US3734859A - Dicarboxylic acid soaps - Google Patents

Dicarboxylic acid soaps Download PDF

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Publication number
US3734859A
US3734859A US00188458A US3734859DA US3734859A US 3734859 A US3734859 A US 3734859A US 00188458 A US00188458 A US 00188458A US 3734859D A US3734859D A US 3734859DA US 3734859 A US3734859 A US 3734859A
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soap
soaps
dicarboxylic acid
fatty acids
acid
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B Ward
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Westvaco Corp
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Westvaco Corp
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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
    • C11D17/00—Detergent materials or soaps characterised by their shape or physical properties
    • C11D17/08—Liquid soap, e.g. for dispensers; capsuled
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
    • A61K8/36—Carboxylic acids; Salts or anhydrides thereof
    • A61K8/362—Polycarboxylic acids
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q19/00—Preparations for care of the skin
    • A61Q19/10—Washing or bathing preparations
    • 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
    • C11D9/00—Compositions of detergents based essentially on soap
    • C11D9/005—Synthetic soaps
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q5/00—Preparations for care of the hair
    • A61Q5/02—Preparations for cleaning the hair

Definitions

  • soap of the above composition may be blended at from 5% to 90% by soap weight with coconut fatty acids, tallow fatty acids, tall oil fatty acids, oleic acid, soya fatty acids, safflower oil and other fatty acids, and retain the advantageous properties of using C dicarboxylic acid soaps alone.
  • the soaps and soap blends are water soluble not only at low solids concentration but also at high solids concentration, for example, above 40% solids and in some cases above 90% solids.
  • the soap compositions find utility among other places as liquid hand soaps, cleaning aids and shampoos.
  • This invention relates to novel soap compositions. More particularly, this invention relates to soap compositions containing a C dicarboxylic acid soap having improved solubility characteristics and blends of the C dicarboxylic acid soaps with other fatty acid soaps.
  • x and y are integers from 3 to 9, x and y together equal 12
  • Z is a member of the group consisting of hydrogen and COOM with one Z of each moiety
  • M and M are selected from the group consisting of hydrogen, sodium, potassium, lithium, ammonium, amines and mixtures thereof in an amount suflicient to impart detergency to said composition.
  • the dicarboxylic acid soaps may be mixed or blended with from about 5% to about by weight of soap solids of fatty acid soaps selected from the group consisting of coconut soaps, tallow soaps, tall oil soaps, soya soaps, oleic-acid soap, safiiower soaps and mixtures thereof. Both the C dicarboxylic acid soaps alone and the blends have a greater water solubility than fatty acids soaps.
  • the essence of this invention is the discovery that when a mixture of predominately 5 carboxy-4-hexyl-2-cyclohexene-l-octanoic acid and 6 carboxy-4-hexyl-2 cyclohexene-l-octanoic acid is converted into soap the isomer mixture formed provides not only the advantages of conventional soaps, such as coconut soaps, tallo-w soap and oleic soaps, but also provides additional advantages such as, in particular, increased water solubility.
  • x and y are integers from 3 to 9, x and y together equal 12
  • Z is a member of the group consisting of hydrogen and COOM with one Z of each moiety
  • M and M are selected from various neutralizing agents.
  • C dicarboxylic acid where cyclohexene ring varies in position along the carbon chain.
  • compositions of the general formulation shown above are termed C dicarboxylic acid soaps and in the acid form are termed C dicarboxylic acid.
  • the C dicarboxylic acids used in this invention are produced from linoleic acid of various animal, vegetable and tall oil sources.
  • the C dicarboxylic acids may be made by reacting linoleic acid with acrylic acid and catalytic amounts of iodine.
  • One such process for making the dicarboxylic acids for use in the soaps of this invention is set forth in my co-pending application, Ser. No. 159,070 filed July 2, 1971, now abandoned.
  • the C dicarboxylic acid soaps are made by neutralizing the C dicarboxylic acid.
  • the neutralizing agent used is based on the solubility characteristics desired in the soap and economic considerations.
  • the neutralizing agents contemplated include those of the following cations, sodium, potassium, lithium and ammonium. These cations may be obtained from such inorganic alkalis as caustic soda, caustic potash, and soda ash. Another cation which may be used is the ammonium cation.
  • Organic amines may also be used, specifically amines such as triethylamine, monoethylamine, diethylamine, and alkanolamines, such as ethanolamine, triethanolamine and diethanolamine.
  • the soaps made from the above listed neutralizing agents are all liquid at temperatures as low as 30 F.
  • the C dicarboxylic acid soaps are not only more soluble themselves, but lend increased water solubility to soaps made by blending the C dicarboxylic acid soaps with other fatty acid soaps, such as oleic acid soap and coconut soaps.
  • the potassium soap of oleic acid is a viscous fluid at about 18% solids and gels at 19%20% solids.
  • the potassium soap of oleic acid blended with 40% C dicarboxylic acid potassium soap is very fluid at 30 to 40% solids. This general characteristic of increased solubility is advantageous to all soap users for economy in shipping and handling.
