US3501409A - Detergent-hydrotrope composition - Google Patents

Detergent-hydrotrope composition Download PDF

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Publication number
US3501409A
US3501409A US652017A US3501409DA US3501409A US 3501409 A US3501409 A US 3501409A US 652017 A US652017 A US 652017A US 3501409D A US3501409D A US 3501409DA US 3501409 A US3501409 A US 3501409A
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United States
Prior art keywords
detergent
sulfate
sulfonate
liquid
carbon atoms
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.)
Expired - Lifetime
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US652017A
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English (en)
Inventor
Ted P Matson
Henry T Watanabe
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.)
Vista Chemical Co
ConocoPhillips Co
Original Assignee
Continental Oil Co
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Publication of US3501409A publication Critical patent/US3501409A/en
Assigned to VISTA CHEMICAL COMPANY reassignment VISTA CHEMICAL COMPANY ASSIGNMENT OF ASSIGNORS INTEREST. Assignors: CONOCO INC.
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
    • C11D1/02—Anionic compounds
    • C11D1/37—Mixtures of compounds all of which are anionic
    • 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
    • C11D1/523—Carboxylic alkylolamides, or dialkylolamides, or hydroxycarboxylic amides (R1-CO-NR2R3), where R1, R2 or R3 contain one hydroxy group per alkyl 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
    • C11D1/38—Cationic compounds
    • C11D1/65—Mixtures of anionic with cationic compounds
    • C11D1/655—Mixtures of sulfonated products with alkylolamides of carboxylic acids
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
    • C11D3/16—Organic compounds
    • C11D3/34—Organic compounds containing sulfur
    • C11D3/3409—Alkyl -, alkenyl -, cycloalkyl - or terpene sulfates or sulfonates
    • 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

