US2783182A - Non-staining chlorophyll preparations - Google Patents

Non-staining chlorophyll preparations Download PDF

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Publication number
US2783182A
US2783182A US338607A US33860753A US2783182A US 2783182 A US2783182 A US 2783182A US 338607 A US338607 A US 338607A US 33860753 A US33860753 A US 33860753A US 2783182 A US2783182 A US 2783182A
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United States
Prior art keywords
chlorophyll
weight
polyvinylpyrrolidone
soluble
water
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Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Expired - Lifetime
Application number
US338607A
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English (en)
Inventor
Jr Manno Fredrick Nelson
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.)
Colgate Palmolive Co
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Colgate Palmolive Co
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Filing date
Publication date
Priority to NL87045D priority Critical patent/NL87045C/xx
Priority to BE526730D priority patent/BE526730A/xx
Priority to NLAANVRAGE8100494,A priority patent/NL185343B/xx
Application filed by Colgate Palmolive Co filed Critical Colgate Palmolive Co
Priority to US338607A priority patent/US2783182A/en
Priority to GB4862/54A priority patent/GB739936A/en
Priority to DEC8920A priority patent/DE966246C/de
Priority to CH327917D priority patent/CH327917A/de
Application granted granted Critical
Publication of US2783182A publication Critical patent/US2783182A/en
Anticipated expiration legal-status Critical
Expired - Lifetime 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
    • A61Q15/00—Anti-perspirants or body deodorants
    • 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
    • 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
    • A61K8/49—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
    • A61K8/494—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with more than one nitrogen as the only hetero atom
    • 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
    • A61K8/81—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds
    • A61K8/817—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a single or double bond to nitrogen or by a heterocyclic ring containing nitrogen; Compositions or derivatives of such polymers, e.g. vinylimidazol, vinylcaprolactame, allylamines (Polyquaternium 6)
    • A61K8/8176—Homopolymers of N-vinyl-pyrrolidones. Compositions of derivatives of such polymers
    • 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
    • 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
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q9/00—Preparations for removing hair or for aiding hair removal
    • A61Q9/02—Shaving preparations
    • 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
    • A61K2800/26—Optical properties
    • 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
    • A61K2800/40—Chemical, physico-chemical or functional or structural properties of particular ingredients
    • A61K2800/52—Stabilizers
    • 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
    • A61K2800/40—Chemical, physico-chemical or functional or structural properties of particular ingredients
    • A61K2800/58—Metal complex; Coordination compounds

