alkyl. most preferably ethyl.
  • Ro is a lower alkyl of from 1 to about 4 carbon atoms, most preferably methyl: and X is halogen or methylsulfate.
  • the compounds of Formula XIII can be prepared by a variety of snythetic processes.
  • gemini surfactants useful in this invention are those of the formula: R 13 -(CH,) p -N-R 14
  • R, 3 is a sugar moiety, e.g.. a monosaccharide. desaccharide, or polvsaccharide such as glucose: or a polyhydroxy compound such as glycerol; p is independently 0 to 4: R 3 is as defined above in formula VII; and R M is a C r C, 2 alkyl or -C(0)R 4 wherein R 4 is as described above.
  • many of the moieties can be derived from natural sources which will generally contain mixtures of different saturated and unsaturated carbon chain lengths.
  • the natural sources can be illustrated by coconut oil or similar natural oil sources such as palm kernel oil. palm oil. osya oil. rapeseed oil.
  • the fatty acids from natural sources in the form of the fatty acid or the triglyceride oil can be a mixture of alkyl radicals containing from about 5 to about 22 carbon atoms.
  • Illustrative of the natural fatty acids are caprylic (C 8 ). capric (C 10 ). lauric (C,,). myristic (C, 4 ). palmitic (C, 6 ). stearic (C 18 ). oleic (C 18 . monounsaturated). linoleic (C, g , diunsaturated). linolenic (C, 8 . triunsaturated). ricinoleic (C 18 . monounsaturated)
  • These fatty acids can be used per se. as concentrated cuts or as fractionations of natural source acids.
  • the fatty acids with even numbered carbon chain lengths are given as illustrative though the odd numbered fatty acids can also be used.
  • single fatty acids with even numbered carbon chain lengths are given as illustrative though the odd numbered fatty acids can also be used.
  • carboxylic acids e.g.. lauric acid, or other cuts, as suited for the particular application, may be used.
  • the surfactants used in the present invention can be oxyalkylated by reacting the product with an alkylene oxide according to known methods, preferably in the presence of an alkaline catalyst.
  • the free hydroxyl groups of the alkoxylated derivative can then be sulfated.
  • phosphated or acylated using normal methods such as sulfation with sulfamic acid or sulfur trioxide-pyridine complex, or acylation with an acylating agent such as a carboxylic acid, ester, and the naturally occurring triglyceride esters thereof.
  • the surfactant compositions of the invention are extremely effective in aqueous solution at low concentrations as defined herein.
  • the surfactants of the invention can be used in any amount needed for a particular application which can be easily determined by a skilled artisan without undue experimentation.
  • W ile the gemini surfactants of the invention can be used alone, it has been unexpectedly found that blends of the compounds of the invention with certain other conventional well known anionic, nonionic. cationic and amphoteric surfactants provide synergistic effects in relation to critical micelle concentration (cmc) and surface tension reducing ability, and hence improved detergencv.
  • cmc critical micelle concentration
  • Nonionic surfactants including those having an HLB of from 5 to 17. are well known in the detergency art. Examples of such surfactants are listed in U.S. Patent No.
  • Nonlimiting examples of suitable nonionic surfactants which may be used in the present invention are as follows:
  • the polyethylene oxide condensates of alkyl phenols. These compounds include the condensation products of alkyl phenols having an alkyl group containing from about 6 to 12 carbon atoms in either a straight chain or branched chain configuration with ethylene oxide, said ethylene oxide being present in an amount equal to 5 to 25 moles of ethylene oxide per mole of alkyl phenol.
  • the alkyl substituent in such compounds can be derived, for example. from polymerized propylene. diisobutylene. and the like. Examples of
  • nonionic surfactants of this type include Igepal CO-630. marketed by Rhone-Poulenc Inc. and Triton X-45, X-1 14, X- 100, and X-102, all marketed by Union Carbide.
  • the condensation products of aliphatic alcohols with from about 1 to about 25 moles of ethylene oxide can either be straight or branched, primary or secondary, and generally contains from about 8 to about 22 carbon atoms.
  • Examples of such ethoxylated alcohols include the condensation product of myristyl alcohol condensed with about 10 moles of ethylene oxide per mole of alcohol; and the condensation product of about 9
  • Neodol 15-S- 9. marketed by Union Carbide Corporation.
