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
  • C11D1/38—Cationic compounds
  • C11D1/62—Quaternary ammonium compounds
• • C—CHEMISTRY; METALLURGY
  • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
  • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
  • C11D10/00—Compositions of detergents, not provided for by one single preceding group
  • C11D10/04—Compositions of detergents, not provided for by one single preceding group based on mixtures of surface-active non-soap compounds and soap
  • C11D10/047—Compositions of detergents, not provided for by one single preceding group based on mixtures of surface-active non-soap compounds and soap based on cationic surface-active compounds and soap
• • 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
  • C11D17/0047—Detergents in the form of bars or tablets
  • C11D17/006—Detergents in the form of bars or tablets containing mainly surfactants, but no builders, e.g. syndet bar

Definitions

• the present invention relates to improvements in soap compositions for use on the skin.
• the improvements reside in the formulation of soap compositions which contain certain nitrogen-based conditioning agents.
• These conditioning agents are salts wherein the cation moiety is a protonated fatty amine or a fatty quaternary ammonium ion and the anion moiety is the anion of a fatty acid soap or an anionic synthetic detergent.
• the conditioning agents are present at levels of from about 0.25% to 25% by weight in the composition.
• soap compositions There have been many attempts to alleviate the adverse skin effects caused by soap, by incorporating into soap compositions a variety of mildness additives. These have included vegetable oils, mineral oils, free fatty acids, fatty acid esters of polyols, and the like. While these materials tend to'alleviate the negative effects of soap upon the skin, there is a continuing need for improved skin conditioners to be used with soap.
• the object of the present invention is to provide soap compositions which are effective in cleansing the skin and are highly effective in alleviating the adverse effects on skin feel (especially external skin feel) which normally accompany the use of soap on the skin.
• the present invention encompasses skin cleansing compositions which comprise:-
• the soap component of the present compositions is an alkali metal (e.g., sodium or potassium) soap or mixture of soaps of fatty acids containing from about 8 to about 24, preferably from about 10 to 20 carbon atoms.
• the fatty acids used in making the soaps can be obtained from natural sources such as, for instance, plant or animal-derived glycerides (e.g., palm oil, coconut oil, babassu oil, soybean oil, castor oil, tallow, whale oil, fish oil, tallow, grease, lard and mixtures thereof).
• the fatty acids can also be synthetically prepared (e.g., by oxidation of petroleum stocks or by the Fischer-Tropsch process).
• Alkali metal soaps can be made by direct saponification of the fats and oils or by the neutralization of the free fatty acids which are prepared in a separate manufacturing process. Particularly useful are the sodium and potassium salts of the mixtures of fatty acids derived from coconut oil and tallow, i.e., sodium and potassium tallow and coconut soaps.
• tallow is used herein in connection with fatty acid mixtures which typically have an approximate carbon chain length distribution of 2.5% C 14 , 29% C 16' 23% C 18 , 2% palmitoleic, 41.5% oleic and 3% linoleic (the first three fatty acids listed are saturated). Other mixtures with similar distribution, such as the fatty acids derived from various animal tallows and lard, are also included within the term tallow.
• the tallow can also be hardened (i.e., hydrogenated) to convert part or all of the unsaturated fatty acid moieties to saturated fatty acid moieties.
• coconut oil refers to fatty acid mixtures which typically have an approximate carbon chain length distribution of about 8% C 8 , 7% C 10 , 48% C 12 , 17% C 14 , 9% C 16' 2 % C 18 , 7% oleic, and 2% linoleic (the first six fatty acids listed being saturated).
• the soap component is preferably either sodium soap or a mixture of sodium and potassium soap wherein the mixture contains no more than about 25% by weignt potassium soap.
• the total soap component comprises (a) from about 20% to 80% by weight of the soap component of a mixture containing soaps having from 8 to 14 carbon atoms and (b) from about 20% to 80% by weight of the soap component of soaps having from about 16 to 20 carbon atoms.
• Soaps having such preferred chain length distribution characteristics can be realized by utilizing mixtures of tallow and coconut fatty acids in tallow/coconut weight ratios varying between 90:10 and 50:50.