Definitions

  • This invention relates to fluid detergent compositions of the alkylbenzene sulfonate type, and particularly to slurry compositions and liquid compositions.
  • Liquid detergents both light duty and heavy duty, have problems with clarity because the washing effec* tiveness needs push the detergent content towards the saturation point at normal temperatures. Hydrotropes are used with these compositions to increase the solubility of the alkylbenzene sulfonate detergents and thereby lower the cloud point of the composition.
  • An object of the invention is a slurry detergent composition which has a lower viscosity at a given alkylbenzene sulfonate and water content than conventional compositions; or has a higher alkylbenzene sulfonate content at a given viscosity than conventional compositions.
  • a particular object of the invention is an alkylbenzene sulfonate liquid, light-duty detergent having a low cloud point.
  • a further object is an alkylbenzene sulfonate liquid, heavy-duty detergent having a low cloud point.
  • the invention encompasses a fluid detergent composition consisting essentially of (a) water-soluble alkylbenzene sulfonate having about 816 alkyl carbon atoms; (b) alkylethoxy sulfate, having 4-10 alkyl carbon atoms, and about 15-55% of ethylene oxide units, in an amount at least suflicient to increase the water solubility of said sulfonate; and (0) liquid water, in a major proportion.
  • the invention encompasses a slurry detergent composition consisting essentially of (a) Water soluble alkylbenzene sulfonate having about 8-16 alkyl carbon atoms in an amount of about 30 to 50%; (b) 91- kylethoxy sulfate, having 4-10 alkyl carbon atoms, and about 15-55% of ethylene oxide units, in an amount of about 2-10% based on said composition; and (c) the remainder liquid water in an amount suflicient to afford a pasty slurry composition.
  • the invention encompasses a liquid, light-duty detergent composition including (a) alkylbenzene sulfonate having about 8-16 alkyl carbon atoms, about 18-32%; (h) alkylethoxy sulfate, having 4-10 alkyl carbon atoms and about 15-55% of ethylene oxide units, in an amount of about 515%, and (c) at least one member of the class consisting of: 1) foam stabilizer, (2.) ethoxy nonionic detergent, and (3) alkylethoxy sulfate detergent having at least about 12 alkyl carbon atoms, wherein said stabilizer, if present, is present in an amount of about 2-10% and said detergent, if present, is present in a total of about 10-25%; and (d) liquid water, as essentially the remainder.
  • the invention encompasses a liquid, heavy-duty detergent composition including (a) alkylbenzene sulfonate having about 846' alkyl carbon atoms, about 13 to 25%; (b) a potassium polyphosphate compound, about 10 to 30%; (c) alkylethoxy sulfate, having 4-10 alkyl carbon atoms and about 15-55 of ethylene oxide units, in an amount of about 545%; and (d) similarly to the light-duty formulation above, a foam stabilizer, an ethoxy nonionic detergent or an alkylethoxy sulfate detergent.
  • the molecular weight of the alkylbenzene sulfonate constituent used in heavy-duty formulations may be slightly higher than that used in light-duty formulations.
  • linear alkylbenzene sulfonate detergent compositions are surprisingly more responsive to the alkylethoxy sulfate hydrotrope than the highly branched alkylbenzene sulfonates, such as propylene tetramer benzene sulfonate.
  • the invention is directed to fluid detergents composition which includes the very viscous paste or cold creamy types commonly called detergent slurry and the low viscosity compositions commonly called liquid light-duty and liquid heavy-duty detergentsthese are true solutions.
  • liquid water is present in a major proportion; in the light-duty liquid detergent compositions, the water'normally forms more than 50% of the composition; whereas in the heavy-duty liquid compositions, the water content is less than but in the neighborhood of 50%.
  • the amount of water present in slurry compositions is dependent on the viscosity desired and the hydrotrope content, but is usually on the order of the sulfonate content. Always the water and the sulfonate detergent are the major components of the fluid detergents of the invention.
  • the detergent compositions of the invention may be classified as a water-soluble alkylbenzene sulfonate type.
  • alkyl carbon atoms total about 8-16, commonly 12-14.
  • ABS highly branched alkylbenzene sulfonates
  • LES linear alkylbenzene sulfonates
  • Illustrative of the ABS type are those derived from benzene and butylene trimer and propylene 3 tetramer.
  • Illustrative of the linear ABS type are those derived from benzene and monochloro-straight chain hydrocarbons, such a monochlorododecane.
  • the linear alkylbenzene sulfonates are preferred.
  • the amount of defined sulfonate present will be dependent on the fluid composition wanted. In the case of light-duty liquid detergents, about 18-32% will generally be defined sulfonate. In the case of heavy-duty liquid detergents, about 13-25% Will generally be defined sulfonate. (Herein all percentages are weight percent and are based on the total detergent composition.)