  • Neodol 45-7. and Neodol 45-4. marketed by Shell Chemical Company.
  • the hydrophobic portion of these compounds typically has a molecular weight of from about 1500 to 1800 and exhibits water insolubility.
  • the addition of polyoxyethylene moieties to this hydrophobic portion tends to increase the water solubility of the molecule as a whole, and the liquid character of the product is retained up to the point where the polyoxyethylene content is about 50%) of the total weight of the condensation product, which corresponds to condensation with up to about 40 moles of ethylene oxide.
  • Examples of compounds of this type include certain of the commercially available Pluronic surfactants, marketed by Wyandotte Chemical Corporation.
  • the condensation products of ethylene oxide with the product resulting from the reaction of propylene oxide and e hylenediamine The hydrophobic moiety of these products consists of the reaction product of ethylenediamine and excess propylene oxide, said moiety having a molecular weight of from about 2500 to about 3000.
  • This hydrophobic moiety is condensed with ethylene oxide to the extent that the condensation product contains from about 40% to about 80%) by weight of polyoxyethylene and has a molecular weight of from about 5.000 to about 1 1 ,000.
  • Examples of this type of nonionic surfactant include certain of the commercially available Tetroni ⁇ compounds, marketed by Wyandotte Chemical Corporation.
  • Semi-polar nonionic detergent surfactants include water-soluble amine oxides containing one alkyl moiety of from about 10 to 18 carbon atoms and 2
  • moieties selected from the group consisting of alkyl groups and hydroxyalkyl groups containing from 1 to about 3 carbon atoms water-soluble phosphine oxides containing one alkyl moiety of about 10 to 18 carbon atoms and 2 moieties selected from the group consisting of alkyl groups and hydroxyalkyl groups containing from about 1 to 3 carbons atoms: and water-soluble sulfoxides containing one alkyl moiety of from about 10 to 18 carbon atoms and a moiety selected from the group consisting of alkyl and hydroxyalkyl moieties of from about 1 to 3 carbon atoms.
  • Preferred semi-polar nonionic detergent surfactants are the amine oxide
  • detergent surfactants having the formula:
  • R 1 is an alkyl, hydroxy alkyl, or alkyl phenyl group or mixtures thereof containing from about 8 to about 22 carbon atoms.
  • R is an alkylene or hydroxy alkylene group containing from 2 to 3 carbon atoms or mixtures thereof, x is from 0 to about 3 and each R is an alkyl or hydroxy alkyl group containing from 1 to about 3 carbon atoms or a_polyethylene oxide group containing from one to about 3 ethylene oxide groups and said R groups can be attached to each other, e.g.. through an oxygen or nitrogen atom to form a ring structure.
  • Preferred amine oxide detergent surfactants are C ] 0 -Cj 8 alkyl dimethyl amine oxide.
  • Nonionic detergent surfactants ( l )-(4) are conventional ethoxylated nonionic detergent surfactants and mixtures thereof can be used.
  • Preferred alcohol ethoxylate nonionic surfactants for use in the compositions of the liquid, powder, and gel applications are biodegradable and have the formula R(OC,H 4 ) n OH wherein R is a primary or secondary alkyl chain of from about 8 to about 22. preferably from about 10 to about 20 carbon atoms and n is an average of from about 2 to about 12. particularly from about 2 to about 9.
  • the nonionics have an HLB (hydrophilic-lipophilic balance) of from about 5 to about 17. preferably from about 6 about 15 HLB is defined in detail in Nonionic Surfactants, by M J Schick. Marcel Dekker. Inc., 1966, pages 606-613. incorporated herein by reference In preferred
  • n is from 3 to 7
  • Primary linear alcohol ethoxvlates e.g , alcohol ethoxylates produced from organic alcohols which contain about 20% > 2-methyl branched isomers, commercially available from Shell Chemical Company under the trademark Neodol
  • Neodol are preferred from a performance standpoint
  • nonionic surfactants are preferably solids at room temperature with a melting point above about 25° C , preferabh above about 30° C Bar compositions of the present invention made with lower melting nonionic surfactants are generally too soft, not meeting the bar firmness requirements of the present invention.
