WO2000012670A1 - Bars comprising benefit agent and cationic polymer - Google Patents

Bars comprising benefit agent and cationic polymer Download PDF

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Publication number
WO2000012670A1
WO2000012670A1 PCT/EP1999/005826 EP9905826W WO0012670A1 WO 2000012670 A1 WO2000012670 A1 WO 2000012670A1 EP 9905826 W EP9905826 W EP 9905826W WO 0012670 A1 WO0012670 A1 WO 0012670A1
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WO
WIPO (PCT)
Prior art keywords
composition according
structurant
cationic polymer
surfactant
cationic
Prior art date
Application number
PCT/EP1999/005826
Other languages
English (en)
French (fr)
Inventor
Michael Joseph Fair
Michael Massaro
Harry Crookham
Gail Beth Rattinger
James Joseph Dalton
Terence James Farrell
Georgia Lynn Shafer
Original Assignee
Unilever Plc
Unilever Nv
Hindustan Lever Limited
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Priority claimed from US09/224,786 external-priority patent/US6057275A/en
Priority to EP99944360A priority Critical patent/EP1108005B1/en
Priority to MXPA01001978A priority patent/MXPA01001978A/es
Priority to HU0103331A priority patent/HUP0103331A3/hu
Priority to AU57324/99A priority patent/AU739677B2/en
Priority to CA002340706A priority patent/CA2340706A1/en
Application filed by Unilever Plc, Unilever Nv, Hindustan Lever Limited filed Critical Unilever Plc
Priority to BR9913251-6A priority patent/BR9913251A/pt
Priority to AT99944360T priority patent/ATE280215T1/de
Priority to PL99346301A priority patent/PL188602B1/pl
Priority to DE69921335T priority patent/DE69921335T2/de
Priority to JP2000571067A priority patent/JP2002525393A/ja
Publication of WO2000012670A1 publication Critical patent/WO2000012670A1/en

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Classifications

    • CCHEMISTRY; METALLURGY
    • C11ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11DDETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D3/00Other compounding ingredients of detergent compositions covered in group C11D1/00
    • C11D3/16Organic compounds
    • C11D3/20Organic compounds containing oxygen
    • C11D3/2075Carboxylic acids-salts thereof
    • C11D3/2079Monocarboxylic acids-salts thereof
    • CCHEMISTRY; METALLURGY
    • C11ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11DDETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D17/00Detergent materials or soaps characterised by their shape or physical properties
    • C11D17/0047Detergents in the form of bars or tablets
    • C11D17/006Detergents in the form of bars or tablets containing mainly surfactants, but no builders, e.g. syndet bar
    • CCHEMISTRY; METALLURGY
    • C11ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11DDETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D3/00Other compounding ingredients of detergent compositions covered in group C11D1/00
    • C11D3/16Organic compounds
    • C11D3/37Polymers
    • C11D3/3703Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • C11D3/3707Polyethers, e.g. polyalkyleneoxides
    • CCHEMISTRY; METALLURGY
    • C11ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11DDETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D3/00Other compounding ingredients of detergent compositions covered in group C11D1/00
    • C11D3/16Organic compounds
    • C11D3/37Polymers
    • C11D3/3746Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
    • C11D3/3769(Co)polymerised monomers containing nitrogen, e.g. carbonamides, nitriles or amines