  • a property of the soaps which points up this solubility advantage of C dicarboxylic acid soap and which is also important for C dicarboxylic acid utility is the viscosity of the soap. If viscosity of the solution at 25 C. is plotted against percentage real soap, curves are obtained which dramatically demonstrate the superior characteristics of the C dicarboxylic acid soap.
  • the solubility of the various soaps may be illustrated by the viscosity of the soaps which is shown in the accompanying figure. Whereas, the viscosity of the potassium soap solution of oleic acid exceeds twenty centipoises at 16% real soap, a solution of the potassium soap of C dicarboxylic acid does not exceed twenty centipoises until it is 35 real soap.
  • the coconut fatty acid potassium soap is somewhat poorer than the C dicarboxylic acid soap since its viscosity goes above twenty centipoises at 30% real soap.
  • the C dicarboxylic acid soap also makes low viscosity blends with oleic acid soap as it does with the coconut soap.
  • liquid soaps When making liquid soaps, other additives commonly used may be included in the final compositions. Among these include minor amounts of coloring agents, perfumes and antimicrobial agents.
  • One such agent used is the disinfectant pine oil, which is readily compatible with C dicarboxylic acid soap solutions.
  • the liquid soaps may have as little as 2.5% water, but for easier dispensing and handling, the liquid soap contains less than 60% water or, in other words, the real soap content of the C dicarboxylic acid soaps may be greater than 40% for economy in shipping.
  • C dicar boxylic acids Another property which is applicable to C dicar boxylic acids in any application is the ability to form a soluble mono soap.
  • Most fatty acid soaps are made from molecules containing one acid group per molecule and before that molecule can become water-soluble it must be converted to the soap.
  • the C dicarboxylic acid becomes water-soluble when only one-half of the carboxyl groups exist as carboxylate anions. Since each molecule of C dicarboxylic acid has two carboxyl groups of varying acidity it is possible to convert the most acidic of these to the soap and the molecule becomes watersoluble leaving a free acid group on each molecule.
  • These mono soap solutions have a pH of about 6.6 and are soluble over a broad solids range, i.e., 2% to 99+% on water.
  • the mono soaps of potassium, sodium, ammonia, and organic amines all show the same type properties.
  • the fact that the mono soap is water-soluble allows one to have considerable leverage in the amount of free acid and thus the pH of a soap solution.
  • a soap solution of C dicarboxylic acid can be prepared at any pH above 6.5, so in the case of amine soaps one can prepare the soap in such a way as to have free acid groups rather than excess amine, so there is no amine odor.
  • the C dicarboxylic acid soaps have great utility strictly as soaps.
  • the viscosity must be kept at a very low level for economics of shipping and ease of dispensing the soap. This is the main reason that coconut fatty acids are currently used in this area.
  • the hospital scrub soaps on the other hand do not have to be as economical, so C type fatty acid mixtures are often used at low concentrations.
  • the obvious advantages of C dicarboxylic acid soaps in this area would be for preparing more concentrated soaps and for cutting costs by using sodium cations.
  • Several liquid cleaners currently on the market use fatty acids as the soap component and more will switch from synthetic detergents to fatty acids as more emphasis is placed on ecology.
  • liquid soaps whether they be hand soaps, hospital scrub soaps, dishwashing liquids, floor cleaners, or others are to be made from oleic-type fatty acids
  • the maximum amount of soap that can be present in water is about 15%. If short chain coconut fatty acids are used this percentage can be raised to about 35%, but at the percentages higher than 20% the viscosity increases rapidly.
  • C fatty acids are used only in the hospital scrub soaps and in liquid hand soaps; however, with the variable concentrations and cations available when C dicarboxylic acid is used, a decrease in use of synthetic detergents could result.
  • Liquid hand soaps normally have a perfume in them, pine oil being the most common. Pine oil is very compatible with the C dicarboxylic acid soaps and therefore, perfuming is no problem.
  • a product similar to the liquid soaps in composition is shampoo.
  • shampoos are simply perfumed soap solutions which need to lather easily and which have a fairly high soap content. Consequently, most shampoos consist from 50% to 100% of the solids as coconut fatty acid soaps. With such a formulation a viscous potassium soap of about 35% real soap (solids) can be prepared. If the triethanolamine soap is used, a 40% real soap may be formulated.
  • C dicarboxylic acid soap would allow for greater flexibility in the amount of soap present in the shampoo and also allow for the utility of a lower priced cation, sodium. The problem of coconut fatty acids tendency to cause skin irritation might also be eliminated.
  • EXAMPLE 1 As one of the advantages of this invention is to produce a high concentration liquid, i.e., liquid above 20% solids concentration, the water solubility characteritics of a number of conventionally used fatty acid soaps were compared to the C dicarboxylic acid soaps of this invention. Likewise, just as the type of fatty acid used influences soap properties, so does the choice of neutralizing agent. Therefore, various available inorganic alkalis were also compared.
  • the procedure for making the fatty acid soaps was to dissolve the inorganic alkali in the prescribed amount of water, heating to 150 F. The fatty acid was slowly added to the alkali solution and agitated for a few minutes. The characteristics of each formulation are shown in the table below.
