EP0794763A4 - Compositions a base de silicone - Google Patents

Compositions a base de silicone

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Publication number
EP0794763A4
EP0794763A4 EP95943372A EP95943372A EP0794763A4 EP 0794763 A4 EP0794763 A4 EP 0794763A4 EP 95943372 A EP95943372 A EP 95943372A EP 95943372 A EP95943372 A EP 95943372A EP 0794763 A4 EP0794763 A4 EP 0794763A4
Authority
EP
European Patent Office
Prior art keywords
oil
acetate
methyl
aminoalkylsilicone
acid
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Withdrawn
Application number
EP95943372A
Other languages
German (de)
English (en)
Other versions
EP0794763A1 (fr
Inventor
Iain Allan Hughes
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.)
Procter and Gamble Co
Original Assignee
Procter and Gamble Co
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Filing date
Publication date
Application filed by Procter and Gamble Co filed Critical Procter and Gamble Co
Publication of EP0794763A1 publication Critical patent/EP0794763A1/fr
Publication of EP0794763A4 publication Critical patent/EP0794763A4/fr
Withdrawn legal-status Critical Current

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Classifications

    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q13/00—Formulations or additives for perfume preparations
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
    • A23L27/00—Spices; Flavouring agents or condiments; Artificial sweetening agents; Table salts; Dietetic salt substitutes; Preparation or treatment thereof
    • A23L27/70—Fixation, conservation, or encapsulation of flavouring agents
    • A23L27/74—Fixation, conservation, or encapsulation of flavouring agents with a synthetic polymer matrix or excipient, e.g. vinylic, acrylic polymers
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/02—Cosmetics or similar toiletry preparations characterised by special physical form
    • 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
    • A61K8/19—Cosmetics or similar toiletry preparations characterised by the composition containing inorganic ingredients
    • A61K8/22—Peroxides; Oxygen; Ozone
    • 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
    • A61K8/58—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing atoms other than carbon, hydrogen, halogen, oxygen, nitrogen, sulfur or phosphorus
    • A61K8/585—Organosilicon compounds
    • 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
    • A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
    • A61K8/84—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds obtained by reactions otherwise than those involving only carbon-carbon unsaturated bonds
    • A61K8/89—Polysiloxanes
    • A61K8/896—Polysiloxanes containing atoms other than silicon, carbon, oxygen and hydrogen, e.g. dimethicone copolyol phosphate
    • A61K8/898—Polysiloxanes containing atoms other than silicon, carbon, oxygen and hydrogen, e.g. dimethicone copolyol phosphate containing nitrogen, e.g. amodimethicone, trimethyl silyl amodimethicone or dimethicone propyl PG-betaine
    • 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
    • A61K8/92—Oils, fats or waxes; Derivatives thereof, e.g. hydrogenation products thereof
    • A61K8/922—Oils, fats or waxes; Derivatives thereof, e.g. hydrogenation products thereof of vegetable origin
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
    • A61L9/00—Disinfection, sterilisation or deodorisation of air
    • A61L9/01—Deodorant compositions
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q11/00—Preparations for care of the teeth, of the oral cavity or of dentures; Dentifrices, e.g. toothpastes; Mouth rinses
    • A61Q11/02—Preparations for deodorising, bleaching or disinfecting dentures
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
    • A61K2800/20—Chemical, physico-chemical or functional or structural properties of the composition as a whole
    • A61K2800/22—Gas releasing
    • A61K2800/222—Effervescent
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
    • A61K2800/20—Chemical, physico-chemical or functional or structural properties of the composition as a whole
    • A61K2800/24—Thermal properties
    • A61K2800/244—Endothermic; Cooling; Cooling sensation