Definitions

  • the present invention relates to bar compositions capable of delivering benefit agents to the skin. More particularly the invention relates to bars containing relatively large amounts of hydrophilic structurant (i.e. the ratio of hydrophilic to hydrophobic being at least 1:2, preferably greater than 40:60, more preferably at least 1:1 and most preferably above 1:1) and in which cationic polymer, particularly cationic polymer having minimum level of charge density, has been found to unexpectedly enhance deposition of benefit agent in such bars.
  • hydrophilic structurant i.e. the ratio of hydrophilic to hydrophobic being at least 1:2, preferably greater than 40:60, more preferably at least 1:1 and most preferably above 1:1
  • cationic polymer particularly cationic polymer having minimum level of charge density
  • Cationic polymers are well known in the art. For example in liquid cleansers, cationic hydrophilic polymers such as
  • Polymer JR from Americhol or Jaguar from Rhone Poulenc have been used to enhance delivery of benefit agents (as described in for example EP 93,602; WO 94/03152; and WO 94/03151) .
  • Cationic polymers have also been used in bar formulations.
  • U.S. Patent No. 3,761,418 to Parran, Jr. for example, teaches detergent composition (including bar soaps) containing water insoluble particulate substances such as antimicrobial agents and certain cationic polymers to enhance deposition and retention of such particulate substances.
  • bar soap formulations are used in the examples, all of the formulations are primarily structured with soap and/or fatty acid.
  • benefit agents oil/emollients
  • hydrophobic structurants would interfere with deposition of any such oils/emollients.
  • WO No. 95/26710 to Kacher et al . (assigned to P&G) teaches skin moisturizing and cleansing bar containing skin cleansing agent and lipid moisturizing agent.
  • a preferred optional ingredient is one or more cationic polymeric skin conditioning agent added to provide a tactile cue.
  • the bar is made of a rigid crystalline network structure consisting essentially of selected fatty acid soap material. The applicants have found such fatty acid soap material to be detrimental to deposition.
  • U.S. Patent No. 5,425,892 to Taneri et al teaches personal cleansing freezer bars comprising a skeleton structure of neutralized carboxylic acid soap.
  • the patent teaches polymeric skin feel aids, water soluble organics and oils.
  • the bars as noted, have a distinctive carboxylic acid structure differing from bars of the invention containing relatively large amounts of hydrophilic structurant .
  • Hydrophilic structured bars themselves are also taught, for example, in U.S. Patent No. 5,520,840 to Massaro et al . or U.S. Patent No. 5,540,854 to Fair et al . There is no teaching in these references, however, of cationic polymers, and no suggestion that such cationics could enhance deposition of oil/emollients in bars containing relatively large amounts of hydrophilic structurant. Further there is no teaching or suggestion in this or any other reference of a critical cationic to surfactant ratio above which deposition of oils/emollients is significantly enhanced or that cationics must have minimum level of charge density.
  • U.S. Patent No. 5,262,079 to Kacher et al teaches firm, mild neutral pH cleansing bars comprising 5-50% by wt . monocarboxylic fatty acids (which provides skeletal structure) , 20 to 65% bar firmness aid and 15% to 55% water.
  • the bars may contain optional polyols (0-40%) as "bar firmness aids" .
  • the bars are primarily fatty acid structured, and the only bar firmness aids exemplified are isethionate (i.e., they do not have minimum levels of hydrophilic to hydrophobic structurant) .
  • cationics disclosed are guar, quaternized guar etc., all of which have charge density below 0.007. There is thus no recognition that only cationic polymers having a minimum charge activity are adequate for purpose of the invention.
  • cationics i.e., cationic polymers of a minimum charge density level
  • hydrophilic structurant e.g., the ratio of hydrophilic to hydrophobic structurant being at least 1:2, preferably greater than 40:60, more preferably at least 1:1 and most preferably above 1:1; further that the total soap and hydrophobic structurant should exceed the hydrophilic structurant by no more than 10% by weight of the total composition
  • there is a minimum critical ratio of cationic polymer to surfactant at which deposition is remarkably enhanced it is critical that levels of surfactant, particularly anionic, not exceed certain ranges (lest deposition be affected) , and that minimum amounts of oil/emollient be used.
  • compositions comprising:
  • acyl isethionate or alkali metal lauryl ether sulfate e.g., acyl isethionate or alkali metal lauryl ether sulfate
  • the amount of insoluble structurant (c) and soap, if any, present exceeds the amount of hydrophilic structurant (b) by no more than 10% by wt . total bar composition; wherein the amount of cationic polymer (e) is such that ratio of cationic to surfactant is 0.06 to 1 to 1:1, more preferably 0.08:1 to 0.5:1; and wherein the charge density of cationic polymer (number of monovalent charges per repeat unit divided by molar mass of repeat unit) is greater than 0.007.