  • soaps of C dicarboxylic acid are water soluble at higher solids content than are soaps of conventional fatty acids, such as coconut fatty acids, vegetable derived oleic acid and tall oil fatty acids, among others. Also the potassium soaps are more soluble than sodium.
  • EXAMPLE 2 Another aspect of this invention is that the C dicarboxylic acid soaps when blended with other fatty acid soaps such as tall oil fatty acid soaps, gives a blended mixture having, a greater water solubility than the conventional fatty acid used alone.
  • the C dicarboxylic acid used to prepare all of these blends was actually about 93% C dicarboxylic acid, 3% C 'dimer acids and about 4% fatty acids.
  • the fatty acid soap used was a distilled, disproportionated tall oil fatty acid sold by Westvaco Corporation under the trademark Westvaco 1480.
  • the results of the potassium soap blends are shown in Table IIA wherein the C dicarboxylic acid soap is referred to as diacid and the distilled, disproportionated tall oil fatty acid soap is referred to as fatty acid.
  • the sodium C dicarboxylic acid soap increases the solubility of the sodium tall oil fatty acid soap. Since the initial solubility is so much less than with potassium soap, about 20% C dicarboxylic acid soap must be present before the 10% soap is a clear solution.
  • EXAMPLE 3 TABLE 111 Percent Characteristics Soap solids at 25 C 100% coconut fatty acid 38 Gel. 90% diacid/l0% coconut acid 40 Solution. 60% diacid/50% coconut acid 40 Do. 100% tallow 5 Gel. 50% diacid/50% tallow. 5 Turbid solution.
  • EXAMPLE 4 This example illustrates a comparison of viscosity changes with potassium solids.
  • Liquid soaps of fatty acids must be fairly fluid for ease in dispensing and using them. Therefore, a measure of the change in viscosity of a soap solution as percentage soap present increases is an easy method for determining the concentration of soap that can be used.
  • the curves in the accompanying figure show this relationship.
  • a Brookfield viscometer was used to determine these curves at 25 C. As is shown by the graph, the C discarboxylic acid soap and blends containing C dicarboxylic acid soap are significantly better than oleic-type soap and coconut fatty acid soap as far as increase in viscosity with soap solids is concerned.
  • the C dicarboxylic acid-amine soaps were also prepared using diethanolamine and monoethanol amine. All of the amine soaps showed unusual solubility just as had the sodium and potassium soaps.
  • the mono-soaps of C dicarboxylic acid are soluble in water at high solids levels. Of course, these soaps all have a pH of about 6.7 and have one free carboxylic acid group in solution.
  • the mono-soap is prepared by simply adding one equivalent of base to the C dicarboxylic acid and allowing the solution to reach equilibrium.
  • An example of utility for a mono-soap is in the textile industry where fiber processing aids are of great importance. A piece of cotton was soaked in a solution of a mono potassium soap of C dicarboxylic acid and then dried, the cloth absorbed 1.8% of its weight in the soap which could not be washed out with water. The absorbed soap gave the cloth better hand when wet or dry. The mono-soap was easily removed bypassing the cloth through caustic to convert the mono-soap to the di-soap which was readily washed out.
  • EXAMPLE 7 To demonstrate that the C dicarboxylic acid soap could be used in liquid soaps, several soaps were prepared in accordance with typical formulations. The formulation used was 12% coconut fatty acids, 3% soya or tall oil fatty acid, 4.4% KOH, 1% KCL, 80% Water and a perfume as desired. In all of the soaps pine oil was added as the perfume at 3% addition.
  • EXAMPLE 9 An area closely related to the liquid soaps is shampoos.
  • the formulations are similar but, since profuse sudsing is desired in shampoos and since low viscosity is not critical, the real soap content is more than twice as high.
  • coconut fatty acids or a blend of 50% coconut-50% oleic must be used.
  • a 40% soap shampoo can be prepared using triethanolamine rather than potassium hydroxide to form the soap.
  • very comparable shampoos were prepared using C dicarboxylic acid or a C dicarboxylic acid-oleic blend.
  • C dicarboxylic acid has a major economic advantage in this application since sodium hydroxide could be used instead of potassium hydroxide.
  • more concentrated soaps can be made using C dicarboxylic acid since it does not gel even at 99% solids.
  • a soap composition consisting of a compound of the formula wherein x and y are integers from 3 to 9, x and y together equal 12, Z is a member of the group consisting of H and COOM with one Z of each moiety, and M and M are selected from the group consisting of hydrogen, sodium, potassium, lithium, ammonium and mixture thereof.
  • a liquid soap composition consisting essentially of a compound of the formula CH-CH t Z wherein x and y are integers from 3 to 9, x and y together equal 12, Z is a member of the group consisting of H and COOM with one Z of each moiety, and M and M are selected from the group consisting of hydrogen, sodium, potassium, lithium, ammonium and mixtures thereof present in an amount of 5% to 95% by weight soap solids; a soap selected from the group consisting of coconut fatty acids, tallow fatty acids, tall oil fatty acids, oleic acid, soya fatty acids, safflower fatty acids, and mixtures thereof being present in the amount of to 5% by weight soap solids.
  • the soap composition of claim 4 containing from a out 40% to 60% by weight real soap content.
  • liquid soap composition of claim 4 further containing less than 60% water.
  • the soap composition of claim 10 being liquid and containing less than 15% water.
  • a soap composition consisting of a compound of the formula wherein x and y are integers from 3 to 9, x and y together equal 12, Z is a member of the group consisting of H and COOM with one Z of each moiety, and M and M are selected from the group consisting of hydrogen, inorganic alkalis, and organic amines.