Definitions

  • the present invention relates to silicone-containing compositions and to use thereof in various household products such as personal care products, laundry and household cleaners, bleaching compositions and the like.
  • silicone-containing lipophilic compositions based on flavorants, perfumes, coolants or antimicrobial agents as lipophile and which display improved residuality, impact and/or efficacy on surfaces treated therewith, for example teeth, dentures, skin, hair, laundry, dishware, working surfaces and the like.
  • silicone-containing bleach compositions which additionally contain bleach- sensitive ingredients such as perfumes, flavorants and the like and which display improved stability.
  • Lipophilic compositions such as flavor, perfume, coolant and disinfectant compositions are widely used either directly or in a variety of household products inclusive of cosmetics, oral and denture compositions, bleach, dishwashing, hard surface cleaning and laundry detergent products, etc.
  • a common problem encountered with lipophilic compositions is that of improving surface substantivity or residuality of the lipophilic component. It would be desirable in many if not most household applications to enhance the surface residuality of the lipophile in order, for example, to provide increased flavor or perfume impact or increased antimicrobial efficacy.
  • Modern dental hygiene and denture preparations typically contain antiplaque and/or antitartar agents, as well as antimicrobial agents and flavorants.
  • Antimicrobial action could affect plaque formation by either reducing the number of bacteria in the mouth/dentures or by killing those bacteria trapped in the film to prevent further growth and metabolism.
  • Flavorants may alleviate the problem of bad breath via a deodorizing action.
  • Some antimicrobial agents, e.g. menthol may, also serve as breath deodorizers.
  • the efficacy of antimicrobial agents depends largely on their intraoral/denture retention, particularly their retention on the surface of the teeth or dentures where plaque is formed.
  • a typical disadvantage of known dental preparations is that only a relatively short time during which the teeth are being cleaned or the mouth is being rinsed is available for antimicrobial agents in the preparations to take effect.
  • the problem is compounded by the fact that dentifrice preparations are used infrequently; most are used once or, perhaps, twice daily. Consequently, the long time period between brushings for a majority of the population provides optimum plaque forming conditions.
  • Laundry detergents for example, would benefit by increasing perfume substantivity on fabrics so as to provide increased perfume impact on clothing after laundering or during use. Increased antimicrobial substantivity would also be beneficial from the viewpoint of reducing malodors associated with sweat or other soils. Enhanced perfume substantivity would also be valuable in fine fragrance and perfumed cosmetics. Enhanced coolant substantivity, on the other hand, would be beneficial in cough cold products.
  • GB-A- 689,679 discloses a mouthwash containing an organopolysiloxane for preventing adhesion of, or for removing tars, stains, tartar and food particles from the teeth.
  • the mouthwash may include antiseptic compounds, such as thymol, and flavoring and perfuming agents.
  • US- A-2, 806,814 discloses dental preparations including, in combination, a higher aliphatic acyl amide of an amino carboxylic acid compound as an active and a silicone compound.
  • silicone compounds have been proposed for prevention of adhesion or to facilitate the removal of tars, stains, tartar and the like from teeth.
  • the silicone compound is said to act as a synergist in improving the antibacterial and acid inhibiting activity of the active ingredient.
  • Dimethyl polysiloxanes are said to be particularly effective. Flavoring oils and/or menthol may be included.
  • US-A-3624120 discloses quaternary ammonium salts of cyclic siloxane polymers for use as cationic surfactants, bactericides and as anticariogenic agents.
  • the present invention provides a flavor, perfume, coolant, antimicrobial or other lipophilic composition having improved surface- substantivity, impact and/or efficacy.
  • the invention further provides a bleach composition comprising an inorganic persalt bleaching agent, and a lipophilic compound such as a flavorant and/or perfume and which has improved stability.
  • a flavor, perfume, coolant, antimicrobial or other lipophilic composition comprising an aminoalkylsilicone having an aminoalkylsiloxane content of from about 0.1 % -2% on a repeating unit basis.
  • the invention also relates to the use of an aminoalkylsilicone with a lipophile selected from flavorants, perfumes, physiological coolants, antimicrobial agents and mixtures thereof to provide improved surface residuality, wherein the aminoalkylsilicone is selected from aminoalkylsilicones having an aminoalkylsiloxane content of from about 0.1 % -2% on a repeating unit basis.
  • a bleach composition comprising an inorganic persalt bleaching agent, a lipophile selected from flavorants, perfumes, physiological coolants, antimicrobial agents and mixtures thereof, and an aminoalkylsilicone having an aminoalkylsiloxane content of from about 0.1 % -2% on a repeating unit basis.
  • the invention also relates to the use of an aminoalkylsilicone with an inorganic persalt bleaching agent and a lipophile selected from flavorants, perfumes, physiological coolants, antimicrobial agents and mixtures thereof to provide improved lipophile stability, wherein the aminoalkylsilicone is selected from aminoalkylsilicones having an aminoalkylsiloxane content of from about 0.1 % -2% on a repeating unit basis.