  • the present invention relates to relatively low active bars (e.g., 50% active, preferably less than 40%, more preferably 30% and less active) wherein there is present a relatively large amount of hydrophilic structurant (hydrophobic structurant and soap, if present, should comprise no more than about 10% by wt . more than amount of hydrophilic structurant) and which further comprises relatively large amount of oil/emollient (i.e., at least 2%).
  • hydrophilic structurant hydrophobic structurant and soap, if present, should comprise no more than about 10% by wt . more than amount of hydrophilic structurant
  • oil/emollient i.e., at least 2%
  • the bar is described in greater detail below.
  • the bars of the inventions should contain from about 10% to 50% by wt . more preferably 15 to 40% of a synthetic, non- soap surfactant .
  • Suitable surfactants are generally selected from the group consisting of anionic, nonionic, amphoteric, zwitterionic and/or cationic surfactants and mixtures thereof such as are well known in the art. More specifically, the surfactant system will generally comprise at least one anionic surfactant, a zwitterionic surfactant or, preferably mixtures of anionic or anionics and zwitterionic surfactant .
  • the anionic surfactant which may be used may be aliphatic sulfonates, such as a primary alkane (e.g., C 8 -C 22 ) sulfonate, primary alkane (e.g., C 8 -C 22 ) disulfonate, C 8 -C 22 alkene sulfonate, C 8 -C 22 hydroxyalkane sulfonate or alkyl glyceryl ether sulfonate (AGS) ; or aromatic sulfonates such as alkyl benzene sulfonate.
  • a primary alkane e.g., C 8 -C 22
  • primary alkane e.g., C 8 -C 22
  • disulfonate C 8 -C 22 alkene sulfonate
  • C 8 -C 22 hydroxyalkane sulfonate C 8 -C 22 hydroxyalkane sulfonate or al
  • the anionic may also be an alkyl sulfate (e.g., C 12 -C 18 alkyl sulfate) or alkyl ether sulfate (including alkyl glyceryl ether sulfates) .
  • alkyl ether sulfates are those having the formula:
  • R is an alkyl or alkenyl having 8 to 18 carbons, preferably 12 to 18 carbons, n has an average value of greater than 1.0, preferably greater than 3; and M is a solubilizing cation such as sodium, potassium, ammonium or substituted ammonium. Ammonium and sodium laurel ether sulfates are preferred.
  • the anionic may also be alkyl sulfosuccinates (including mono and dialkyl , e.g., C 6 -C 22 sulfosuccinates) ; alkyl and acyl taurates, alkyl and acyl sarcosinates, sulfoacetates, C 8 _c 22 alkyl phosphates and phosphates, alkyl phosphate esters and alkoxyl alkyl phosphate esters, acyl lactates, C 8 -C 22 monoalkyl succinates and maleates, sulphoacetates, alkyl glucosides and acyl isethionates .
  • alkyl sulfosuccinates including mono and dialkyl , e.g., C 6 -C 22 sulfosuccinates
  • alkyl and acyl taurates alkyl and acyl sarcosinates, sulfo
  • Sulfosuccinates may be monoalkyl sulfosuccinates having the formula :
  • R ranges from C 8 -C 22 alkyl and M is a solubilizing cation.
  • Sarcosinates are generally indicated by the formula RCON(CH 3 ) CH 2 C0 2 M, wherein R ranges from C 8 -C 2 o alkyl and M is a solubilizing cation.
  • Taurates are generally identified by formula
  • R ranges from C 8 -C 20 alkyl
  • R ranges from C 1 -C 4 alkyl
  • M is a solubilizing cation.
  • Particularly preferred are the Cs-Cis acyl isethionates .
  • esters are prepared by reaction between alkali metal isethionate with mixed aliphatic fatty acids having from 6 to 18 carbon atoms and an iodine value of less than 20. At least 75% of the mixed fatty acids have from 12 to 18 carbon atoms and up to 25% have from 6 to 10 carbon atoms.
  • Acyl isethionates when present, will generally range from about 10% to about 50% by weight of the total bar composition. Preferably, this component is present from about 20% to about 40%.
  • the acyl isethionate may be an alkoxylated isethionate such as is described in Ilardi et al . , U.S. Patent No. 5,393,466, hereby incorporated by reference.
  • Anionic surfactant may also be a "soap" .
  • soap alkali metal salts of aliphatic alkane- or alkene monocarboxylic acids, more generally known as C 12 -C 22 alkyl fatty acids. Sodium and potassium salts are preferable.
  • a preferred soap is a mixture of about 15% to about 45% coconut oil and about 55% to about 85% tallow.
  • the soaps may contain unsaturation in accordance with commercially acceptable standards. Excessive unsaturation is normally avoided.
  • the anionic component will comprise from about 10% to 50% of the bar composition.
  • Amphoteric detergents which may be used in this invention include at least one acid group. This may be a carboxylic or a sulphonic acid group. They include quaternary nitrogen and therefore are quaternary amido acids. They should generally include an alkyl or alkenyl group of 7 to 18 carbon atoms. They will usually comply with an overall structural formula:
  • R is alkyl or alkenyl of 7 to 18 carbon atoms
  • R are each independently alkyl, hydroxyalkyl or carboxyalkyl of 1 to 3 carbon atoms; n is 2 to 4; m is 0 to 1; x is alkylene of 1 to 3 carbon atoms optionally substituted with hydroxyl , and y is -CO 2 - or -SO 3 - .