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Cited By (24)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3926893A (en) * 1974-08-26 1975-12-16 Westvaco Corp Polish containing a C{HD 21 {B -cycloaliphatic dicarboxylic acid
US3931029A (en) * 1974-10-15 1976-01-06 Basf Wyandotte Corporation Corrosion inhibited antifreeze compositions and process for inhibiting the corrosion of solder alloys
US3956161A (en) * 1974-06-03 1976-05-11 Westvaco Corporation Cleaning compositions containing C21 dicarboxylic acid
US3966628A (en) * 1974-08-21 1976-06-29 Westvaco Corporation Solid cleaning compositions containing C21 dicarboxylic acid
US4063886A (en) * 1976-06-01 1977-12-20 Westvaco Corporation Mercerizing compositions
US4080164A (en) * 1976-06-01 1978-03-21 Westvaco Corporation Textile scouring
US4081462A (en) * 1975-10-14 1978-03-28 Westvaco Corporation C22 -Cycloaliphatic tricarboxylic fatty acid soaps
US4081395A (en) * 1975-10-14 1978-03-28 Pennwalt Corporation Alkaline detergent compositions
US4196134A (en) * 1977-01-31 1980-04-01 Westvaco Corporation Vegetable oil adducts
US4548810A (en) * 1979-05-03 1985-10-22 Albert Zofchak Method of lubricating the skin
US4744916A (en) * 1985-07-18 1988-05-17 Colgate-Palmolive Company Non-gelling non-aqueous liquid detergent composition containing higher fatty dicarboxylic acid and method of use
US4770803A (en) * 1986-07-03 1988-09-13 The Lubrizol Corporation Aqueous compositions containing carboxylic salts
US4983317A (en) * 1984-06-08 1991-01-08 The Drackett Company All purpose cleaner concentrate composition
US5073293A (en) * 1988-09-20 1991-12-17 Kao Corporation Mild detergent compositions containing alkylglycoside and dicarboxylic acid surfactants
US5324847A (en) * 1990-01-24 1994-06-28 Henkel Kommanditgesellschaft Auf Aktien Olefinically unsaturated adducts of ethylene with polyunsaturated fatty acids of fatty acid esters, a process for their production and their use
US5401865A (en) * 1990-01-24 1995-03-28 Henkel Kommanditgesellschaft Auf Aktien Saturated branched fatty acids containing 21 to 28 carbon atoms or esters thereof with c1-36 alkanols, a process for their production and their use
US5420317A (en) * 1990-01-24 1995-05-30 Henkel Kommanditgesellschaft Auf Aktien Olefinically unsaturated adducts of propylene with polyunsaturated fatty acid or fatty acids esters, a process for their production and their use
US5481025A (en) * 1990-01-24 1996-01-02 Henkel Kommanditgesellschaft Auf Aktien Tfp/Patentabteilung Saturated branched fatty acids containing 20 to 28 carbon atoms or esters thereof with C1-36 alkanols, a process for their production and their use
US5736503A (en) * 1992-11-30 1998-04-07 The Procter & Gamble Company High sudsing detergent compositions with specially selected soaps
USRE36479E (en) * 1986-07-03 2000-01-04 The Lubrizol Corporation Aqueous compositions containing nitrogen-containing salts
DE10219295A1 (de) * 2002-04-25 2003-11-13 Coty Bv Flüssige kosmetische Reinigungszusammensetzung
WO2005037971A1 (de) * 2003-10-09 2005-04-28 Beiersdorf Ag Temperaturstabile kosmetische reinigungszubereitung mit dicarbonsäuren
US20050198747A1 (en) * 2004-02-27 2005-09-15 Winfried Emmerling Use of cationic starch derivatives for dye retention
US20100047202A1 (en) * 2006-12-21 2010-02-25 Henkel Ag & Co.Kgaa Hair-Conditioning Agents Containing Selected Cationic Polymers and Water-Soluble Silicones