  • nonionic surfactants usable herein, but not limited to bar applications, include fatty acid glycerine and polyglycerine esters, sorbitan sucrose fatty acid esters, polyoxyethylene alkyl and alkyl allyl ethers, polyoxyethylene lanolin alcohol, glycerine and polyoxyethylene glycerine fatty acid esters, polyoxyethylene propylene glycol and sorbitol fatty acid esters, polyoxyethylene lanolin, castor oil or hardened castor oil derivatives, polyoxyethylene fatty acid amides, polyoxyethylene alkyl amines, alkylpyrrolidone, glucamides, alkylpolyglucosides. and mono- and dialkanol amides.
  • Typical fatty acid glycerine and polyglycerine esters as well as typical sorbitan sucrose fatty acid esters, fatty acid amides, and polyethylene oxide/polypropylene oxide block copolvmers are disclosed by U.S. Patent No. 5.510.042. Hartman et al. incorporated herein by reference.
  • the castor oil derivatives are typically ethoxylated castor oil. It is noted that other ethoxylated natural fats, oils or waxes are also suitable.
  • Polyoxyethylene fatty acid amides are made by ethoxylation of fatty acid amides with one or two moles of ethylene oxide or by condensing mono-or diethanol amines with fatty acid.
  • Polyoxyethylene alkyl amines include those of formula: RNH-(CH,CH,0) n -H. wherein R is C 6 to C,, alkyl and n is from 1 to about 100.
  • Monoalkanol amides include those of formula: RCONHR'OH. wherein R is C 6 -C 2 alkyl and R is C, to C 6 alkylene.
  • Dialkanol amides are typically mixtures of: diethanolamide: RCON(CH,CH,OH) 2 ; amide ester: RCON(CH,CH,OH)-CH,CH,OOCR; amine ester: RCOOCH,CH,NHCH,CH,OH; and amine soap: RCOOH,N(CH,CH,OH) 2 , wherein R in the above formulas is an alkyl of from 6 to 22 carbon atoms.
  • Examples of preferred but not limiting surfactants for detergent bar products are the following:
  • deca-, undeca-. dodeca-, tetradeca-. and pentadeca-ethoxylates of n- hexadecanol. and n-hexadecanol. and n-octadecanol having an HLB within the range recited herein are useful nonionics in the context of this -invention.
  • Exemplary ethoxylated primary alcohols useful herein as the conventional nonionic surfactants of the compositions are n-C 18 EO(10): n-C 14 EO(13): and n-C 10 EO( l 1 ).
  • the ethoxvlates of mixed natural or synthetic alcohols in the "tallow ** chain length range are also useful herein.
  • Specific examples of such materials include tallow-alcohol-EO(l 1 ).
  • Exemplary ethoxylated secondary alcohols useful herein are 2- C l EO(l 1); 2-C 20 EO(l 1 ): and 2-C 16 EOf 14).
  • the hexa- through octadeca- ethoxylates of alkylated phenols, particularly monohyd ⁇ c alkylphenols. having an HLB within the range recited herein are useful as conventional nonionic surfactants in the instant compositions
  • ethoxylated alkylphenols useful in the mixtures herein are p-t ⁇ dec> Iphenol EO(l l ) and p- pentadecylphenol EO(18) Especially preferred is Nonyl Nonoxynol-49 known as Igepal* DM-880 from Rhone-Poulenc Inc
  • a phenylene group in the nonionic formula is the equivalent of an alkylene group containing from 2 to 4 carbon atoms
  • nonionics containing a phenylene group are considered to contain an equivalent number of carbon atoms calculated as the sum of the carbon atoms in the alkyl group plus about 3 3 carbon atoms for each phenvlene group Olefinic Alkoxylates
  • alkenyl alcohols both p ⁇ man and seconda ⁇ and alkenvl phenols corresponding to those disclosed immediately here ⁇ nabo ⁇ e can be ethoxylated to an HLB within the range recited herein and used as the conventional nonionic surfactants of the instant compositions
  • Branched chain primary and seconda alcohols which are available can be ethoxylated and employed as conventional nonionic surfactants in compositions herein
  • the above ethoxylated nonionic surfactants are useful in the present compositions alone or in combination, and the term "nonionic surfactant" encompasses mixed nonionic surface active agents.