  • the detergent composition of the invention includes a water-soluble alkylethoxy sulfate as a hydrotrope.
  • This alkylethoxy sulfate may be depicted: R(OC H 050 M where R is an alkyl group having 4-10 carbon atoms with from 4-8 carbon atoms being preferred, it is equal to at least 1 and M may be any ion or radical conventionally known in the detergent art in connection with water-soluble detergent sulfates.
  • R may be branched or straight-chain, although a straight chain (n-alkyl) is preferred.
  • the alkylethoxy sulfate includes at least about 1 ethylene oxide unit.
  • ethylene oxide unit content may be used in the composition of the invention.
  • ethylene oxide content of the hydrotrope here is defined according to another convention of the art, namely, weight percent of ethylene oxide units present based on the ether alcohol intermediate.
  • the alkylethoxy sulfate hydrotrope here contains between about 15 and 55% of ethylene oxide units.
  • the alkylethoxy sulfate hydrotrope may include only one alkyl species or it may include more than one species as where the ether alcohol is prepared from a mixture of alkanols, for example, ALFOL 610 alcohols (trade name of Continental Oil Company) which contains n-alkanols of 6 carbon atoms 21% by weight, 8 carbon atoms 36% and 10 carbon atoms 43%. With such mixtures it is preferred that at least half of the species be of the 6 or 8 carbon atom variety.
  • ALFOL 610 alcohols trade name of Continental Oil Company
  • Sufficient alkylethoxy sulfate hydrotrope is present in the fluid detergent composition to increase the water solubility of the defined sulfonate detergent. Commonly, this is observed as a decrease in viscosity of a slurry detergent or lowering of the cloud point of a liquid detergent. The minimum amount is determined not only by the particular detergent present but also by the presence of other hydrotropes. In general, an economic limitation exists whereas no worthwhile improvement is obtained with further addition of this hydrotrope.
  • the usage of the defined alkylethoxy sulfate hydrotrope is between about 2 and 10% and more usually about -10%. In the case of liquid, light or heavy duty detergent compositions, the usage is between about 5 and 15% and more usually about -15%.
  • alkylethoxy sulfates are available as aqueous solutions. It is to be understood the aforesaid usages are based on 100% active material.
  • Liquid, light-duty detergent compositions include, in addition to the alkylbenzene sulfonate detergent and hydrotrope, either a foam stabilizer or another detergent or both. Any of the foam stabilizers now used may be used with the defined hydrotrope.
  • amine oxides members of the fatty alcohol series, such as lauryl alcohol; fatty diethanolamides, such as coco-fatty diethanolamide; fatty alkylamides; free fatty acids and their esters with lower monohydric alcohols or glycols; saponins; higher aliphatic 1,2-diols, such as hexadecane-1,2-diol; imides of dicarboxy acids, such as 4-Octadecene-1,2-dicarboxylic acid imide; and esters of aryl phosphoric acid, such as the sodium salt of the methylester of p-tert-octylbenzenephosphoric acid.
  • fatty alcohol series such as lauryl alcohol
  • fatty diethanolamides such as coco-fatty diethanolamide
  • fatty alkylamides free fatty acids and their esters with lower monohydric alcohols or glycols
  • saponins higher aliphatic 1,2-diols, such as hexade
  • the other detergent may be an ethoxy nonionic detergent or an alkylethoxy sulfate detergent having at least about 12 alkyl carbon atoms.
  • the thoxy nonionic detergent preferably has 10-18 alkyl carbon atoms and about 50-65% ethylene oxide unit content.
  • Operable materials include the condensation product of ethylene oxide with a fatty acid-containing material such as tall oil, alcohols, esters, aldehydes, amids, amines, a phenolic compound having lateral alkyl side chains, and the like.
  • Liquid heavy-duty detergent compositions include, in addition to the above-named ingredients of the light-duty formulations, a potassium polyphosphate compound.
  • the complex or molecularly dehydrated polyphosphate salts are generally used in the form of the normal or completely neutralized salts, e.g., tetrapotassium pyrophosphate and pentapotassium tripolyphosphate.
  • Partially neutralized salts, such as potassium acid tripolyphosphate may also be used. Mixtures of these materials may be used, but it is preferred that such mixtures include an effective amount of tetrapotassiurn pyrophosphate.
  • a particular embodiment of a slurry detergent composition, of the invention consists essentially of (a) alkylbenzene sulfonate having about 12 alkyl carbon atoms derived from propylene tetramer, about 40%; (b) sodium sulfate, about 5%; (c) hexylethoxy sulfate having about 2 ethylene oxide units, about 5%; and (d) liquid water, about 50%.
  • the sodium sulfate in gredient enhances detergency power but is not an essential ingredient of the formulation.