  • Suitable amphoteric detergents within the above general formula include simple betaines of formula:
  • R is alkyl or alkenyl of 7 to 18 carbons
  • R and R are independently alkyl, hydroxyalkyl or i carboxylalkyl of 1 to 3 carbons.
  • R may in particular be a mixture of C 12 and C 14 alkyl groups derived from coconut so that at least half, preferably at least three quarters of
  • R have 10 to 14 carbon atoms.
  • R and R are preferably methyl .
  • amphoteric detergent is a sulphobetaine of formula:
  • Amphoteric generally comprises 1% to 10% of the bar composition.
  • surfactants i.e., nonionics, cationics
  • nonionics i.e., nonionics, cationics
  • cationics i.e., nonionics, cationics
  • Nonionic surfactants include in particular the reaction products of compounds having a hydrophobic group and a reactive hydrogen atom, for example, aliphatic alcohols, acids, amides or alkyl phenols with alkylene oxides, especially ethylene oxide either alone or with propylene oxide.
  • Specific nonionic detergent compounds are alkyl (Cg- C22) phenols-ethylene oxide condensates, the condensation products of aliphatic (Cs-Cis) primary or secondary linear or branched alcohols with ethylene oxide, and products made by condensation of ethylene oxide with the reaction products of propylene oxide and ethylenediamine .
  • Other so-called nonionic detergent compounds include long chain tertiary amine oxides, long chain tertiary phosphine oxides and dialkyl sulphoxides .
  • the nonionic may also be a sugar amide, such as a polysaccharide amide.
  • the surfactant may be one of the lactobionamides described in U.S. Patent No.
  • Patent No. 5,312,954 to Letton et al . hereby incorporated into the subject application by reference.
  • cationic detergents are the quaternary ammonium compounds such as alkyldimethylammonium halogenides.
  • a preferred composition comprises 10 to 50% acyl isethionate and 1% to 10% betaine .
  • hydrophilic structurant e.g., polyalkylene glycol
  • This component should comprise greater than 10% by wt . to 40%, preferably greater than 15% to 35% by wt . of the bar composition.
  • the structurant has a melting point of 40° to 100°C, preferably 45°C to 100°C, more preferably 50° to 90°C. Generally these structurants will be at least 10% water soluble at room temperature.
  • water soluble structurant (b) Materials which are envisaged as the water soluble structurant (b) are moderately high molecular weight polyalkylene oxides of appropriate melting point and in particular polyethylene glycols or mixtures thereof.
  • Polyethylene glycols which may be used may have a molecular weight in the range 1,500-20,000.
  • (R) Carbide's Carbowax PEG-8,000) represents a distribution of molecular weights.
  • PEG 8,000 for example, has an average MW range of 7,000-9,000
  • PEG 300 has an average MW range from 285 to 315.
  • the average MW of the product can be anywhere between the low and high value, and there may still be a good portion of the material with MW below the low value and above the high value.
  • polyalkylene glycol e.g., polyethylene glycol
  • a molecular weight in the range from 50,000 to 500,000, especially molecular weights of around 100,000.
  • polyethylene glycols have- been found to improve the wear rate of the bars. It is believed that this is because their long polymer chains remain entangled even when the bar composition is wetted during use .
  • the quantity is preferably from 1% to 5%, more preferably from 1% or 1.5% to 4% or 4.5% by weight of the composition.
  • these materials will generally be used jointly with a larger quantity of other water soluble structurant (b) such as the above mentioned polyethylene glycol of molecular weight 1,500 to 10,000.
  • polyethylene oxide polypropylene oxide block copolymers melt at temperatures in the required range of 40 to 100°C and may be used as part or all of the water soluble structurant (b) .
  • block copolymers in which polyethylene oxide provides at least 40% by weight of the block copolymer.
  • Such block copolymers may be used, in mixtures with polyethylene glycol or other polyethylene glycol water soluble structurant.
  • water soluble adjuvant fillers may be used in combination with the water soluble structurant.
  • the water insoluble structurants are also required to have a melting point in the range 40-100°C, more preferably at least 50°C, notably 50°C to 90°C.
  • Suitable materials which are particularly envisaged are fatty acids, particularly those having a carbon chain of 12 to 24 carbon atoms. Examples are lauric, myristic, palmitic, stearic, arachidonic and behenic acids and mixtures thereof. Sources of these fatty acids are coconut, topped coconut, palm, palm kernel, babassu and tallow fatty acids and partially or fully hardened fatty acids or distilled fatty acids.
  • Other suitable water insoluble structurants include alkanols of 8 to 20 carbon atoms, particularly cetyl alcohol. These materials generally have a water solubility of less than 5g/litre at 20°C.
  • the relative proportions of the water soluble structurants and water insoluble structurants govern the rate at which the bar wears during use .