  • nonionic surfactants of this invention include alkylpolysaccharides, preferably alkylpolyglucosides of the formula:
  • R is a hydrophobic group selected from the group consisting of a C
  • compositions of the present invention can also comprise mixtures of the above nonionic surfactants.
  • Anionic surfactants include any of the known hydrophobes attached to a carboxylate. sulfonate.
  • Salts may be the sodium, potassium, ammonium and amine salts of such surfactants
  • Useful anionic surfactants can be organic sulfunc reaction products having in their molecular structure an alkyl group containing from about 8 to about 22 carbon atoms and a sulfomc acid or sulfunc acid ester group, or mixtures thereof (Included in the
  • alkyl is the alkyl portion of acyl groups )
  • alkyl sulfates especially those obtained by sulfating the higher alcohols (C 8 -C l g carbon atoms) produced from the glyce ⁇ des of tallow or coconut oil.
  • alkyl benzene sulfonates are the alkyl sulfates. especially those obtained by sulfating the higher alcohols (C 8 -C l g carbon atoms) produced from the glyce ⁇ des of tallow or coconut oil.
  • esters of alpha-sulfonated fatty acids preferably containing from about 6 to 20 carbon atoms in the ester group
  • 2- acvloxvalkane-1 -sulfomc acids preferably containing from about 2 to 9 carbon atoms in the ac ⁇ l group and from about 9 to about 23 carbon atoms in the alkane moiety
  • alkyl ether sulfates preferably containing from about 10 to 20 carbon atoms in the alkyl group and from about 1 to 30 moles of ethylene oxide, olefin sulfonates preferabh containing from about 12 to 24 carbon atoms, and beta-alkvloxv alkane sulfonates preferably containing from about 1 to 3 carbon atoms in the alkyl group and from about 8 to 20 carbon atoms in the alkane moiety
  • Anionic surfactants based on the higher fatty acids, l e ' soaps "" are useful anionic surfactants herein Higher fatn acids containing from about 8 to about 24 carbon atoms and preferably from about 10 to about 20 carbon atoms and the coconut and tallow soaps can also be used herein as corrosion inhibitors
  • Preferred water-soluble anionic organic surfactants herein include linear alkyl benzene sulfonates containing from about 10 to about 18 carbon atoms in the alkyl group; branched alkyl benzene sulfonates containing from about 10 to about 18 carbon
  • alkyl group atoms in the alkyl group; the tallow range alkyl sulfates; the coconut range alkyl glyceryl sulfonates; alkyl ether (ethoxylated) sulfates wherein the alkyl moiety contains from about 12 to 18 carbon atoms and wherein the average degree of ethoxylation varies between " 1 and 12. especially 3 to 9; the sulfated condensation products of tallow alcohol with from about 3 to 12, especially 6 to 9. moles of ethylene oxide: and olefin sulfonates containing from about 14 to 16 carbon atoms.
  • Specific preferred anionics for use herein include: the linear C !
  • LAS 0 -C M alkvl benzene sulfonates
  • ABS branched C ]0 -C ]4 alkyl benzene sulfonates
  • tallow alkyl " sulfates the coconut alkyl glyceryl ether sulfonates
  • commercial grades of the surfactants can contain non-interfering components which are processing by-products.
  • commercial alkaryl sulfonates preferably C 10 -C 14
  • anionic surfactants used herein include fatty acid soaps,
  • ether carboxylic acids and salts thereof alkane sulfonate salts, ⁇ -olefin sulfonate salts. sulfonate salts of higher fatty acid esters, higher alcohol sulfate ester or ether ester
  • alkyl preferably higher alcohol phosphate ester and ether ester salts, and condensates of higher fatty acids and amino acids.
  • Fatty acid soaps include those having the formula: R-C(0)OM, wherein R is C 6 to C 22 alkyl and M is preferably sodium.
  • Salts of ether carboxylic acids and salts thereof include those having the formula: R-(OR') n -OCH,C(0)OM. wherein R is C 6 to C,, alkyl. R 1 is C, to C, 0 , preferably C, alkyl. and M is preferably sodium.
  • Alkane sulfonate salts and ⁇ -olefin sulfonate salts have the formula: R- S0 3 M. wherein R is C 6 to C 2 alkyl or ⁇ -olefin. respectively, and M is preferably
  • Sulfonate salts of higher fatty acid esters include those having the formula:
  • R is C I2 to C 22 alkyl
  • R is C ⁇ to C 18 alkyl
  • M is preferably sodium.