• the soap compositions herein can also contain free fatty acids having carbon chain lengths of from about 8 to 18.
• free fatty acids having carbon chain lengths of from about 8 to 18.
• the presence of such free fatty acids tends to improve the speed and volume of lathering of the composition and confers a creamy feel to the lather.
• free fatty acids are utilized in the compositions herein, they are generally present at levels of from about 5% to about 25% of the total amount of soap.
• the skin conditioning component of the present compositions is selcted from the group of compounds having the formulas: , and wherein R 1 , R 2 , R 3 and R 4 are each selected from the group consisting of hydrogen and aliphatic hydrocarbyl groups containing from 1 to about 24 carbon atoms, with at least one of R 1 , R 2 , R 3 and R 4 being an aliphatic hydrocarbyl group containing from about 8 to about 24 carbon atoms, wherein R 5 , R 6 , R 7 , R 8 and R 9 are each selected from the group consisting of hydrogen and aliphatic hydrocarbyl groups containing from 1 to about 24 carbon atoms with at least one of R5, R 6 , R 7 , R 8 and R 9 being an aliphatic hydrocarbyl group containing from about 8 to about 24 carbon atoms, wherein R 10 , R 11 , R 12 , R 13 , R14 and R15 are each selected from the group consisting of hydrogen and C1 to C24 aliphatic hydro
• These skin conditioning compounds are salts.
• the cation moiety of the salt is a protonated fatty amine or protonated imidazoline moiety or a quaternary ammonium or imidazolinium moiety.
• the cation is a protonated amine moiety. If all four "R" groups are hydrocarbyl groups, the cation is a quaternary ammonium moiety.
• Amines can be protonated by reacting them with an acidic material (e.g., HC1 or acetic acid).
• the resulting compound is a protonated amine salt, e.g., an amine hydrochloride or an amine acetate.
• Amines which are protonated to provide cation moieties for the present invention can be primary, secondary or tertiary amines, and must contain at least one aliphatic hydrocarbyl group of from 8 to 24 carbon atoms.
• Examples of such amines are dodecylamine, methyl octadecyl amine, dimethyl hexadecyl amine, didodecyl methyl amine, ethyl dodecyl octadecyl amine, N-tetradecyl, N'propyl-1,3-propane diamine, l-stearylamidoethyl-2-stearyl imidazoline and 1-ethylene bis(2-stearyl imidazoline).
• Examples of protonated amine salts formed from these amines are dodecylamine acetate, methyl octadecyl amine hydrochloride, dimethyl hexadecylamine hydrochloride, didodecyl methyl amine acetate,ethyl dodecyl octadecyl amine acetate, N-tetradecyl, N'-propyl-1,3-propane diamine dihydrochloride, I-stearylamidoethyl-2-stearyl imidazolinium hydrochloride and 1-ethylene bis(2-stearylimidazolinium)dihydrochloride.
• Such amine salts can be used to provide the protonated amine moiety which can serve as the cation of the skin conditioning agents of the present invention.
• the quaternary ammonium ions are the cations which are formed by quaternizing a tertiary aliphatic amine with an additional aliphatic group. This is accomplished by reacting a tertiary amine with an alkylating agent such as methyl chloride. For example, if didodecyl methyl amine is reacted with methyl chloride, the resulting quaternary ammonium salt is didodecyldimethylammonium chloride.
• Examples of specific quaternary ammonium salts which can be used to provide the quaternary ammonium cation moiety for the skin conditioning agents herein are didodecyldimethylammonium chloride, dodecyltrimethylammonium bromide, dihexadecyldimethylammonium acetate, N,N'-ditetradecyl-N, N,N',N'-tetramethyl-1,3-propyl diammonium dichloride, N,N'- distearyl-N,N,N',N'-tetramethyl-1,10-decyl diammonium diacetate, l-methyl-l-stearylamidoethyl-2-stearyl imidazolinium methyl sulfate and 1-ethylene bis(2-stearyl, 1-methylimidazolinium) dichloride.
• the conditioning agents of the present invention are prepared by simple reaction between a protonated amine or imidazoline salt (e.g., hydrochloride) or a quaternary ammonium or imidazolinium salt, and a fatty acid soap or an anionic synthetic detergent.
• a protonated amine or imidazoline salt e.g., hydrochloride
• a quaternary ammonium or imidazolinium salt e.g., a quaternary ammonium or imidazolinium salt
• the conditioning agent can also be prepared by reacting the free amine or imidazoline with a fatty acid (instead of a soap) or the acid form of the synthetic detergent (instead of the salt form of the detergent).
• a fatty acid instead of a soap
• the acid form of the synthetic detergent instead of the salt form of the detergent
• the anionic moiety of the skin conditioning agent herein can be the anion of a fatty acid soap (i.e., the radical wherein R 23 is a C 7 to C 23 aliphatic group) or the anion of an anionic synthetic detergent.