  • a foam stabilizer When a foam stabilizer is part of the light or heavy duty composition, it is present in an amount of about 210%. When the other defined detergent is part of the light or heavy duty composition, it is present in an amount of about 10-25%; should more than one of the other defined detergents be present, the total content is about 10-25%.
  • ingredients may be added to the detergent composition as desired, including compatible perfumes, coloring materials, corrosion or antitarnishing inhibitors, e.g., silicates, germicides, bleaching agents, optical bleaches or fluorescent brighteners, and the like. It is desirable to add a minor amount, such as A1-5% by weight, of a soil anti-redeposition agent, e.g., cellulose ethers. Suitable examples are methyl-, ethyl-, and hydroxyethylcellulose, alkali metal carboxymethylcellulose. In some cases, a lower alcohol may be present.
  • a soil anti-redeposition agent e.g., cellulose ethers. Suitable examples are methyl-, ethyl-, and hydroxyethylcellulose, alkali metal carboxymethylcellulose. In some cases, a lower alcohol may be present.
  • An especially suitable liquid, light-duty detergent composition includes (a) linear alkylbenzene sulfonate having about 12 'alkyl carbon atoms, about 25%; (b) lauric diethanolamide foam stabilizers, about 5%; (c) hexylethoxy sulfate having about 2 ethylene oxide units, about 10%; and (d) liquid water essentially the remainder.
  • the anionic detergents and sulfates which are or may be present in the detergent compositions of the invention are used in the form of their water-soluble salts, such as the alkali metal, alkaline earth metal, ammonium, amine, and alkylolamine salts. While the sodium, potassium, ammonium, and alkylolamine (e.g., mono-, di-, and triethanolamine) salts are preferred ordinarily, other salts such as the lithium, calcium, and magnesium salts may be used if desired. For general use, it is preferred to use the sodium and potassium salts.
  • a slurry detergent in an as produced condition had an unmanageable high viscosity.
  • the as produced slurry analyzed: propylene tetramer-benezene 5 HI sulfonate (sodium) 46%- sodium sulfate 5% unreacted Liquid light duty detergents were formulated which all; lbenzene, about 17 and water 487 y differed only in the detergent present.
  • Each formulation Ia included 25% of detergent; 5% of lauric diethanolamide
  • a typical commercial formulation was prepared by foam stablhzer; f the remamder Wateradding 5 parts of xylene sulfonate hydrotrope to 100 For comparatfve 17111130565 east ⁇ of the QY formula parts by Weight of the as produced Slurry.
  • the Xylene trons was made nto a corresponding composition by addsulfonate was in the form of an aqueous solution containmg of acme hydrotrope- These lncludefi the ing about 40% of the active materiaL ventional hydrotropes: ethanol, urea and sod1um xylene sulfonate.
  • sod1um hexyl sulfate was added- 1b this was made by sulfating ALFOL 6 alcohol.
  • a comparative formulation was prepared by adding 12 another, Sodium h xyl xy Sulfate was parts of liquid Water to 100 parts of the as produced ildded- T Cloud was detefmlned for each Slurry composition.
  • Formulation IIIa contained propylene 1c tetramerbenzene sulfonate (sodium).
  • Formulation IIIb c Another formulation was Prepared by addmg 10 Parts sillillilioi liii coiliiiii iiiifi nfiiiifiilialiii fii :1 1d 2 i t s g f li iiit i v itfiir ilf5$ffigg by sulfating Arrow 1218 alcohol which is a mixture of P q Y n-alkanols having 12, 14, 16, and 18 carbon atoms.
  • composition of claim 1 wherein said sulfonate is a linear alkylbenzene sulfonate.
  • a slurry detergent composition consisting of:
  • alkylbenzene sulfonate having about 12 alkyl carbon atoms derived from propylene tetramer, about 40% by weight;
  • a liquid, light-duty detergent composition consisting of:
  • alkylethoxy sulfate having 4-8 alkyl carbon atoms and about 15-55% by weight of ethylene oxide units, 5
  • alkylethoxy sulfate detergent having at least about 12 alkyl carbon atoms, wherein said detergent is present in a total of about 1025% by weight
  • liquid detergent composition of claim 4 wherein said sulfonate is linear alkylbenzene sulfonate.
  • liquid detergent composition of claim 4 wherein said nonionic detergent is alkanol ethoxy ether having 10-18 alkanol carbon atoms and about 50-65% by weight ethylene oxide units.
  • a liquid, light-duty detergent composition consisting (a) linear alkylbenzene sulfonate having about 12 alkyl carbon atoms, about 25% by weight;
  • a liquid, heavy-duty detergent composition consisting of (a) alkylbenzene sulfonate having about 8-16 alkyl carbon atoms, about 13-25% by weight;
  • alkylethoxy sulfate having 4-8 alkyl carbon atoms and about 15-55 by weight of ethylene oxide units, in an amount of about 5-15 by weight;
  • alkylethoxy sulfate detergent having at least about 12 alkyl carbon atoms, wherein said detergent is present in a total of about 10-25% by weight
  • liquid detergent composition of claim 7 wherein said sulfonate is linear alkylbenzene sulfonate.