Definitions

  • the present invention relates to novel preparations comprising in combination a chlorophyll compound and polyvinylpyrrolidone, as hereinafter described and claimed.
  • Chlorophyll and various derivatives thereof, such as chlorophyllins have been employed in pharmaceutical, cosmetic and detergent compositions and various other fields of application for many years. Such materials have been proposed for many uses including Wound treatments, breath and body deodorization, as coloring agents, etc.
  • chlorophyll compounds and the like tend to deposit or produce an undesirable stain upon suitable absorbent materials.
  • the degree of staining power is dependent to some extent upon the amount of chlorophyll compound present and the type or nature of the composition, but the undesirable effects range from a pale green to blackish discoloration or stain.
  • the nature of the absorbent surface is a vital factor also, and materials comprising cellulose, animal and synthetic fibers, etc, appear to be particularly susceptible to deposition of the stain.
  • use of a dental cream containing Water-soluble chlorophyllin in the ordinary or conventional manner with a tooth brush results in a greenish staining or discoloration of the tooth brush bristles which cannot be removed by ordinaryrinsing or washing of the brush.
  • a preferred embodiment of the present invention relates to a dentifrice comprising at least about 20% of polishing material, up to 5% by weight of tates Patent 0 an organic detergent, about .001 to 5% by Weight of a water-soluble chlorophyll compound or chlorophyllin normally tending to stain or discolor absorbent materials and up to 5% by weight and having an average molecular weight of 10,000 to 300,000 of a water-soluble polyvinylpyrrolidone as an anti-staining agent.
  • Various other preferred embodiments will be apparent in the following description.
  • Polyvinylpyrrolidone has received some degree of recognition in blood plasma therapy. It is usually prepared by polymerizing N-vinylpyrrolidone (monomer) molecules. in known manner to any desired molecular weight or degree of polymerization. 7 Any suitable water-soluble polyvinylpyrrolidone as described, may be used in the present invention. In general, such materials are non-toxic, high molecular Weight polymers of 1 or N-vinyl 2-pyrrolidone, which are soluble in water colloidally.
  • the specific or exact degree of polymerization is not believed critical provided'the desired Water-solubility and non-toxic effects are maintained since the productsusually comprise a mixture of specific polymers each containing a diiferent number of monomer units, depending upon the, manner and degree of polymerization, fractionation, if any, etc.
  • the stain inhibiting eificacy of the product is an observable phenomenon and readily determinable by simple procedures in view of the present invention.
  • suitable polymers having an average molecular weight within the range of about 5,000 to about 500,000 should be employed in the present invention. It will generally be desirable to use products having an average molecular weight of about 10,000 to 300,000, and usually about 10,000 to 150,000. Excellent. desired effects have been obtained withpolymers of average molecular Weight within the range of about 20,000 to about 100,000, with optimum results usually at a range of about 25,000 to about 60,000. Further specific suitable examples are polymers having an, average molecular weight of about 20,000, 27,000, 30,000, 40,000, 100,000, 150,000, and 200,000, etc.
  • the invention is applicable to any chlorophyll composition containing the same which normally exhibits a tendency to stain a suitable absorbent (or adsorbent) surface.
  • chlorophyll which stain the absorbent surface upon mere contact and to compositions such as powders, etc., which normally exhibit some staining tendency after contact with water or other suitable solvent or liquid medium.
  • chlorophyll is used herein generically, as inclusive of the natural chlorophyll material per se, the various oilsoluble andwater-soluble chlorophyll materials and derivatives thereof, etc. Included among the fat-soluble or oil-soluble chlorophylls are the green pigmnts chlorophyll a, chlorophyll b and mixtures thereof which are usually present in nature and products of commercial manufacture.
  • chlorophyll molecules are pyrolle pigments containing phytyl and methyl ester groups and magnesium bound in a complex linkage in a prophyrin system.
  • Variou derivatives thereof may be formed in known manner. For example, the displacement of the magnesium by hydrogen or other metals such as copper, iron or nickel results in compounds known as pheophytins.
  • Other derivatives includes pheophorbides and chlorophyllides such as are obtained by replacement of the phytyl group by an ethyl radical.
  • chlorophyllin or water-soluble its admixture with polyvinylpyrrolidone are preferred to use chlorophyllin or water-soluble its admixture with polyvinylpyrrolidone.
  • These watersoluble derivatives may be synthesized from the oil-soluble. forms in know manner, such as by saponification 3 with alkali to form a water-soluble salt.
  • Suitable examples are sodium copper chlorophyllin, potassium copper chlorophyllin, sodium magnesium chlorophyllin, sodium nickel chlorophyllin, sodium iron chlorophyllin, sodium potassium copper chlorophyllin and potassium magnesium chlorophyllin.
  • the polyvinylpyrrolidone and chorophyll exert their beneficial functions in widely variable proportions depending upon the specific nature of the polymer, the chlorophyll compound and the type of composition.