  • Higher alcohol sulfate ester salts include those having the formula:
  • R is C,,-C,, alkyl.
  • R is C,-C 18 hydroxyalkyl.
  • M is preferably sodium.
  • Higher alcohol sulfate ether ester salts include those having the formula: RC(0)(OCH,CH,) X -R' -OS0 3 M. wherein R is C 12 -C, 2 alkyl. R is C r C 18 hydroxyalkyl. M is preferably sodium and x is
  • Higher alcohol phosphate ester and ether ester salts include compounds of the
  • R-(OR l ) n -0) 3 -PO wherein R is alkyl or hydroxyalkyl of 12 to 22 carbon atoms, R 1 is C 2 H 4 , n is an integer from 5 to 25. and M is preferably sodium.
  • anionic surfactants herein are sodium coconut oil fatty acid monoglyceride sulfonates and sulfates; sodium or potassium salts of alkyl phenol ethylene oxide ether sulfates containing from about 1 to about 10 units of ethylene oxide per molecule and wherein the alkyl groups contain from about 8 to about 12 carbon atoms; and sodium or potassium salts of alkyl ethylene oxide ether sulfates containing about 1 to about 10 units of ethylene oxide per molecule and wherein the alkyl group contains from about 10 to about 20 carbon atoms.
  • C. Cationic Surfactants Preferred cationic surfactants of the present invention are the reaction products of higher fatty acids with a polyamine selected from the group consisting of hydroxyalkylalkylenediamines and dialkylenetriamines and mixtures thereof.
  • a preferred component is a nitrogenous compound selected from the group consisting of:
  • said reaction product containing a composition having a compound of the formula:
  • R is an acyclic aliphatic C ! 5 -C 21 hydrocarbon group and R, and R 3 are divalent C
  • Another preferred component is a cationic nitrogenous salt containing one long chain acyclic aliphatic C ⁇ -C,, hydrocarbon group selected from the group consisting of
  • R is an acyclic aliphatic C ⁇ -C,, Hydrocarbon group.
  • R ⁇ and R ⁇ are C r C 4 saturated alky l or hydroxyalkyl groups, and A [-] is an anion. especially as described in more detail hereinafter, examples of these surfactants are sold by Witco Chemical Company under the Adogen trademarks; (ii) substituted imidazolinium salts having the formula:
  • R is an acyclic aliphatic C 15 -C 21 hydrocarbon group
  • R 7 is a hydrogen or a C C 4 saturated alkyl or hydroxyalkyl group
  • a [-] is an anion
  • R is a C r C 3 alkyl group and R,.
  • R and A [-] are as defined above; an example of which is commercially available under the Monaquat ISIES trademark from Mona Industries. Inc.: (iv) alkylpyridihium salts having the formula:
  • R is an acyclic aliphatic C I 6 -C 22 hydrocarbon group and A [-] is an anion; and (v) alkanamide alkylene pyridinium salts having the formula: wherein R, is an acyclic aliphatic C ⁇ -C,, hydrocarbon group, R, is a divalent C,-C 3 alkylene group, and A [-] is an ion group; and mixtures thereof.
  • 5 -C 2 , hydrocarbon groups or one said group and an arylalkyl group are selected from the group consisting of:
  • each R 4 is an acyclic aliphatic C, 5 -C,, hydrocarbon group.
  • R is a C r C 4 saturated alkyl or hydroxyalkyl group.
  • R g is selected from the group consisting of R 4 and R 5 groups, and
  • a [-] is an anion defined as above; examples of which are commercially available from Witco Company under the Adogen trademarks: (ii) diamido quaternary ammonium salts having the formula: O R, O
  • each R is an acyclic aliphatic C 1 -C 2) hydrocarbon group
  • R is a divalent alkylene group having 1 to 3 "carbon atoms.
  • R 5 and Rg are C,-C 4 saturated alkyl or hydroxyalkyl groups, and
  • a [-] is an anion; examples of which are sold by Witco Chemical Company under the Varisoft trademark; (iii) diamino alkoxylated quaternary ammonium salts having the formula:
  • n is equal to 1 to about 5. and R,. R,. R 5 and A [-] are as defined above;
  • each R is an acyclic aliphatic C I 5 -C 2 , hydrocarbon group, each R 5 is a C
  • each R ⁇ s an acyclic aliphatic C, ⁇ -C 1 hydrocarbon group.