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  • Chemical & Material Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Wood Science & Technology (AREA)
  • Organic Chemistry (AREA)
  • Detergent Compositions (AREA)
US652017A 1964-07-22 1967-07-10 Detergent-hydrotrope composition Expired - Lifetime US3501409A (en)

Applications Claiming Priority (2)

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US38453964A 1964-07-22 1964-07-22
US65201767A 1967-07-10 1967-07-10

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US3501409A true US3501409A (en) 1970-03-17

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US (1) US3501409A (fr)
BE (1) BE679573A (fr)
CH (1) CH456820A (fr)
DE (1) DE1467572A1 (fr)
GB (1) GB1105905A (fr)
NL (1) NL6509345A (fr)

Cited By (16)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3925227A (en) * 1972-05-31 1975-12-09 American Home Prod Novel laundering compositions
US4018720A (en) * 1975-07-14 1977-04-19 The Procter & Gamble Company Laundry detergent compositions in emulsion/suspension
US4024078A (en) * 1975-03-31 1977-05-17 The Procter & Gamble Company Liquid detergent composition
US4040989A (en) * 1973-05-25 1977-08-09 Colgate-Palmolive Company Liquid detergent
US4532067A (en) * 1984-01-11 1985-07-30 Lever Brothers Company Liquid detergent compositions containing hydroxypropyl methylcellulose
US4731201A (en) * 1986-08-12 1988-03-15 Colgate-Palmolive Company Shampoo method and composition
US4732703A (en) * 1984-02-16 1988-03-22 Lever Brothers Company Liquid detergent compositions containing stabilizers to prevent phase separation
US4743385A (en) * 1984-11-21 1988-05-10 Sun Refining And Marketing Company Oil recovery agent
US4769161A (en) * 1984-12-14 1988-09-06 Sun Refining And Marketing Company Silicate-containing oil recovery compositions
US5607910A (en) * 1993-06-30 1997-03-04 Sherry; Alan E. Detergent gels containing ethoxylated alkyl sulfates and secondary sulfonates
US20050049165A1 (en) * 2001-08-07 2005-03-03 Beatrix Kottwitz Detergent and cleaning agent with hybrid alpha-amylases
US9018177B2 (en) 2012-10-12 2015-04-28 L'oreal S.A. Cosmetic compositions for increasing bioavailability of the active compounds baicalin and/or vitamin C
US9023826B2 (en) 2012-10-12 2015-05-05 L'oreal S.A. Compositions containing adenosine and the hydrotropes caffeine and nicotinamide for cosmetic use
US9072919B2 (en) 2012-10-12 2015-07-07 L'oreal S.A. Synergistic antioxidant cosmetic compositions containing at least one of baicalin and taxifolin, at least one of caffeine and nicotinamide, at least one of vitamin C and resveratrol and ferulic acid
US9107853B2 (en) 2012-10-12 2015-08-18 L'oreal S.A. Compositions containing phenolic compounds and hydrotropes for cosmetic use
US9669242B2 (en) 2013-07-01 2017-06-06 L'oreal Compositions containing at least two phenolic compounds, a lipid-soluble antioxidant and at least one hydrotrope for cosmetic use