  • the vinylpyrrolidone polymer may be admixed with the chlorophyll in any suit-able manner and type of composition which permits the polymer to exert the desired anti-staining effects.
  • the amount of vinylpyrrolidone polymer required to inhibit or prevent discoloration is readily determinable and the effects are, to some extent, proportional to the amount of polymer added compared to a constant amount of chlorophyll up to an optimum efiect.
  • novel compositions comprising chlorophyll and polyvinylpyrrolidone may be prepared and marketed in any desired form including liquid, semi-solid and solid form.
  • preparations are powders, solutions, suspensions, emulsions, salves, ointments, creams, pastes, lotions, .tablets, and the like.
  • preparations may contain various adjuvant materials in suitable amounts provided the same do not substantially adversely affect the improved results produced by the mixture of chlorophyll and polyvinylpyrrolidone.
  • Such optional added ingredients include suitable perfumes and flavoring oils, sweetening agents, preservatives, emulsifying and solubilizing agents, hydrophobic and hydrophilic ingredients or vehicles, and other materials in use in cosmetic (including pharmaceutical) preparations.
  • suitable materials are glycerine, sodium benzoate, castor oil, lanolin, acetone, alcohol, fatty acid monoand di-ester of polyhydric alcohols, sodium chloride, etc.
  • the compositions may comprise chiefly the two essential ingredients.
  • the polyvinylpyrrolidone in the form of powder, solutions or suspensions may be admixed in any suitable proportions with the solid, liquid or semi-solid concentrates of chlorophyll of varying purity which are produced by commercial manufacture.
  • An illustrative technical or commercial product is sodium The desirable a'a'sansav h copper chlorophyllin or potassium sodium copper chlorophyllin prepared as a granular solid containing various impurities and which may be dissolved in water in amounts up to about 15% by weight depending upon purity.
  • Commercial oil-soluble chlorophyll products are prepared usually in liquid or solution form in amounts up to about 15 concentration also.
  • these novel mixtures of chlorophyll and polyvinylpyrrolidone may be utilized in preparations designed for application in the mouth.
  • Such oral or dentifrice preparations include suitable tooth powders, dental creams, tooth pastes, liquid dentifrices, mouth washes or rinses, tablets, etc.
  • the amounts of these ingredients are widely variable relative to the balance of the oral compositions. The specific amounts will vary, naturally, depending upon the type of composition, e. g., dental cream, liquid or powder, and the specific effects desired.
  • the chlorophyll and polyvinylpyrrolidone will each be a minor amount or proportion by weight of the total composition.
  • the chlorophyll should be present in any suitable amount such as from about .001 up to about 10% by weight whereas the polyvinylpyrrolidone may be utilized in amounts up to about 10% by weight in a suitable non-toxic carrier or vehicle.
  • the polyvinylpyrrolidone and chlorophyll will be preferably up to about 5% by weight of the finished formulation.
  • Each of these essential ingredients may be incorporated in the composition in any suitable manner, such as in the form of powders, solutions, suspensions, etc.
  • any suitable practically water-insoluble polishing agent may be admixed with these novel compounds in the preparation of dentifrice compositions of the present invention.
  • Representative materials include, for example, calcium carbonate, dicalcium phosphate (anhydrous or hydrated), tricalcium phosphate, insoluble sodium metaphosphate, aluminum hydroxide, magnesium carbonate, calcium sulfate, bentonite, etc., including suitable mixtures thereof.
  • these polishing agents will comprise a major proportion by weight of the solid ingredients.
  • the polishing agent content is variable, but will generally be up to about by Weight of the total composition. In the case of a dental cream such polishing agents will generally be about 20-75% whereas in tooth powders, the polishing agents will usually be a major proportion, such as about 7095%.
  • the liquids and solids should necessarily be proportioned to form a creamy mass of desired consistency which is extrudible from a collapsible aluminum orlead tube.
  • the liquids in the dental cream will comprise chiefly water, glycerine, sorbitol, propylene glycol, etc., including "suitable mixtures thereof. It is usually advantageous to use a mixture of both water and a hnmectant or hinder such as glycerine, sorbitol, etc.
  • the total liquid content will generally be about 20-75% by weight of the formulation.
  • a suitable surface-active agent such as wetting agents or preferably a water-soluble detergent compound to yield added foaming power and other surface-active properties, such surface active agents being usually characterized by having a long aliphatic chain in the molecule and a water-solubilizing group.
  • an anionic organic detergent in admixture with the essential ingredients.
  • detersive agents include, for example, the water-soluble salts ease-tee of higher fatty acid monoglyceridemonosulfate detergent (e. g., sodium salt of monosulfated monoglycerides of higher fatty acids of coconut oil), higher fatty acid amide of amino carboxylic acid (e.
  • these detersive agents may be used in any suitable amount, such as up to about 20 and usually up to by weight. In the case of non-soap or synthetic detergents they will be employed usually in an amount up to about 5% by weight.