• Any anionic synthetic detergent can be used to provide the anion moiety for the skin conditioning agents herein.
• the most common types of anionic synthetic detergents are the water soluble salts (e.g., sodium, potassium, lithium or.ammonium) of organic sulfuric reaction products having in their molecule an aliphatic group containing from about 8 to about 24 carbon atoms, and a sulfonic or sulfuric acid ester radical.
• Synthetic detergents containing a C 8 to C 24 aliphatic group and having a carboxylic acid radical instead of a sulfonic or sulfuric acid ester radical can also be used.
• anionic synthetic detergents which can provide the anion moiety of the skin conditioning agents herein include the following:
• Examples of preferred skin conditioning agents of the present invention are stearylammonium laurate, ztearylammonium stearate, distearyldimethylammonium laurate, and distearyldimethylammonium stearate.
• the ratio of soap to conditioning agent in the compositions herein will be from about 1:1 to about 100:1, preferably from about 3:1 to about 20:1.
• the soap compositions of the present invention will normally contain water.
• the water content will be of the order of 50% to about 95%.
• the compositions are formulated into toilet bars, the water content will normally be of the order of 20% or less.
• antibacterial agents can be included in the present composition at levels of from about 0.5% to about 4%.
• Typical antibacterial agents which are suitable for use herein-are 3,4-di- and 3,4',5-tribromo- salicylanilides; 4,4'-dichloro-3-(trifluoromethyl) cabanilide; 3,4,4'-trichlorocarbanilide and mixtures of these materials.
• nonionic emollients can be included as additional skin conditioning agents in compositions of the present invention at levels up to about 40%, preferably at levels of from about 1% to about 25%.
• Such materials include, for example, mineral oils, paraffin .wax having a melting point of from about 100°F to about 170°F, fatty sorbitan esters (see U.S. Patent 3,988,255, Seiden, issued October 26, 1976 incorporated herein by reference), lanolin and lanolin derivatives, esters such as isopropyl myristate and triglycerides such as coconut oil or hydrogenated tallow.
• These nonionic-type skin conditioning agents appear to primarily contribute internal skin feel advantages to the compositions herein, whereas the aforedescribed protonated amine or quaternary salt conditioning agents appear to primarily contribute external skin feel advantages.
• Free fatty acid such as coconut oil fatty acid can be added to the compositions herein to improve the volume and quality (creaminess)of the lather produced by the compositions herein.
• perfumes, dyes and pigments can also be incorporated into compositions of the invention at levels up to about 5%.
• Perfumes are preferably used at levels of from about 0.5% to 3% and dyes and pigments are preferably used at levels of from about 0.001% to about 0.5%.
• Synthetic detergents can also be present in compositions herein.
• Preferred types of synthetic detergents are of the anionic or nonionic type.
• anionic synthetic detergents are the salts of organic sulfuric reaction products described in (1) through (5) hereinbefore.
• nonionic synthetic detergents are ethoxylated fatty alcohols (e.g., the reaction product of one mole of coconut fatty alcohol with from about 3 to 30 moles of ethylene oxide, the reaction product of one mole of coconut fatty acid with from about 3 to 30 moles of ethylene oxide and fatty acid amides such as coconut fatty acid monoethanolamide and stearic acid diethanolamide.
• compositions herein can be free of synthetic detergents.
• Synthetic detergents when present are normally employed at levels of from about 5% to about 400% by weight of the amount of soap in the compositions.
• Insoluble alkaline earth metal soaps such as calcium stearate and magnesium stearate can also be incorporated into compositions of the present invention at levels up to about 30%. These materials are particularly useful in toilet bars in which synthetic detergents are present in that they tend to reduce the relatively high solubility which such bars normally have. These alkaline earth metal soaps are not included within the term “soap” as otherwise used in this specification.
• the term “soap” as used herein refers to the alkali metal soaps.
• Lotions or creams can optionally contain thickeners or phase stabilizers such as carboxymethyl cellulose or xanthum gum.
• compositions of the present invention can be prepared in the form of toilet bars, or if desired, in the form of creams or lotions.
• the toilet bar is the most preferred form since this is the form of cleansing agent most commonly used to wash the skin.