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE2743607A1 (de) * 1977-09-28 1979-04-05 Huels Chemische Werke Ag Waessrige reinigungsmittelloesungen

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3140261A (en) * 1960-11-15 1964-07-07 Shell Oil Co Detergent composition
US3231504A (en) * 1961-02-03 1966-01-25 Colgate Palmolive Co Liquid detergent compositions

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3140261A (en) * 1960-11-15 1964-07-07 Shell Oil Co Detergent composition
US3231504A (en) * 1961-02-03 1966-01-25 Colgate Palmolive Co Liquid detergent compositions

Cited By (17)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3925227A (en) * 1972-05-31 1975-12-09 American Home Prod Novel laundering compositions
US4040989A (en) * 1973-05-25 1977-08-09 Colgate-Palmolive Company Liquid detergent
US4024078A (en) * 1975-03-31 1977-05-17 The Procter & Gamble Company Liquid detergent composition
US4018720A (en) * 1975-07-14 1977-04-19 The Procter & Gamble Company Laundry detergent compositions in emulsion/suspension
US4532067A (en) * 1984-01-11 1985-07-30 Lever Brothers Company Liquid detergent compositions containing hydroxypropyl methylcellulose
US4732703A (en) * 1984-02-16 1988-03-22 Lever Brothers Company Liquid detergent compositions containing stabilizers to prevent phase separation
US4743385A (en) * 1984-11-21 1988-05-10 Sun Refining And Marketing Company Oil recovery agent
US4769161A (en) * 1984-12-14 1988-09-06 Sun Refining And Marketing Company Silicate-containing oil recovery compositions
US4731201A (en) * 1986-08-12 1988-03-15 Colgate-Palmolive Company Shampoo method and composition
AU601996B2 (en) * 1986-08-12 1990-09-27 Colgate-Palmolive Company, The Shampoo method and composition
US5607910A (en) * 1993-06-30 1997-03-04 Sherry; Alan E. Detergent gels containing ethoxylated alkyl sulfates and secondary sulfonates
US20050049165A1 (en) * 2001-08-07 2005-03-03 Beatrix Kottwitz Detergent and cleaning agent with hybrid alpha-amylases
US9018177B2 (en) 2012-10-12 2015-04-28 L'oreal S.A. Cosmetic compositions for increasing bioavailability of the active compounds baicalin and/or vitamin C
US9023826B2 (en) 2012-10-12 2015-05-05 L'oreal S.A. Compositions containing adenosine and the hydrotropes caffeine and nicotinamide for cosmetic use
US9072919B2 (en) 2012-10-12 2015-07-07 L'oreal S.A. Synergistic antioxidant cosmetic compositions containing at least one of baicalin and taxifolin, at least one of caffeine and nicotinamide, at least one of vitamin C and resveratrol and ferulic acid
US9107853B2 (en) 2012-10-12 2015-08-18 L'oreal S.A. Compositions containing phenolic compounds and hydrotropes for cosmetic use
US9669242B2 (en) 2013-07-01 2017-06-06 L'oreal Compositions containing at least two phenolic compounds, a lipid-soluble antioxidant and at least one hydrotrope for cosmetic use

Also Published As

Publication number Publication date
DE1467572A1 (de) 1969-01-23
NL6509345A (fr) 1966-01-24
CH456820A (fr) 1968-05-31
BE679573A (fr) 1966-09-16
GB1105905A (en) 1968-03-13

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AS Assignment

Owner name: VISTA CHEMICAL COMPANY, 15990 NORTH BARKERS LANDIN

Free format text: ASSIGNMENT OF ASSIGNORS INTEREST. SUBJECT TO TERMS OF AGREEMENT DATED JUNE 26,1984;ASSIGNOR:CONOCO INC.;REEL/FRAME:004349/0285

Effective date: 19840720