  • R is a divalent alkylene group having 1 to 3 carbon atoms, and R, and A [-] are as defined above, examples are commercially available from Witco Chemical Company under the Varisoft 475 and Varisoft 445 trademarks, and (vi) substituted imidazolinium salts having the formula
  • the more preferred cationic conventional surfactant is selected from the group consisting of an alkyltnmethylammonium salt, a dialkyldimethylammonium salt, an alkyldimethylbenzylammonium salt, an alkylpy ⁇ dinium salt, an alkylisoquinohnium salt, benzethonium chloride, and an acylamino acid cationic surfactant
  • the anion A [-] provides electrical neutrality
  • the anion used to provide electrical neutrality in these salts is a hahde. such as chlonde. bromide, or iodide
  • other anions can be used, such as methylsulfate. ethylsulfate. acetate, formate, sulfate. carbonate, and the like Chloride and methylsulfate are preferred herein as anion A
  • Cationic surfactants are commonh employed as fabric softeners in
  • imidazolinium salts have been used by themselves or in combination with other agents in the treatment of fabrics as disclosed by U.S. Patent No. 4.127.489. Pracht. et al.. incorporated herein by reference in its entirety.
  • U.S. Patent No. 2,874.074. Johnson discloses using imidazolinium salts to condition fabrics; and U.S. Patent No.3.681,241. Rudy, and U.S. Patent No. 3,033.704, Sherrill et al. disclose
  • Amphoteric Surfactants have a positive or negative charge or both on the
  • hydrophilic part of the molecule in acidic or alkaline media hydrophilic part of the molecule in acidic or alkaline media.
  • amphoteric surfactants examples include:
  • amphoteric surfactants include the alkali metal, alkaline earth metal, ammonium or substituted ammonium salts of alkyl amphocarboxyglycinates and alkyl amphocarboxypropionates. alkyl amphodipropionates. alkyl amphodiacetates. alkyl amphoglycinates and alkyl amphopropionates wherein alkyl represents an alkyl group having 6 to 20 carbon atoms.
  • suitable amphoteric surfactants include alkyliminopropionates.
  • alkyl iminodipropionates and alkyl amphopropylsulfonates having between 12 and 18 carbon atoms
  • alkylbetaines and amidopropylbetaines and alkylsultaines and alkylamidopropylhydroxy sultaines wherein alkyl represents an alkyl group having 6 to 20 carbon atoms are especially preferred.
  • amphoteric surfactants include both mono and dicarboxvlates such as those of the formulae:
  • R is an alkyl group of 6-20 carbon atoms
  • x is 1 or 2
  • M is hydrogen or sodium. Mixtures of the above structures are particularly preferred.
  • amphoteric surfactants include the following: Alkyl betaines
  • R is an alkyl group of 6-20 carbon atoms and M is hydrogen or sodium.
  • amphoteric surfactants particularly preferred are the alkali salts of alkyl amphocarboxyglycinates and alkyl amphocarboxypropionates. alk> 1 amphodipropionates. alkyl amphodiacetates. alkyl amphoglycinates. alky 1 amphopropyl sulfonates and alkyl amphopropionates wherein alkyl represents an 1 group having 6 to 20 carbon atoms. Even more preferred are compounds wherein the alkyl group is derived from coconut oil or is a lauryl group, for example, cocoamphodipropionate. Such cocoamphodipropionate surfactants are commercially sold under the trademarks Miranol C2M-SF CONC. and Miranol FBS by Rhone -
  • Poulenc Inc. and include:
  • cocoamphoacetate (sold under the trademarks MIRANOL CM CONC. and MIRAPON FA), cocoamphopropionate (sold under the trademarks MIRANOL CM-SF CONC. and MIRAPON FAS).
  • cocoamphodiacetate (sold under the trademarks MIRANOL C2M CONC. and MIRAPON FB), lauroamphoacetate (sold under the trademarks MIRANOL HM CONC. and MIRAPON LA), lauroamphodiacetate (sold under the trademarks MIRANOL H2M CONC. and MIRAPON LB), lauroamphodipropionate (sold under the trademarks MIRANOL H2M SF CONC. AND MIRAPON LBS).