• the toilet bars are made from a mixture of soaps derived from coconut oil and hydrogenated tallow, the ratio of coconut soap to tallow soap being from about 1:1 to about 1:4.
• the toilet soap compositions generally contain from about 5% to about 20% moisture.
• Toilet bars of the.present invention can be prepared in the conventional manner.
• Moisture-containing base soap can be admixed with the conditioning agent and other optional ingredients such as perfumes, dyes, etc., in an amalgamator, milled in the conventional manner under conventional conditions, and extruded into logs for cutting and stamping into toilet bars.
• the skin conditioning agent can be co-melted with the base soap and then cooled to solidify the mixture before introduction into the amalgamator.
• the conditioning agent is thoroughly mixed with an aqueous solution or dispersion of the soap.
• Toilet bars of the invention generally comprise from about 10% to about 90% (preferably from 60% to 90%) soap and from about 1% to about 25% (preferably from about 5% to about 15%) of the conditioning agents of the invention.
• Creams generally comprises from about 10% to about 45% soap and from about 0.5% to about 15% conditioning agent.
• Lotions generally comprises from about 3% to about 15% soap and from about .25% to about 5% conditioning agent. Creams generally contain from about 50% to about 75% water, and lotions about 75% to about 95% water.
• compositions of the invention can be used to prepare articles for cleansing the skin.
• These articles can comprise an absorbent paper or woven or nonwoven cloth which is impregnated with a composition of the invention.
• a nonwoven cloth can be impregnated with an aqueous solution of a toilet bar composition of the invention and then subjected to a drying process which drives off sufficient water to reduce the moisture content to about 20% or less of the composition thereby producing a cleansing article which is dry to the touch.
• the amount of composition on the substrate should be sufficient to produce a composition:s-ibstrate ratio of about 0.5:1 to 5:1. When it is used it is simply wetted with water and used in the usual manner of a wash cloth.
• compositions of the present invention are used in the conventional manner of skin cleansing agents, i.e., they are applied to the skin and then the skin is rinsed with water.
• the composition can be topically applied "as is” to the skin.
• a solution or dispersion of the composition is formed prior to application by wetting the surface of the bar or rubbing the bar onto a wet washcloth. The wet bar or the wet washcloth which contains a portion of the composition is then rubbed against the skin.
• the present invention also includes a method for cleansing and conditioning of the skin, said method comprising the steps of (1) applying to the skin a composition of the invention and (2) rinsing the skin with water.
• a toilet bar of the following composition was prepared:
• test product A panel of 27 women lathered the above bar soap composition (test product) on to a prewashed terry cloth and each woman washed one half of her face as she normally would. The product was then spray rinsed off the skin by a 10 second spray of 90-95°F water. The skin was pat dried with a paper towel. The second half of the face was then washed in the same manner with a bar of a control product which was made in the same way as described above but having the following composition:
• a lotion of the present invention is prepared as follows:
• This example illustrates an alternate method of preparing a toilet bar of the present invention.
• 11.9 lbs. of 50/50 tallow/coconut sodium soap noodles (81.5%-82.5% soap, 7% coconut fatty acid, 10-11% moisture and 0.5% NaCl) are added to an amalgamator.
• 0.2 lbs. of perfume and 1.07 lbs. of water and miscellaneous ingredients are then added and mixing is continued until the batch reaches a homogeneous color (about 5 minutes).
• the mixture is then transferred to a 3-roll soap mill (operating at about 95%), milled twice and stored overnight in an airtight container at 100°F.

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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)
• Cosmetics (AREA)

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Cited By (8)

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Citations (3)

• 1980
  • 1980-02-14 GR GR61211A patent/GR70683B/el unknown
  • 1980-02-15 EP EP80200128A patent/EP0015032A1/en not_active Withdrawn
  • 1980-02-15 PH PH23651A patent/PH16475A/en unknown
  • 1980-02-20 CA CA000346085A patent/CA1149745A/en not_active Expired
  • 1980-02-27 JP JP2392880A patent/JPS55149398A/ja active Pending

Patent Citations (3)

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