  • compositions of the invention thus comprise an aminoalkylsilicone antiplaque agent and a lipophile selected from flavorants, perfumes, physiological coolants, antimicrobial agents and mixtures thereof.
  • Other compositions of the invention take the form of bleach and/or detergent compositions which comprise the aminoalkylsilicone antiplaque agent and lipophile.
  • aminoalkylsilicone is selected from noncyclic, hydrophobic aminoalkysilicones having a formula comprising two basic units:
  • Rl and R ⁇ are independently selected from H ,alkyl and alkenyl of about 1 to about 10 carbons optionally substituted with fluoro or cyano groups, hydroxy, alkoxy, and acetoxy, for example, wherein Rl and R ⁇ are independently selected from methyl, ethyl, phenyl, vinyl, trifluoropropyl and cyanopropyl, and R is
  • R3 is a divalent alkylene of about 1-20, preferably about 3-5 carbon atoms optionally substituted or interrupted by O atoms
  • R 4 , R ⁇ and R6 which may be the same or different are selected from H, alkyl of about 1-20, preferably about 1-10, more preferably about 1-4 carbons optionally substituted or interrupted by N and/or O atoms
  • X" is a monovalent anion such as halide, hydroxide, and tosylate, said aminoalkylsilicone including from about 0.1-2%, preferably from about 0.5-2% of unit (1) on a repeating unit basis.
  • the aminoalkylsilicones comprise amodimethicones.
  • Amodimethicones are polydimethylsiloxane polymers containing aminoalkyl groups.
  • the aminoalkyl groups may be present either pendant or at one or more ends of the polydimethylsiloxane chain.
  • aminoalkylsilicones in which aminoalkyl moiety R is selected from (CH2)3NH2, (CH2)3NHCH2CH2NH2, (CH2)3N(CH 2 CH 2 OH)2, (CH 2 )3NH 3 +X-, and (CH2)3N(CH3)2(Ci8H37)+X", and especially from (CH2)3 H2 and (CH2)3NHCH2CH2NH2.
  • aminoalkyl silicones having an average molecular weight of about 5,000 and above, preferably from about 5000 to about 100,000, more preferably from about 5000 to about 30,000.
  • Aminoalkylsilicone compounds suitable for use herein are well known. Methods of preparing aminoalkylsilicones are given in, for example, US- A-2,930,809.
  • amodimethicones examples include OSI's Magnasof fluid. These polymers comprise aminoalkyl groups affixed to a predominantly polydimethylsiloxane structure. The typical structure of Magnasoft' s aminoalkyl group-containing units is
  • the aminoalkylsilicone is generally present in a level of from about 0.01 % to about 25 % , preferably from about 0.1 % to about 5 % , more preferably from about 0.5% to about 1.5% by weight.
  • compositions of the invention preferably also include a lipophilic compound.
  • lipophilic compounds suitable for use herein are oil-like materials which are soluble or solubilisable in the aminoalkylsilicone, preferably at a level of at least about 1%, more preferably at least about 5% by weight at 25 °C.
  • Preferred lipophilic compounds are selected from flavorants, perfumes, physiological cooling agents and antimicrobial compounds.
  • the aminoalkylsilicone acts to enhance the substantivity of the lipophilic compound to a surface treated therewith, thereby providing enhanced and/or sustained flavor, perfume or coolant impact and/or antimicrobial efficacy.
  • Lipophilic flavorants suitable for use herein comprise one or more flavor components selected from wintergreen oil, oregano oil, bay leaf oil, peppermint oil, spearmint oil, clove oil, sage oil, sassafras oil, lemon oil, orange oil, anise oil, benzaldehyde, bitter almond oil, camphor, cedar leaf oil, marjoram oil, citronella oil, lavendar oil, mustard oil, pine oil, pine needle oil, rosemary oil, thyme oil, cinnamon leaf oil, and mixtures thereof.
  • Lipophilic perfumes suitable for use herein comprise one or more known perfume components inclusive of natural products such as essential oils, absolutes, resins, etc., and synthetic perfume components such as hydrocarbons, alcohols, aldehydes, ketones, ethers, acids, esters, acetals, ketals, nitriles etc., including saturated and unsaturated compounds, aliphatic, carboxylic and heterocyclic compounds.
  • perfume materials suitable for use herein include geranyl acetate, linalyl acetate, citronellyl acetate, dihydromyrcenyl acetate, te ⁇ inyl acetate, tricyclodecenyl acetate, tricyclodecenyl propionate, 2-phenylethyl acetate, benzyl acetate, benzyl salicylate, benzyl benzoate, styrallyl acetate, amyl salicylate, methyl dihydrojasmonate, phenoxy ethyl isobutyrate, neryl acetate, trichloromethyl-phenylcarbinyl acetate, p-tertiary butyl- cyclohexyl acetate, isononyl acetate, cedryl acetate, vetiveryl acetate, benzyl alcohol, 2-phenylethanol, linalool, tetrahydr
  • Lipophilic antimicrobial compounds suitable for use herein include thymol, menthol, triclosan, 4-hexylresorcinol, phenol, eucalyptol, benzoic acid, benzoyl peroxide, butyl paraben, methyl paraben, propyl paraben, salicylamides, and mixtures thereof.
  • Physiological cooling agent suitable for use herein include carboxamides, menthane esters and menthane ethers, and mixtures thereof.
  • Suitable menthane ethers for use herein are selected from those with the formula:
  • R5 is an optionally hydroxy substituted aliphatic radical containing up to 25 carbon atoms, preferably up to 5 carbon atoms, and where X is hydrogen or hydroxy, such as those commercially available under the trade name Takasago, from Takasago International Co ⁇ oration.
  • a particularly preferred cooling agent for use in the compositions of the present invention is Takasago 10 [3-1-menthoxy propan-l,2-diol (MPD)].
  • MPD is a monoglycerin derivative of 1-menthol and has excellent cooling activity.
  • the level of lipophilic compound in the compositions of the invention is generally in the range from about 0.01 % to about 10%, preferably from about 0.05% to about 5%, more preferably from about 0.1 % to about 3% by weight.