  • lauroamphodiacetate obtained from a mixture of lauric and myristic acids (sold under the trademark MIRANOL BM CONC). and cocoamphopropyl sulfonate (sold under the trademark MIRANOL CS CONC.)
  • caproamphoacetate sold under the trademark MIRANOL SM CONC.
  • stearoamphoacetate sold under the trademark MIRANOL DM.
  • the aqueous surfactant compositions of the invention comprise a concentration of surfactant equal to or less than the cmc of corresponding conventional surfactants assuming that the gemini is represented in the conventional surfactants as a surfactant having only one hydrophobic grouping and one hydrophilic grouping corresponding to those in the gemini surfactant.
  • the total surfactant loading is equal to or less than 80% and more preferably equal to or-less than 60% of the cmc of the conventional surfactants in the final use area.
  • the total aqueous surfactant concentration at end-use level is less than or equal to about 0.01 % total surfactant on an active basis, preferably less than about or equal to 0.008%.
  • gemini surfactant ranges from 100% to about 10%. preferably from 100% to about 20% and more preferably from 100% to about 35% of the total active surfactant in the end-use compositions.
  • the remainder of the surfactant actives comprise other surfactants not claimed under the term "gemini surfactants" including conventional and other
  • surfactant compositions comprising: 1 ) from about 10% to about 100% by weight of nonionic. cationic. anionic. or amphoteric gemini surfactants or a combination thereof : and
  • Detergent compositions prepared utilizing the instant surfactant compositions can be used in laundering processes by forming dilute aqueous solutions of the detergent compositions containing said surfactant compositions and agitating same with soiled fabrics.
  • the surfactant compositions of the instant invention can be used in detergent compositions at from about 0.5% to about 80%, preferably from about 2% to about 50% by weight. based on the total weight of the detergent composition.
  • auxiliary additives e.g.. inorganic salts such as Glauber salt and common salt, builders, humectants. solubilizing agents. UV absorbers, pH adjusting agents, softeners, soil release polymers, soil anti-redeposition agents, conditioning polymers (cationic) for hair and fabric softening, chelating agents, and viscosity modifiers may be added to the surfactant compositions of the invention to form the detergent compositions as the ultimate end-use aqueous surfactant/composition requires.
  • auxiliary additives e.g... inorganic salts such as Glauber salt and common salt, builders, humectants. solubilizing agents.
  • UV absorbers, pH adjusting agents, softeners, soil release polymers, soil anti-redeposition agents, conditioning polymers (cationic) for hair and fabric softening, chelating agents, and viscosity modifiers may be added to the surfactant compositions of the invention to form the detergent compositions as the ultimate end-use aque
  • Such detergent compositions provide excellent detergency at very low surfactant use concentrations, and can be formulated to provide different sudsing patterns by varying the amounts and types of the gemini surfactants used and the nature of the other anionic and nonionic surfactants present.
  • the gemini surfactants of the invention are extremely mild and non-irritating to both eyes and skin and exhibit low toxicity; enhanced wetting speed, greater surface tension reduction, low and high foaming profile depending on the gemini used, and foam stabilization properties. They also provide excellent compatibility with other surfactants.
  • the products of the invention are stable over a wide pH range and are biodegradable. These properties make these surfactants adaptable for use in products ranging from cosmetics to industrial applications, such as for non-irritating shampoos, e.g., baby shampoos, body shampoos, bubble baths, bath gels, hair conditioning gels, lotions, skin creams, make up removal creams, detergents, fabric softeners and other washing and cosmetic products that contact the skin.
  • the surfactants of the invention can also find use as hard surface cleaners including cars, dishes, toilets, floors, and the like; laundry detergents and soaps; metal working aids; and the like.
  • Oil-in-water emulsions are prepared using the following formulation of 10% mineral oil. about 90% water and 0.01 % surfactant active (based on water phase).
  • the coarse emulsions are prepared by vortex mixing each composition for 30 seconds.