  • the presence of the water insoluble structurant tends to delay dissolution of the bar when exposed to water during use and hence retard the rate of wear.
  • insoluble structurant will comprise 5 to 20% by wt . of the composition.
  • the amount of water insoluble structurant (c) should not exceed the amount of hydrophilic structurant (b) plus any soap which may be present by more than about 10% by wt . While not wishing to be bound by theory, this is believed to be so because when there is too much soap and/or hydrophilic structurant, level of deposition is reduced.
  • the benefit agent of the compositions of the invention is included in the compositions to moisturize, condition and/or protect the skin.
  • skin skin corneum
  • the benefit agent of the compositions of the invention is included in the compositions to moisturize, condition and/or protect the skin.
  • “benefit agent” is meant a substance that softens the skin (stratum corneum) and keeps it soft by retarding the decrease of its water content and/or protects the skin.
  • Preferred benefit agents include:
  • silicone oils, gums and modifications thereof such as linear and cyclic polydimethylsiloxanes, amino, alkyl alkylaryl and aryl silicone oils
  • fats and oils including natural fats and oils such as jojoba, soybean, sunflower, rice bran, avocado, almond, olive, sesame, persic, castor, coconut, mink oils; cacao fat, beef tallow, lard; hardened oils obtained by hydrogenating the aforementioned oils; and synthetic mono, di and triglycerides such as myristic acid glyceride and 2- ethylhexanoic acid glyceride;
  • waxes such as carnauba, spermaceti, beeswax, lanolin and derivatives thereof;
  • hydrophobic plant extracts (d) hydrophobic plant extracts; (e) hydrocarbons such as liquid paraffins, petroleum jelly, microcrystalline wax, ceresin, squalene, squalane, and mineral oil;
  • higher fatty acids such as lauric, myristic, palmitic, stearic, behenic, oleic, linoleic linolenic, lanolic, isostearic and poly unsaturated fatty acids (PUFA) acids;
  • PUFA poly unsaturated fatty acids
  • esters such as cetyl octanoate, myristyl lactate, cetyl lactate, isopropyl myristate, myristyl myristate, isopropyl palmitate, isopropyl adipate, butyl stearate, decyl oleate, cholesterol isostearate, glycerol monostearate, glycerol distearate, glycerol tristearate, alkyl lactate (for example lauryl lactate), alkyl citrate and alkyl tartrate; (i) essential oils such as fish oils, mentha, jasmine, camphor, white cedar, bitter orange peel, ryu, turpentine, cinnamon, bergamont, citrus unshiu, calamus, pine, lavender, bay, clove, hiba, eucalyptus, lemon, starflower, thyme, peppermint, rose, sage, menthol, cineole, eugen
  • lipids such as cholesterol, ceramides, sucrose esters and pseudo-ceramides as described in European Patent application No. 556,957;
  • vitamins such as vitamin A and E, and vitamin alkyl esters, including those vitamin C alkyl esters;
  • sunscreens such as octyl methoxyl cinnamate (Parsol MCX) and butyl methoxy benzoylmethane (Parsol 1789) ;
  • phospholipids such as glycerin, propylene glycol and sorbitol;
  • the benefit agent may be incorporated in the compositions of the invention in a carrier.
  • Such benefit agents include lipids; alkyl lactates; sunscreens; esters such as isopropyl palmitate and isopropyl myristate; and vitamins.
  • the carrier can, for example, be a silicone or hydrocarbon oil which is not solubilized/micellized by the surface active phase and in which the benefit agent is relatively soluble.
  • Particularly preferred benefit agents include silicone oils, gums and modification thereof, esters such as isopropyl palmitate and myristate and alkyl lactates, and vegetable oils such as sunflower seed oil.
  • the benefit agent can be provided in the form of an emulsion.
  • the benefit agent of the invention may also function as a carrier to deliver efficacy agents to skin treated with the compositions of the invention.
  • This route is particularly useful for delivering efficacy agents which are difficult to deposit onto the skin or those which suffer detrimental interactions with other components in the composition.
  • the carrier is as often a silicone or hydrocarbon oil which is not solubilized/micellized by the surface active phase and in which the efficacy agent is relatively soluble.
  • efficacy agents include antiviral agents; hydroxycaprylic acids; pyrrolidone; carboxylic acids; 3 , 4 , 4 ' -trichlorocarbanilide; benzoyl peroxide; perfumes; essential oils; germicides and insect repellents such as 2 ,4 , 4 ' -trichloro-2 ' -hydroxydiphenyl ether (Irgasan DP300) ; salicylic acid; willow extract, N,N-dimethyl m- toluamide (DEET) ; and mixtures thereof.
  • antiviral agents include antiviral agents; hydroxycaprylic acids; pyrrolidone; carboxylic acids; 3 , 4 , 4 ' -trichlorocarbanilide; benzoyl peroxide; perfumes; essential oils; germicides and insect repellents such as 2 ,4 , 4 ' -trichloro-2 ' -hydroxydiphenyl ether (Irgasan DP
  • the benefit agent comprises 2 to 40%, preferably 5 to 20% by wt . of the composition.
  • the cationic polymer is a water soluble cationic polymer or copolymers having a molecular weight from about 1,000 to 2,000,000 and a high cationic charge density.