  • compositions of the invention optionally include one or more surfactants, these being especially preferred in lipophilic compositions of the invention for the purpose of solubilization of the lipophile and for providing improved efficacy.
  • surfactants include non-soap anionic, nonionic, cationic, zwitter ionic and amphoteric organic synthetic detergents. Many of these suitable agents are disclosed by Gieske et al. in US-A-4,051,234, September 27, 1977.
  • surfactants suitable for use herein include C6 ⁇ C ⁇ g alkyl sulfates and alkyl ether sulfates ethoxylated with from about 0.5 to about 20 moles of ethylene oxide per mole; anionic sulfonates inclusive of C5- C20 linear alkylbenzene sulfonates, alkyl ester sulfonates, C6-C22 primary or secondary alkane sulfonates, C6-C24 olefin sulfonates, sulfonated polycarboxylic acids, alkyl glycerol sulfonates, fatty acyl glycerol sulfonates, and mixtures thereof; anionic carboxylates inclusive of primary and secondary C5 to C ⁇ % alkyl carboxylate, ethoxy carboxylate and polyethoxy polycarboxylate surfactants having an average degree of ethoxy lation of from about 0 to about 10; C5-C17
  • alkylpolysaccharides as disclosed in US-A-4,565,647; amine oxides such as dimethyl cocamine oxide, dimethyl lauryl amine oxide and cocoalkyldimethyl amine oxide (Aromox); polysorbates such as Tween 40 and Tween 80 (Hercules); sorbitan stearates, sorbitan monooleate, etc; cationic surfactants such as cetyl pyridiniura chloride, cetyl trimethyl ammonium bromide, di-isobutyl phenoxy ethoxy ethyl-dimethyl benzyl ammonium chloride and coconut alkyl trimethyl ammonium nitrate.
  • amine oxides such as dimethyl cocamine oxide, dimethyl lauryl amine oxide and cocoalkyldimethyl amine oxide (Aromox)
  • polysorbates such as Tween 40 and Tween 80 (Hercules); sorbitan stearates, sorb
  • nonionic surfactant highly preferred herein from the view point of lipophile solubilization are the nonionic surfactants.
  • One class of nonionic surfactant suitable for use herein are those having the general formula:
  • R ⁇ is an alk(en)yl or alk(en)yl phenyl group having 8 to 22, preferably 10 to 20 carbon atoms ion the alk(en)yl moiety and m and n represent weight-averages in the range 0-80 and 2-80 respectively.
  • Shorter chain length alkyl groups are generally to be avoided for efficacy reasons and because unreacted fatty alcohol in such surfactants is a source of malodour and occasionally of skin irritation. It will be understood that surfactants of this type are usually mixtures of varying degrees of ethoxylation / propoxylation, accordingly m and n represent the respective weight-averages of the number of propoxylate and ethoxylate groups.
  • Nonionic surfactants of the above general type include mixed alkoxylates in which m and n are both in the range from about 2 to about 80, with m preferably being in the range from about 2 to about 20, more preferably from about 3 to about 10 and with n preferably being in the range from about 2 to about 60, more preferably from about 5 to about 50.
  • One such material is PPG-5-ceteth-20 (available from Croda Inc as Procetyl AWS), where m and n have the values 5 and 20 respectively.
  • Other suitable nonionic surfactants include poly ethoxy lated surfactants, e.g.
  • ethoxylated alkylphenol ethers particularly octyl- and nonylphenol ethers containing 8-16 EO; ethoxylated aliphatic C8-C20 alcohols, which may be linear or branched and contain 8-16, preferably 9-15 EO; and ethoxylated hydrogenated castor oils.
  • the ratio of surfactant to the perfume, coolant or other oily material will be in the range of from about 50:1 to about 1:10, preferably from about 20:1 to about 1:2, more preferably from about 10:1 to about 1:1.
  • Bleaching compositions of the invention additionally include one or more bleaching agents optionally together with organic peroxyacid precursors, effervescence generators, chelating agents, etc
  • the bleaching agent takes the form of an inorganic persalt and can be selected from any of the well-known bleaching agents known for use in household bleaches, detergents, denture cleansers and the like such as the alkali metal and ammonium persulfates, perborates inclusive of mono-and tetrahyd rates, percarbonates (optionally coated as described in GB-A- 1,466,799) and pe ⁇ hosphates and the alkali metal and alkaline earth metal peroxides.
  • suitable bleaching agents include potassium, ammonium, sodium and lithium persulfates and perborate mono- and tetrahydrates, sodium pyrophosphate peroxyhydrate and magnesium, calcium, strontium and zinc peroxides.
  • the amount of bleaching agent in the bleaching compositions of the invention is generally from about 5 to about 70% preferably from about 10% to about 50%.
  • the bleaching compositions can also inco ⁇ orate an effervescence generator which in preferred embodiments takes the form of a solid base material which in the presence of water releases carbon dioxide or oxygen with effervescence.
  • the effervescence generator can be selected from generators which are effective under acid, neutral or alkaline pH conditions, but preferably it consists of a combination of a generator which is effective or most effective under acid or neutral pH conditions and a generator which is effective or most effective under alkaline pH conditions.
  • Effervescence generators which are effective under acid or neutral pH conditions include a combination of at least one alkali metal carbonate or bicarbonate, such as sodium bicarbonate, sodium carbonate, sodium sesquicarbonate, potassium carbonate, potassium bicarbonate, or mixtures thereof, in admixture with at least one non-toxic, physiologically-acceptable organic acid, such as tartar ic, fumaric, citric, malic, maleic, glu conic, succinic, salicylic, adipic or sulphamic acid, sodium fumarate, sodium or potassium acid phosphates, betaine hydrochloride or mixtures thereof. Of these, malic acid is preferred.