  • adjuvant materials are usually incorporated in suitable amounts, particularly in dental creams. It is preferred to use a gelling agent such as the natural and synthetic gums and gum-like materials, e. g., Irish moss, gum tragacanth, sodium carboxymethylcellulose, starch, etc., usually in an amount up to 10% by weight of the dental cream, and preferably from 0.55%. Furthermore, such materials as soluble saccharin, flavoring oils (e. g., oils of spearmint, peppermint), preservatives, alcohol, etc., may be used as desired in proper amount.
  • a gelling agent such as the natural and synthetic gums and gum-like materials, e. g., Irish moss, gum tragacanth, sodium carboxymethylcellulose, starch, etc.
  • soluble saccharin e. g., flavoring oils (e. g., oils of spearmint, peppermint), preservatives, alcohol, etc., may be used as desired in proper amount.
  • Mouth washes or rinses are also within the scope of the present invention.
  • Such products are usually an effective amount of detergent or antiseptic dissolved or dispersed in a suitably flavored liquid vehicle, preferably aqueous alcoholic vehicle in which may be incorporated suitable amount of polyvinylpyrrolidone and chlorophyllin.
  • the alcohol concentration may vary depending on the mouth eflect desired, such as about 5-70% alcohol, and preferably 540%.
  • Liquid dentifrices are also included, such productsvusually containing a minor amount of detergent, usually dis-solved or dispersed inan aqueous alcoholic vehicle, preferably containing a mucilaginous material and optionally combined with small amounts of polishing agent, glycerine, coloring and flavoring materials.
  • the pH of the final formulations of the present invention is variable and, therefore, the products may have any suitable pH value in solution compatible with the stability of the materials.
  • pH values it has reference to the pH as determined on a liquid product per se, and in the case of a dental cream or power or similar product as determined on a aqueous slurry or mixture of said cream or powder.
  • the pH of the product under the testing conditions indicated be from about 5 up to about 10, and preferably from' about 5.5 to 9, with optimum desired effects at a substantially neutral pH value in solution, e. g., about 6 to 8.
  • Example I A dental cream is prepared in the usual manner according to the following formulation:
  • Percent Polyvinylpyrrolidone (av. m. w. 40,000) 0.5 Sodium copper chlorophyllin 0.1 Dicalcium phosphate dihydrate 48.25 Glycerine 28.2 Detergent; 3.75 Tetrasodium pyrophosphate 1.0
  • the detergent is a sodium salt of monoglyceride monosulfates of higher fatty acids derived from coconut oil.
  • Example II To separate portions of a commercial chlorophyllcontaining dental cream comprising about 45% polishing agent, a minor amount 'of detergent and about 0.1% sodium copper chlorophyllin, there is added said polyvinylpyrolidone in powder form in 0.5%, 1 and 2% concentrations by weight respectively. Each portion of the cream was stirred to homogeneously disperse the polyvinylpyrrolidone therein. These creams were admixed with water to form an aqueous slurry, filtered and cotton swatches were added to the filtrate after which the swatches were dried and washed in a soap solution.
  • Example III One half of an artificial denture containing polyacrylic resin as the base plate is brushed with a wet toothbrush containing a similar chlorophyll-containing dental cream having 0.5% of said polyvinylpyrrolidone. After cleaning with this cream, this portion of the denture exhibits no chlorophyll stain whereas identical treatment with a similar composition free of polyvinylpyrrolidone on the remaining half of the denture results in the deposition of a greenish stain.
  • Example IV A solution of .0l% oil-soluble chlorophyll in mineral oil is prepared to which is added 1% of said polyvinylpyrrolidone.
  • a cotton swatch is dipped in the solution for 10 minutes and removed therefrom, resulting in a light green stain on the cloth.
  • This swatch is then rinsed and washed in a detergent solution for several minutes resulting in substantially complete removal of any stain.
  • a chlorophyll solution which does not contain the vinylpyrrolidone polymer resultsin a deep penetrating green stain on the cotton swatch which is not removed to any significant extent by washing.
  • Example V -Dental cream Sodium coconut monoglyceride monosulfateun n 4.0
  • Polyvinylpyrrolidone (as described) 10.0
  • Detergent 9.0 Irish moss gum 1.25
  • Ethyl alcohol 10.0
  • Soluble saccharin 0.5
  • a chlorophyll-containing composition normally tending to deposit a greenish stain on an absorbent surface comprising chlorophyll in an amount from .001 to 10% by weight in a non-toxic carrier, and having incorporated therein a water-soluble polyvinylpyrrolidone having an average molecular weight from about 5,000 to 500,000 in. an amount up to 10% by weight as an antistaining agent, the ratio of said polyvinylpyrrolidone to said chlorophyll being at least about 1:1 by weight and sufiicient to inhibit the staining of the absorbent surface by the chlorophyll.
  • composition in accordance with claim 1 containing chlorophyllin and water-soluble polyvinylpyrrolidone having an average molecular weight of about 10,000 to 300,000 in an aqueous carrier.
  • a dentifrice composition comprising at least about 20% by weight of polishing material, up to 5% by weight of an organic detergent, about .001 to 5% by weight of chlorophyllin normally tending to deposit a greenish stain on an absorbent surface, and up to 5% by weight of a water-soluble polyvinylpyrrolidone having an average molecular weight of 10,000 to 300,000, the ratio of said polyvinylpyrrolidone to said chlorophyllin being at least about 1:1 by weight and sufficient to inhibit the staining of the absorbent surface by the chlorophyllin.