  • the cationic charge density should be at least 0.007 and higher where cationic charge density is defined as number of monovalent charges per repeat unit divided by the molar mass of repeat unit.
  • a Jaguar type cationic such as Jaguar C14S (R) (such as used in example RR of Kacher et al .
  • (R) propyl] urea dichloride (Mirapol A15 ) which has charge density of 0.00661.
  • dimethyldiallylammonium chloride (Mirquat 100 (R) ) has density of 0.00793 and is within the invention.
  • a cationic polymer such as dimethyldiallylammonium chloride can be prepared at concentrations of 40% (60% water)
  • the low charge density quaternized guar cationic polymer (Tradename Jaguar C14s) exemplified by Kacher et al . can only be prepared at concentrations of approximately 3% (97% water) and are not practical on a commercial scale.
  • Exemplary cationic polymers which may be used according to the invention include Salcare w type polymers from Allied
  • Those cationic polymers which are generally not applicable according to the invention are the high molecular weight, low charge density polymers such as Polymer JR-400 from
  • Amerchol and cationic polysaccharides of the cationic guar gum class such as Jaguar C14S from Rhone-Poulenc .
  • ratio of cationic to surfactant is 0.06:1 to 1:1, more preferably 0.08 to 1 to 0.5 to 1.
  • ratio of hydrophilic structurant to total of soap and hydrophobic structurant should be at least 1:2, preferably 40:60, more preferably at least 1:1 and most preferably greater than 1:1.
  • the term comprises or comprising is to be understood to specify the presence of stated features integers, steps, components etc., but not to preclude the presence or addition of one or more features, integers, steps, components or groups thereof .
  • Sodium cocoyl isethionate was supplied by Lever Baltimore, Polyethylene glycol (PEG 8000) was supplied by Union Carbide, and Merquat 100 (cationic polymer) was supplied by Calgon Corporation.
  • Polydimethylsiloxane (PDMS) with viscosity of 60,000 cs was from Dow Corning, Maltodextrin was from Grain Processing Corp., and the cocoamidopropyl betaine was from Goldschmidt Palmitic, stearic acid, and sodium stearate were supplied by Unichema.
  • the formulation was dropped onto a heated applicator roll and then was chipped over a chill roll.
  • the chill roll chips were plodded in a Weber Seelander duplex refiner with screw speed at -20 rpm.
  • the nose cone of the plodder was heated to 45-50°C.
  • the cut billets were stamped using a Weber Seelander L4 hydraulic press with a nylon, pillow-shaped die in place.
  • compositions e.g., high acyl isethionate bars structured with fatty acid
  • soap based compositions results in negligible deposition of the benefit agent.
  • High surfactant levels e.g., 60%
  • insoluble structurants e.g., fatty acid
  • hydrophilic structured bars such as those taught in U.S. Patent No. 5,520,840 to Massaro et al . result in little deposition.
  • hydrophilic structurant bars In order to study effect of cationic polymer in such low active, hydrophilic structurant bars, however, the following compositions were prepared.
  • compositions were prepared by mixing ingredients at temperature sufficiently high to provide mix, cooling on chill roll to form chips/flakes, extruding, cutting and stamping. Compositions made are set forth in Table 1 above.
  • Attenuated Total Reflectance Fourier Transform Infrared Spectroscopy was the analytical technique used to measure silicone deposition.
  • the test bar is wetted and rotated ten times in the hand, the inner forearm is then wetted and the bar is rubbed ten times on the forearm. This is followed by a thirty second wash and a fifteen second rinse.
  • the arm is then dried and an infrared scan of the inner forearm is obtained.
  • the silicone is quantified by integrating the absorption band between 770cm and 835cm . This is plotted on a standard
  • the amount of oil deposited on the skin appears to be a function of the cationic polymer to surfactant ratio. Specifically, a minimum ratio of 0.06 seems to be required. In the absence of polymer, virtually no silicone is detected on the skin from the bar prototypes. When the polymer : surfactant ratio is increased, a considerable increase in deposition is observed.
  • ratio cationic/surfactant 0.083
  • ratio cationic/surfactant 0.0625
  • Example 6 contained 30% sodium cocoyl isethionate (SCI) with 2.5% Merquat and 10% PDMS. In Example, the SCI was increased to 40%. The Merquat and PDMS levels were not changed.
  • SCI sodium cocoyl isethionate
  • Table 4 also compares in-vivo deposition from the bar prototypes (Examples 6 & 7) to a liquid body wash (Example 8) . As noted, significantly higher levels of oil are deposited on the skin from the bar prototypes.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Wood Science & Technology (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Emergency Medicine (AREA)
  • Cosmetics (AREA)
  • Detergent Compositions (AREA)
  • Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
  • Compositions Of Macromolecular Compounds (AREA)
  • Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)
PCT/EP1999/005826 1998-08-26 1999-08-10 Bars comprising benefit agent and cationic polymer WO2000012670A1 (en)