  • Effervescence generators which are effective under alkaline pH conditions include persalts such as alkali and alkaline earth metal peroxoborates as well as perborates, persulphates, percarbonates, pe ⁇ hosphates and mixtures thereof as previously described, for example, a mixture of an alkali metal perborate (anhydrous, mono- or tetrahydrate) with a monopersulphate such as Caroat R marketed by E I du Point de Nemours Co. and which is a 2:1:1 mixture of monopersulphate, potassium sulphate and potassium bisulphate and which has an active oxygen content of about 4.5%.
  • persalts such as alkali and alkaline earth metal peroxoborates as well as perborates, persulphates, percarbonates, pe ⁇ hosphates and mixtures thereof as previously described, for example, a mixture of an alkali metal perborate (anhydrous, mono- or tetrahydrate) with a monopersulphate such as Caroat R marketed by
  • the solid base material inco ⁇ orates a (bi)carbonate/acid effervescent couple optionally in combination with a perborate/persulphate oxygen effervescence generator.
  • the combination of generators is valuable for achieving optimum dissolution characteristics and pH conditions for achieving optimum cleaning and antimicrobial activity.
  • the (bi)carbonate components generally comprise from about 5% to about 65%, preferably from about 25% to 55% of the total composition; the acid components generally comprise from about 5% to about 50%, preferably from about 10% to about 30% of the total composition.
  • the bleaching compositions of the invention can be supplemented by other known components of such formulations.
  • An especially preferred additional component is an organic peroxyacid precursor, which in general terms can be defined as a compound having a titre of at least 1.5ml of 0.1 N sodium thiosulfate in the following peracid formation test.
  • test solution is prepared by dissolving the following materials in 1000 mis distilled water:
  • the mixture obtained by addition of the activator is vigorously stirred and maintained at 60°C. After 5 minutes from addition, a 100 ml portion of the solution is withdrawn and immediately pipetted onto a mixture of 250 g cracked ice and 15 ml glacial acetic acid. Potassium iodide (0.4 g) is then added and the liberated iodine is immediately titrated with 0.1 N sodium thiosulphate with starch as indicator until the first disappearance of the blue colour. The amount of sodium thiosulphate solution used in ml is the titre of the bleach activator.
  • the organic peracid precursors are typically compounds containing one or more acyl groups, which are susceptible to perhydrolysis.
  • the preferred activators are those of the N-acyl or O-acyl compound type containing a acyl radical R-CO wherein R is a hydrocarbon or substituted hydrocarbon group having preferably from about 1 to about 20 carbon atoms.
  • suitable peracid precursors include:
  • N,N - diacetylaniline and N-acetylphthalimide a) N,N - diacetylaniline and N-acetylphthalimide; b) N-acylhydantoins, such as
  • Examples of compounds of this type include phenyl acetate, sodium acetoxy benzene sulphonate, trichloroethylacetate, sorbitol hexaacetate, fructose pentaacetate, p- nitrobenzaldehyde diacetate, isopropeneyl acetate, acetyl aceto hydroxamic acid, and acetyl salicylic acid.
  • esters of a phenol or substituted phenol with an alpha-chlorinated lower aliphatic carboxylic acid such as chloroacetylphenol and chloroacetylsalicylic acid, as disclosed in US-A-3,130,165.
  • Preferred compounds of this type are those wherein: a) Ac is R3-CO and R3 is a linear or branched alkyl group containing from 6 to 20, preferably 6 to 12, more preferably 7 to 9 carbon atoms and wherein the longest linear alkyl chain extending from and including the carbonyl carbon contains from 5 to 18, preferably 5 to 10 carbon atoms, R3 optionally being substituted (preferably alpha to the carbonyl moiety) by Cl, Br, OCH3 or OC2H5.
  • this class of material examples include sodium 3,5,5-trimethylhexanoyloxybenzene sulfonate, sodium 3,5,5-trimethylhexanoyloxybenzoate, sodium 2- ethylhexanoyl oxybenzenesulfonate, sodium nonanoyl oxybenzene sulfonate and sodium octanoyl oxybenezenesulfonate, the acyloxy group in each instance preferably being p-substituted;
  • R3(AO) m XA wherein R3 is a linear or branched alkyl or alkylaryl group containing from 6 to 20, preferably from 6 to 15 carbon atoms in the alkyl moiety, R5 being optionally substituted by Cl, Br, OCH3, or OC2H5, AO is oxyethylene or oxypropylene, m is from 0 to 100, X is O, NR4 or CO-NR4, and A is CO, CO-CO, R6-CO, CO-R ⁇ -CO, or CO-NR4-R6-CO wherein R4 is C1-C4 alkyl and R$ is alkylene, alkenylene, arylene or alkarylene containing from 1 to 8 carbon atoms in the alkylene or alkenylene moiety.
  • m is preferably from 0 to 10
  • R3 is preferably Cfr C12, more preferably alkyl when m is zero and C9- C15 when m is non-zero.
  • the leaving group L is as
  • Optionally substituted anhydrides of benzoic or phthalic acid for example, benzoic anhydride, m-chlorobenzoic anhydride and phthalic anhydride.
  • N-acylated precursor compounds of the lactam class as disclosed generally in GB-A-855735 especially caprolactams and valerolactams such as benzoyl valerolactam, benzoyl caprolactam and their substituted benzoyl analogs such as the chloro, amino, alkyl, aryl and alkoxy derivatives.
  • the level of peroxyacid bleach precursor by weight of the total composition is preferably from about 0.1 % to about 10%, more preferably from about 0.5% to about 5% and is generally added in the form of a bleach precursor agglomerate.