Families Citing this family (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3984356A (en) * 1975-08-20 1976-10-05 Morton-Norwich Products, Inc. Liquid laundering detergent and softener
CA1071969A (en) * 1976-03-25 1980-02-19 Pennwalt Corporation Alkaline detergent compositions
GB8525503D0 (en) * 1985-10-16 1985-11-20 Unilever Plc Detergent component
DE102006061555A1 (de) 2006-12-27 2008-07-03 Henkel Kgaa Synergistische Kombination von Seidenproteinen und ausgewählten Metallen
DE102007001008A1 (de) 2007-01-02 2008-07-03 Henkel Kgaa Kosmetische Wirkstoffzusammensetzung mit Ayurveda-Extrakten
DE102007001028A1 (de) 2007-01-02 2008-07-03 Henkel Kgaa Kosmetische Zusammensetzung enthaltend Arganöl und Sheabutter
DE102007001019A1 (de) 2007-01-02 2008-07-03 Henkel Kgaa Natürliche mineralische Pulver in kosmetischen Mitteln
DE102007001027A1 (de) 2007-01-02 2008-07-03 Henkel Kgaa Kosmetische Zusammensetzungen enthaltend ausgewählte Fettsäuren und Squalen
DE102009009004A1 (de) 2008-02-18 2009-09-17 Seaquist Perfect Dispensing Gmbh Abgabevorrichtung mit einem kosmetischen Fluid
DE102009031432A1 (de) 2009-07-01 2011-01-05 Henkel Ag & Co. Kgaa Kompaktes Haarspray