Priority Applications (10)

Application Number Priority Date Filing Date Title
JP2000571067A JP2002525393A (ja) 1998-08-26 1999-08-10 益剤およびカチオン性ポリマーを含んでなるバー
MXPA01001978A MXPA01001978A (es) 1998-08-26 1999-08-10 Barras comprendiendo agente de beneficio y polimero cationico.
HU0103331A HUP0103331A3 (en) 1998-08-26 1999-08-10 Bar composition comprising cationic polymer
AU57324/99A AU739677B2 (en) 1998-08-26 1999-08-10 Bars comprising benefit agent and cationic polymer
CA002340706A CA2340706A1 (en) 1998-08-26 1999-08-10 Bars comprising benefit agent and cationic polymer
EP99944360A EP1108005B1 (en) 1998-08-26 1999-08-10 Bars comprising benefit agent and cationic polymer
BR9913251-6A BR9913251A (pt) 1998-08-26 1999-08-10 Composição em barra
AT99944360T ATE280215T1 (de) 1998-08-26 1999-08-10 Reinigungsmittelstücke enthaltend einen wirkstoffe und ein kationisches polymer
PL99346301A PL188602B1 (pl) 1998-08-26 1999-08-10 Kompozycja kostki
DE69921335T DE69921335T2 (de) 1998-08-26 1999-08-10 Reinigungsmittelstücke enthaltend einen wirkstoffe und ein kationisches polymer