  • the bleach precursor agglomerates preferred for use herein generally comprise a binder or agglomerating agent in a level of from about 5% to about 40%, more especially from about 10% to about 30% by weight thereof.
  • Suitable agglomerating agents include polyvinylpyrrolidone, poly (oxyethylene) of molecular weight 20,000 to 500,000, polyethyleneglycols of molecular weight of from about 1000 to about 50,000, Carbowax having a molecular weight of from 4000 to 20,000, nonionic surfactants, fatty acids, sodium carboxy methyl cellulose, gelatin, fatty alcohols, phosphates and polyphosphates, clays, aluminosilicates and polymeric polycarboxylates.
  • polyethyleneglycols are highly preferred, especially those having molecular weight of from about 1 ,000 to about 30,000, preferably 2000 to about 10,000.
  • bleach precursor agglomerates which comprise from about 10% to about 75%, preferably from about 20% to about 60% by weight thereof of peroxyacid bleach precursor, from about 5 % to about 60% preferably from about 5% to about 50%, more preferably from about 10% to about 40% of a (bi) carbonate/acid effervescent couple, from about 0% to about 20% of a peroxoboroate, and from about 5% to about 40%, preferably from about 10% to about 30% of an agglomerating agent.
  • the final bleach precursor granules desirably have an average particle size of from about 500 to about 1500, preferably from about 500 to about 1 ,000 urn, this being valuable from the viewpoint of optimum dissolution performance and aesthetics.
  • the level of bleach precursor agglomerates is preferably from about 1 % to about 20%, more preferably from about 5% to about 15% by weight of composition.
  • compositions of the invention can be in paste, tablet, granular or powder form.
  • Compositions in tablet form can be single or multiple layered tablets.
  • Bleaching compositions of the invention can be supplemented by other usual components of such formulations, especially surfactants as generally described above, chelating agents, enzymes, dyes tuffs, sweeteners, tablet binders and fillers, foam depressants such as dimethylpolysiloxanes, foam stabilizers such as the fatty acid sugar esters, preservatives, lubricants such as talc, magnesium stearate, finely divided amo ⁇ hous pyrogenic silicas, etc.
  • surfactants as generally described above, chelating agents, enzymes, dyes tuffs, sweeteners, tablet binders and fillers, foam depressants such as dimethylpolysiloxanes, foam stabilizers such as the fatty acid sugar esters, preservatives, lubricants such as talc, magnesium stearate, finely divided amo ⁇ hous pyrogenic silicas, etc.
  • Tablet binders and fillers suitable for use herein include polyvinylpyrrolidone, poly (oxyethylene) of molecular weight 20,000 to 500,000, polyethyleneglycols of molecular weight of from about 1000 to about 50,000, Carbowax having a molecular weight of from 4000 to 20,000, nonionic surfactants, fatty acids, sodium carboxymethyl cellulose, gelatin, fatty alcohols, clays, polymeric polycarboxylates, sodium carbonate, calcium carbonate, calcium hydroxide, magnesium oxide, magnesium hydroxide carbonate, sodium sulfate, proteins, cellulose ethers, cellulose esters, poly vinyl alcohol, alginic acid esters, vegetable fatty materials of a pseudocolloidal character.
  • polyethyleneglycols are highly preferred, especially those having molecular weight of from about 1 ,000 to about 30,000, preferably from about 12,000 to about 30,000.
  • Chelating agents beneficially aid cleaning and bleach stability by keeping metal ions, such as calcium, magnesium, and heavy metal cations in solution.
  • suitable chelating agents include sodium tripolyphosphate, sodium acid pyrophosphate, tetrasodium pyrophosphate, aminopolycarboxylates such as nitrilotriacetic acid and ethylenediamine tetracetic acid and salts thereof, ethylenediamine-N,N'-disuccinic acid (EDDS) and salts thereof, and polyphosphonates and aminopolyphosphonates such as hydroxyethanediphosphonic acid, ethylenediamine tetramethylenephosphonic acid, diethylenetriaminepentamethylenephosphonic acid and salts thereof.
  • EDDS ethylenediamine-N,N'-disuccinic acid
  • the chelating agent selected is not critical except that it must be compatible with the other ingredients of the denture cleanser when in the dry state and in aqueous solution.
  • the chelating agent comprises between 0.1 and 60 percent by weight of the composition and preferably between 0.5 and 30 percent.
  • Phosphonic acid chelating agents preferably comprise from about 0.1 to about 1 percent, preferably from about 0.1 % to about 0.5% by weight of composition.
  • Enzymes suitable for use herein are exemplified by proteases, alkalases, amylases, fungal and bacterial Upases, dextranases, mutanases, glucanases, esterases, cellulases, pectinases, lactases and peroxidases, etc. Suitable enzymes are discussed in US- A-3, 519,570 and US-A- 3,533,139.
  • the following are representative denture cleansing tablets according to the invention.
  • the percentages are by weight of the total tablet.
  • the tablets are made by compressing a mixture of the granulated components in a punch and dye tabletting press at a pressure of about 10 ⁇ kPa.
  • the overall tablet weight is 3 g; diameter 25 mm.
  • the denture cleansing tablets of Examples I to V display improved antiplaque, cleansing and anti-bacterial activity together with excellent cohesion and other physical and in-use performance characteristics.
  • perfume, flavour, coolant and antimicrobial compositions are representative perfume, flavour, coolant and antimicrobial compositions according to the invention.
  • the percentages are by weight of total composition.
  • Perfume is a complex mixture of ingredients used primarily for olfactory pu ⁇ oses.
  • the perfume, flavor, coolant and/or antimicrobial compositions of Examples VI to IX display improved surface-substantivity, impact and/or efficacy.