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3538009A (en) * 1967-02-01 1970-11-03 Cincinnati Milling Machine Co Method for reducing skin irritation in detergent compositions
DE1617227C3 (de) * 1967-07-12 1975-01-23 Unilever N.V., Rotterdam (Niederlande) Reinigungsmittel, insbesondere Wasch-Mlttel mit thermoreguliertem Schaum

Cited By (26)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3956161A (en) * 1974-06-03 1976-05-11 Westvaco Corporation Cleaning compositions containing C21 dicarboxylic acid
US3966628A (en) * 1974-08-21 1976-06-29 Westvaco Corporation Solid cleaning compositions containing C21 dicarboxylic acid
US3926893A (en) * 1974-08-26 1975-12-16 Westvaco Corp Polish containing a C{HD 21 {B -cycloaliphatic dicarboxylic acid
US3931029A (en) * 1974-10-15 1976-01-06 Basf Wyandotte Corporation Corrosion inhibited antifreeze compositions and process for inhibiting the corrosion of solder alloys
US4081462A (en) * 1975-10-14 1978-03-28 Westvaco Corporation C22 -Cycloaliphatic tricarboxylic fatty acid soaps
US4081395A (en) * 1975-10-14 1978-03-28 Pennwalt Corporation Alkaline detergent compositions
US4063886A (en) * 1976-06-01 1977-12-20 Westvaco Corporation Mercerizing compositions
US4080164A (en) * 1976-06-01 1978-03-21 Westvaco Corporation Textile scouring
US4196134A (en) * 1977-01-31 1980-04-01 Westvaco Corporation Vegetable oil adducts
US4548810A (en) * 1979-05-03 1985-10-22 Albert Zofchak Method of lubricating the skin
US4983317A (en) * 1984-06-08 1991-01-08 The Drackett Company All purpose cleaner concentrate composition
AU591146B2 (en) * 1985-07-18 1989-11-30 Colgate-Palmolive Company, The Non-gelling liquid detergent composition containing higher fatty dicarboxylic acid and method of use
US4744916A (en) * 1985-07-18 1988-05-17 Colgate-Palmolive Company Non-gelling non-aqueous liquid detergent composition containing higher fatty dicarboxylic acid and method of use
US4770803A (en) * 1986-07-03 1988-09-13 The Lubrizol Corporation Aqueous compositions containing carboxylic salts
USRE36479E (en) * 1986-07-03 2000-01-04 The Lubrizol Corporation Aqueous compositions containing nitrogen-containing salts
US5073293A (en) * 1988-09-20 1991-12-17 Kao Corporation Mild detergent compositions containing alkylglycoside and dicarboxylic acid surfactants
US5481025A (en) * 1990-01-24 1996-01-02 Henkel Kommanditgesellschaft Auf Aktien Tfp/Patentabteilung Saturated branched fatty acids containing 20 to 28 carbon atoms or esters thereof with C1-36 alkanols, a process for their production and their use
US5420317A (en) * 1990-01-24 1995-05-30 Henkel Kommanditgesellschaft Auf Aktien Olefinically unsaturated adducts of propylene with polyunsaturated fatty acid or fatty acids esters, a process for their production and their use
US5401865A (en) * 1990-01-24 1995-03-28 Henkel Kommanditgesellschaft Auf Aktien Saturated branched fatty acids containing 21 to 28 carbon atoms or esters thereof with c1-36 alkanols, a process for their production and their use
US5324847A (en) * 1990-01-24 1994-06-28 Henkel Kommanditgesellschaft Auf Aktien Olefinically unsaturated adducts of ethylene with polyunsaturated fatty acids of fatty acid esters, a process for their production and their use
US5736503A (en) * 1992-11-30 1998-04-07 The Procter & Gamble Company High sudsing detergent compositions with specially selected soaps
DE10219295A1 (de) * 2002-04-25 2003-11-13 Coty Bv Flüssige kosmetische Reinigungszusammensetzung
DE10219295B4 (de) * 2002-04-25 2008-09-18 Coty B.V. Flüssige kosmetische Reinigungszusammensetzung
WO2005037971A1 (de) * 2003-10-09 2005-04-28 Beiersdorf Ag Temperaturstabile kosmetische reinigungszubereitung mit dicarbonsäuren
US20050198747A1 (en) * 2004-02-27 2005-09-15 Winfried Emmerling Use of cationic starch derivatives for dye retention
US20100047202A1 (en) * 2006-12-21 2010-02-25 Henkel Ag & Co.Kgaa Hair-Conditioning Agents Containing Selected Cationic Polymers and Water-Soluble Silicones

Also Published As

Publication number Publication date
CA975796A (en) 1975-10-07
FR2156305A1 (enrdf_load_stackoverflow) 1973-05-25
FR2156305B1 (enrdf_load_stackoverflow) 1977-08-26
GB1383798A (en) 1974-02-12
DE2250055A1 (de) 1973-04-26
DE2250055C2 (de) 1982-11-18
JPS526283B2 (enrdf_load_stackoverflow) 1977-02-21
JPS4847504A (enrdf_load_stackoverflow) 1973-07-06

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