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
US14031298A 1998-08-26 1998-08-26
US09/140,312 1998-08-26
US09/224,786 1999-01-04
US09/224,786 US6057275A (en) 1998-08-26 1999-01-04 Bars comprising benefit agent and cationic polymer

Publications (1)

Publication Number Publication Date
WO2000012670A1 true WO2000012670A1 (en) 2000-03-09

Family

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Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/EP1999/005826 WO2000012670A1 (en) 1998-08-26 1999-08-10 Bars comprising benefit agent and cationic polymer

Country Status (15)

Country Link
EP (1) EP1108005B1 (zh)
JP (1) JP2002525393A (zh)
CN (1) CN1250698C (zh)
AT (1) ATE280215T1 (zh)
AU (1) AU739677B2 (zh)
BR (1) BR9913251A (zh)
CA (1) CA2340706A1 (zh)
CZ (1) CZ297811B6 (zh)
DE (1) DE69921335T2 (zh)
ES (1) ES2232171T3 (zh)
HU (1) HUP0103331A3 (zh)
MX (1) MXPA01001978A (zh)
PL (1) PL188602B1 (zh)
RU (1) RU2223309C2 (zh)
WO (1) WO2000012670A1 (zh)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2833186B1 (fr) * 2001-12-12 2004-01-23 Rhodia Chimie Sa Utilisation de copolymeres cationiques a blocs comme aide au depot d'emulsions simples ou multiples
US7015179B1 (en) * 2004-12-22 2006-03-21 Unilever Home & Personal Care Usa Reduced odor toilet bar composition
GB2576336B (en) * 2018-08-14 2020-12-16 Thos Bentley & Son Ltd Improvements in relation to the manufacture of personal cleansing compositions

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1994021778A1 (en) * 1993-03-16 1994-09-29 Unilever Plc Synthetic detergent bar and manufacture thereof
WO1997034992A1 (en) * 1996-03-18 1997-09-25 Unilever Plc Bar composition comprising copolymer mildness actives
US5770556A (en) * 1997-03-21 1998-06-23 Lever Brothers Company, Division Of Conopco, Inc. Process for making bar compositions having enhanced deposition of benefit agent comprising use of specific spray dryable adjuvant powders

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1994021778A1 (en) * 1993-03-16 1994-09-29 Unilever Plc Synthetic detergent bar and manufacture thereof
WO1997034992A1 (en) * 1996-03-18 1997-09-25 Unilever Plc Bar composition comprising copolymer mildness actives
US5770556A (en) * 1997-03-21 1998-06-23 Lever Brothers Company, Division Of Conopco, Inc. Process for making bar compositions having enhanced deposition of benefit agent comprising use of specific spray dryable adjuvant powders

Also Published As

Publication number Publication date
CZ2001716A3 (cs) 2002-03-13
DE69921335T2 (de) 2005-03-17
HUP0103331A3 (en) 2002-08-28
CN1250698C (zh) 2006-04-12
JP2002525393A (ja) 2002-08-13
CZ297811B6 (cs) 2007-04-04
PL346301A1 (en) 2002-01-28
CA2340706A1 (en) 2000-03-09
HUP0103331A2 (hu) 2002-01-28
DE69921335D1 (de) 2004-11-25
CN1324396A (zh) 2001-11-28
EP1108005A1 (en) 2001-06-20
EP1108005B1 (en) 2004-10-20
BR9913251A (pt) 2001-05-22
ES2232171T3 (es) 2005-05-16
MXPA01001978A (es) 2005-07-25
AU5732499A (en) 2000-03-21
RU2223309C2 (ru) 2004-02-10
PL188602B1 (pl) 2005-02-28
ATE280215T1 (de) 2004-11-15
AU739677B2 (en) 2001-10-18

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