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Abstract

Composition contenant un agent de sapidité, un parfum, un agent de refroidissement ou un agent antimicrobien, renfermant un aminoalkylsilicone dont la teneur en aminoalkylsiloxane est comprise entre environ 0, 1 % et 2 % sur la base d'une unité répétitive. Ladite composition réside plus longtemps sur les surfaces, a un effet plus soutenu et/ou présente une efficacité antimicrobienne améliorée.
EP95943372A 1994-12-22 1995-12-05 Compositions a base de silicone Withdrawn EP0794763A4 (fr)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
GBGB9425930.6A GB9425930D0 (en) 1994-12-22 1994-12-22 Silicone compositions
GB9425930 1994-12-22
PCT/US1995/015766 WO1996019194A1 (fr) 1994-12-22 1995-12-05 Compositions a base de silicone

Publications (2)

Publication Number Publication Date
EP0794763A1 EP0794763A1 (fr) 1997-09-17
EP0794763A4 true EP0794763A4 (fr) 1999-06-09

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EP95943372A Withdrawn EP0794763A4 (fr) 1994-12-22 1995-12-05 Compositions a base de silicone

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EP (1) EP0794763A4 (fr)
JP (1) JP3836876B2 (fr)
CN (1) CN1101227C (fr)
AU (1) AU4465296A (fr)
BR (1) BR9510277A (fr)
CA (1) CA2208371C (fr)
CZ (1) CZ188497A3 (fr)
GB (1) GB9425930D0 (fr)
HU (1) HUT77478A (fr)
MX (1) MX9704724A (fr)
NZ (1) NZ298935A (fr)
PL (1) PL321858A1 (fr)
SA (1) SA96160591B1 (fr)
SK (1) SK83397A3 (fr)
TR (1) TR199501653A2 (fr)
WO (1) WO1996019194A1 (fr)