  • Each emulsion is characterized by droplet size using an optical microscope, the smaller average droplet size indicating a greater degree of emulsification. Stability is determined by the degree of separation of oil at 23°C respectively, the lower the
  • EXAMPLE 3 The oil-in-water emulsions are prepared using a formulation of 65% mineral oil. about 35% water and 0.028% surfactant active (based on water). The emulsions are prepared by blending in a rotor-stator type mixer (2000 rpm) for 3 min. Emulsions are characterized by droplet size using an optical microscope and stability by degree of separation of oil at 23 °C respectively. The results are reported in Table 3 as follows:
  • Amphoteric and cationic gemini surfactants are used as emulsifiers for mineral oil and compared to corresponding conventional surfactants. The results are shown in Table 4.
  • Table 7 shows the detergency with dust-sebum It can be seen that gemini surfactant shows no significant advantage over the traditional surfactants at 0.02% surfactant use concentration, and especially lower performance on polyester fabric. However, gemini surfactants compositions of the invention show a significant advantage over the traditional detergent blend on dust-sebum cotton detergency at 0.01%) usage levels, and this trend is more obvious at the even lower level, 0.005%.
  • the gemini surfactant can be also blended with conventional anionic and nonionic surfactants to enhance the detergency of the mixture.
  • the surfactants compared are a 3/3/2 ratio blend of polyoxyethylene (7.5) octylphenol (OP), sodium dodecylbenzene sulfonate (LAS), and polyoxyethylene ( 13) methylene bis(octylphenol) (MBOP). This enhanced performance is shown in Table 10, in which the total surfactant content is kept at 0.005%.
  • the wash condition is: 150 ppm hard water. 57 ppm triethanolamine/ monoethanolamine (1/1 ) and 37.8°C

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Abstract

L'invention concerne des compositions aqueuses à base de tensioactifs contenant de faibles concentrations de matières actives de tensioactifs, comprenant un mélange de tensioactifs présentant un ou plusieurs tensioactifs jumelés. La composition aqueuse contient une quantité totale de tensioactif basée sur un poids de matières actives égale ou inférieure à 0,01 % en poids sur la base du poids total de la composition. Les tensioactifs jumelés comprennent environ 10 % à environ 100 % en poids du poids total des matières actives de tensioactifs dans une composition aqueuse.
EP97942138A 1996-10-04 1997-10-06 Compositions detergentes contenant des niveaux de concentration faibles de tensioactifs jumeles Withdrawn EP0948393A1 (fr)

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DE19724897A1 (de) * 1997-06-12 1998-12-17 Henkel Kgaa Tensidgemisch und Reinigungsmittel mit Gemini-Tensiden
AU740437B2 (en) 1998-04-22 2001-11-01 Hercules Incorporated Paper size dispersions
CN106606992A (zh) * 2015-10-21 2017-05-03 南京理工大学 非对称型双子咪唑表面活性剂及其制备方法
CN106497703A (zh) * 2016-10-31 2017-03-15 佛山市南海东方澳龙制药有限公司 一种养殖场用含双子表面活性剂的清洗剂及其制备方法
US20210163813A1 (en) * 2017-12-18 2021-06-03 Dow Global Technologies Llc Ethyleneamine sulfonate-based surfactant for high temperature foaming
CA3132641A1 (fr) 2019-03-06 2020-09-10 Greentech Global Pte. Ltd. Dispersions liquides pour halogenures d'acyle
CN110523539A (zh) * 2019-08-14 2019-12-03 江西理工大学 一种新型表面活性剂在铝土矿反浮选上的应用方法
CA3166630A1 (fr) 2020-01-03 2021-07-08 Berg Llc Amides polycycliques utilises en tant que modulateurs d'ube2k pour le traitement du cancer

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DE3104991A1 (de) * 1981-02-12 1982-08-19 Hoechst Ag, 6000 Frankfurt Anionische grenzflaechenaktive verbindungen auf basis oxalkylierter naphthol-novolake und deren verwendung
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DE4441363A1 (de) * 1994-11-21 1996-05-23 Huels Chemische Werke Ag Amphiphile Verbindungen mit mindestens zwei hydrophilen und mindestens zwei hydrophoben Gruppen auf Basis von Di-, Oligo- oder Polyolethern
DE19505368A1 (de) * 1995-02-17 1996-08-22 Huels Chemische Werke Ag Amphiphile Verbindungen mit mindestens zwei hydrophilen und mindestens zwei hydrophoben Gruppen auf der Basis von Dicarbonsäurediamiden

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