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  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Birds (AREA)
  • Epidemiology (AREA)
  • Oral & Maxillofacial Surgery (AREA)
  • Inorganic Chemistry (AREA)
  • Chemical & Material Sciences (AREA)
  • Dermatology (AREA)
  • Cosmetics (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
US338607A 1953-02-24 1953-02-24 Non-staining chlorophyll preparations Expired - Lifetime US2783182A (en)

Priority Applications (7)

Application Number Priority Date Filing Date Title
NL87045D NL87045C (en]) 1953-02-24
BE526730D BE526730A (en]) 1953-02-24
NLAANVRAGE8100494,A NL185343B (nl) 1953-02-24 Gevormde farmaceutische preparaten met antilipemische ontstekingswerende en immuniteitregelende werking en daarvoor geschikte sulfonaatverbindingen en een bereidingswijze.
US338607A US2783182A (en) 1953-02-24 1953-02-24 Non-staining chlorophyll preparations
GB4862/54A GB739936A (en) 1953-02-24 1954-02-18 Chlorophyll preparations
DEC8920A DE966246C (de) 1953-02-24 1954-02-20 Chlorophyllhaltige kosmetische Zubereitungen
CH327917D CH327917A (de) 1953-02-24 1954-02-23 Chlorophyllhaltiges Präparat

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US338607A US2783182A (en) 1953-02-24 1953-02-24 Non-staining chlorophyll preparations

Publications (1)

Publication Number Publication Date
US2783182A true US2783182A (en) 1957-02-26

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ID=23325411

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US338607A Expired - Lifetime US2783182A (en) 1953-02-24 1953-02-24 Non-staining chlorophyll preparations

Country Status (6)

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US (1) US2783182A (en])
BE (1) BE526730A (en])
CH (1) CH327917A (en])
DE (1) DE966246C (en])
GB (1) GB739936A (en])
NL (2) NL87045C (en])

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2471780A1 (fr) * 1979-12-19 1981-06-26 Colgate Palmolive Co Composition de pate dentifrice
EP0051752A3 (en) * 1980-11-12 1983-02-09 Weilin Liau Dentifrice, its method of manufacture and gargle
US4402941A (en) * 1981-09-15 1983-09-06 Marc Vaillancourt Veterinary composition for preventing feline urological syndrome and litter product containing the composition
US4548809A (en) * 1984-03-27 1985-10-22 Fung Paul S T Method for manufacturing a stomatic gargle
US4590065A (en) * 1985-04-18 1986-05-20 Colgate-Palmolive Company Stable flavor-containing dentifrice
WO1993016680A1 (en) * 1992-02-29 1993-09-02 Smithkline Beecham Plc Use of polyvinyl pyrrolidone for reducing the adherence of oral bacteria

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2426436A (en) * 1945-11-23 1947-08-26 David L Cochener Fluorescent lamp fixture

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB601801A (en) * 1945-12-03 1948-05-12 Lakeland Foundation Improvements relating to oral cleansing preparations and methods of making the same

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE873891C (de) * 1944-07-27 1953-04-20 Basf Ag Kosmetische Zubereitungen

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB601801A (en) * 1945-12-03 1948-05-12 Lakeland Foundation Improvements relating to oral cleansing preparations and methods of making the same

Cited By (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2471780A1 (fr) * 1979-12-19 1981-06-26 Colgate Palmolive Co Composition de pate dentifrice
US4307076A (en) * 1979-12-19 1981-12-22 Colgate-Palmolive Company Toothpaste compositions
EP0051752A3 (en) * 1980-11-12 1983-02-09 Weilin Liau Dentifrice, its method of manufacture and gargle
US4402941A (en) * 1981-09-15 1983-09-06 Marc Vaillancourt Veterinary composition for preventing feline urological syndrome and litter product containing the composition
US4548809A (en) * 1984-03-27 1985-10-22 Fung Paul S T Method for manufacturing a stomatic gargle
US4590065A (en) * 1985-04-18 1986-05-20 Colgate-Palmolive Company Stable flavor-containing dentifrice
AT388667B (de) * 1985-04-18 1989-08-10 Colgate Palmolive Co Zahnpflegemittel
WO1993016680A1 (en) * 1992-02-29 1993-09-02 Smithkline Beecham Plc Use of polyvinyl pyrrolidone for reducing the adherence of oral bacteria
US5538714A (en) * 1992-02-29 1996-07-23 Smithkline Beecham Plc Use of polyvinyl pyrrolidone for reducing the adherence of oral bacteria

Also Published As

Publication number Publication date
DE966246C (de) 1957-07-18
NL185343B (nl)
BE526730A (en])
CH327917A (de) 1958-02-15
GB739936A (en) 1955-11-02
NL87045C (en])

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