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US6294154B1 (en) 1994-12-22 2001-09-25 Procter And Gamble Company Oral compositions containing dimethicone copolyols
DE19650102A1 (de) * 1996-12-03 1998-06-04 Basf Ag Verwendung von Bis(dicarbonsäure)diaminoalkylen-Derivaten als biologisch abbaubare Komplexbildner für Erdalkali- und Schwermetallionen
US6040288A (en) * 1997-02-21 2000-03-21 Rhodia Inc. Fabric color protection compositions and methods
AU2284699A (en) * 1998-02-11 1999-08-30 Rhodia Chimie Dirt removing detergent compositions
AU2284799A (en) * 1998-02-11 1999-08-30 Rhodia Chimie Detergent compositions containing an amine silicone and a polymer inhibiting colour transfer
ATE533515T1 (de) 1999-01-27 2011-12-15 Coda Therapeutics Inc Formulierungen enthaltend antisense nukleotide spezifisch für connexine
GB0316927D0 (en) * 2003-07-18 2003-08-27 Stephens Michael J A composition for use in the treatment of a surface
JP5838017B2 (ja) 2003-12-03 2015-12-24 コーダ セラピューティクス， インコーポレイテッド コネキシンに対して標的化されたアンチセンス化合物およびその使用方法
JP4637494B2 (ja) * 2004-03-25 2011-02-23 高砂香料工業株式会社 義歯洗浄剤
US20060003913A1 (en) * 2004-06-30 2006-01-05 The Procter & Gamble Company Perfumed liquid laundry detergent compositions with functionalized silicone fabric care agents
KR20080031154A (ko) 2005-02-03 2008-04-08 코다 테라퓨틱스 (엔지) 리미티드 항-코넥신 화합물 및 그의 용도
GB0526292D0 (en) * 2005-12-23 2006-02-01 Endurocide Ltd A composition for use in the treatment of a surface
EP2040550A2 (fr) * 2006-07-14 2009-04-01 Ciba Holding Inc. Derives de polysiloxane antimicrobiens
WO2008073479A2 (fr) 2006-12-11 2008-06-19 Coda Therapeutics, Inc. Compositions et traitements de cicatrisation de plaies aggravées
AU2008343841A1 (en) 2007-12-21 2009-07-09 Coda Therapeutics, Inc. Use of inhibitors of connexin43 for treatment of fibrotic conditions
CN114010788A (zh) 2014-08-22 2022-02-08 奥克兰联合服务有限公司 通道调节剂
GB2545007A (en) * 2015-12-03 2017-06-07 Cosmetic Warriors Ltd Composition
JP6953707B2 (ja) * 2016-11-30 2021-10-27 ライオン株式会社 液体義歯洗浄剤組成物

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WO1979000454A1 (fr) * 1977-12-29 1979-07-26 Minnesota Mining & Mfg Composition et procede pour empecher la formation de la plaque dentaire
EP0398177A2 (fr) * 1989-05-17 1990-11-22 Kao Corporation Composition détergente
EP0528457A1 (fr) * 1991-08-07 1993-02-24 Unilever N.V. Compositions orales contenant une aminosilicone et composé lipophile

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US2930809A (en) * 1956-10-12 1960-03-29 Union Carbide Corp Aminoalkylsilicon compounds and process for producing same
US3624120A (en) * 1969-12-22 1971-11-30 Procter & Gamble Quaternary ammonium salts of cyclic siloxane polymers
US4136163A (en) * 1971-02-04 1979-01-23 Wilkinson Sword Limited P-menthane carboxamides having a physiological cooling effect
JPH06509816A (ja) * 1992-06-16 1994-11-02 フイルメニツヒ ソシエテ アノニム 香料添加された組成物

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WO1979000454A1 (fr) * 1977-12-29 1979-07-26 Minnesota Mining & Mfg Composition et procede pour empecher la formation de la plaque dentaire
EP0398177A2 (fr) * 1989-05-17 1990-11-22 Kao Corporation Composition détergente
EP0528457A1 (fr) * 1991-08-07 1993-02-24 Unilever N.V. Compositions orales contenant une aminosilicone et composé lipophile

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Also Published As

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JP3836876B2 (ja) 2006-10-25
CA2208371C (fr) 2002-02-26
CA2208371A1 (fr) 1996-06-27
SA96160591B1 (ar) 2005-04-17
MX9704724A (es) 1997-10-31
NZ298935A (en) 1999-10-28
SK83397A3 (en) 1998-01-14
CN1101227C (zh) 2003-02-12
TR199501653A2 (tr) 1996-07-21
WO1996019194A1 (fr) 1996-06-27
BR9510277A (pt) 1998-01-06
CZ188497A3 (en) 1997-11-12
GB9425930D0 (en) 1995-02-22
CN1170352A (zh) 1998-01-14
EP0794763A1 (fr) 1997-09-17
AU4465296A (en) 1996-07-10
HUT77478A (hu) 1998-05-28
JPH10511093A (ja) 1998-10-27
PL321858A1 (en) 1997-12-22

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