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WO2001058415A1 - Composition de dentifrice - Google Patents

Composition de dentifrice Download PDF

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Publication number
WO2001058415A1
WO2001058415A1 PCT/IB1999/001488 IB9901488W WO0158415A1 WO 2001058415 A1 WO2001058415 A1 WO 2001058415A1 IB 9901488 W IB9901488 W IB 9901488W WO 0158415 A1 WO0158415 A1 WO 0158415A1
Authority
WO
WIPO (PCT)
Prior art keywords
carrageenan
viscosity
guar
toothpaste composition
iota
Prior art date
Application number
PCT/IB1999/001488
Other languages
English (en)
Inventor
Harris J. Bixler
Grecilda Sanchez-Zaballero
Original Assignee
Shemberg Marketing Corporation
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
Application filed by Shemberg Marketing Corporation filed Critical Shemberg Marketing Corporation
Priority to PCT/IB1999/001488 priority Critical patent/WO2001058415A1/fr
Priority to AU52987/99A priority patent/AU5298799A/en
Publication of WO2001058415A1 publication Critical patent/WO2001058415A1/fr

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Classifications

    • 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
    • A61K8/73—Polysaccharides
    • 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
    • A61K8/73—Polysaccharides
    • A61K8/737—Galactomannans, e.g. guar; Derivatives thereof
    • 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
    • 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
    • A61K2800/59—Mixtures
    • A61K2800/594—Mixtures of polymers

Definitions

  • Carrageenan is a linear-sulfated polysaccharide of D-galactose and 3,6 anhydro-D-galactose (3.6 AG) which is extracted from red seaweed (Rhodophyceae) .
  • Commercially available carrageenans are essentially ground, dehydrated gels containing approximately 12% water. These materials can viscosify or gel a system into which they are incorporated. Rheological properties of the carrageenan depend upon the nature and quantity of the carrageenan, as well as the inclusion of other components (particularly salts and polyols) in the formulation.
  • Carrageenan has been used as a toothpaste binder, but its application is limited due to the fact that the cost of this ingredient is relatively high as compared with alternative binders.
  • CMC carboxymethyl cellulose
  • CMC carboxymethyl cellulose
  • the cost of CMC is less than 1/2 the cost of the carrageenan reagent.
  • the present invention relates to a cellulase-resistant toothpaste composition
  • a cellulase-resistant toothpaste composition comprising ultra low viscosity guar and carrageenan as a combination viscosity builder. Because ultra low viscosity guar is less expensive than carrageenan, the combination offers cost saving potential.
  • the combination viscosity builder comprises less than about 10% of the toothpaste composition by weight, and more preferably, about 0.5% to about 5% of the toothpaste composition by weight.
  • the low viscosity guar preferably comprises less than about 50% of the combination viscosity builder by weight, and more preferably, about 20% to about 30% of the combination viscosity builder by weight.
  • Formulations wherein the carrageenan component comprises a mixture of iota and lambda carrageenan types yield excellent results.
  • the preferred iota carrageenan type is produced as an approximately 100 mesh size calcium salt or mixed calcium and sodium salt (greater than 95% through a 100 mesh screen) .
  • the preferred lambda carrageenan type is produced as an approximately 100 mesh size sodium salt.
  • a toothpaste produced according to present specification will have a toothpaste viscosity rating of between about 20-35 BKU (Brookfield helipath viscometer) .
  • the strength of the paste as determined by the Cuban rating will be between 6 and 9.
  • the present invention also relates to a dry blend comprising about 20-30% low viscosity guar, about 50-60% iota-type carrageenan and about 20-30% lambda-type carrageenan.
  • the specifications which relate to these components of the dry blend are identical to those discussed above in connection with the toothpaste composition.
  • the dry blend when appropriately hydrated, has a water viscosity of at least about 40 cps (1.5% dry blend in distilled water at 75° C.)
  • Fig. 1 is a diagrammatic representation of a hydration profile determination for 1) ULV guar (2% ULV 200) , 2) 2% iota carrageenan (2% iota) , and 3) 2% iota carrageenan and 2% ULV guar (2% iota + 2% ULV) in a solution comprising 1:1 water : glycerin, 1% NaCl .
  • FIG. 2 is a diagrammatic representation of a hydration profile determination for 1) ULV guar (guar LM) , 2) lambda carrageenan, and 3) 1% lambda carrageenan and 1% ULV guar in a solution comprising 1:1 water :glycerin, 1% NaCl .
  • Fig. 3 is a diagrammatic representation of a hydration profile determination for 1) 2% silica, 2) 2% silica and 2% iota carrageenan, and 3) 2% iota carrageenan in a solution comprising 1:1 water : glycerin, 1% NaCl.
  • Fig. 4 is a diagrammatic representation of a hydration profile determination for 1) 20% lambda carrageenan, 60% iota carrageenan and 20% silica; and 2) 20% lambda carrageenan, 60% iota carrageenan and 20% ULV guar in a solution comprising 1:1 water :glycerin, 1% NaCl.
  • Toothpastes generally contain the following components: an abrasive, such as dicalcium phosphate or chalk (calcium carbonate) ; a humectant such as glycerine, sorbitol, or polyethylene glycol 600; water between 20-35%; salts; sweetener (e.g. sodium saccharine); color and flavor oil; and a binding reagent. Binding reagents are included in a toothpaste composition to build viscosity.
  • an abrasive such as dicalcium phosphate or chalk (calcium carbonate)
  • a humectant such as glycerine, sorbitol, or polyethylene glycol 600
  • water between 20-35% salts
  • sweetener e.g. sodium saccharine
  • color and flavor oil e.g. sodium saccharine
  • Binding reagents are included in a toothpaste composition to build viscosity.
  • Natural and synthetic gums and gum- like materials have been used as binding agents, including, for example, Irish moss (carrageenan) , gum guar, gum tragacanth, carboxymethyl cellulose, hydroxyethyl cellulose, polyvinyl pyrrolidone, starch, xanthan, or water-soluble hydrophilic colloidal polymers and synthetic inorganic silicated clays.
  • the binder content typically employed is in an amount up to about 10% by weight, and preferably about 0.5-5% of the formulation. Toothpaste compositions are discussed generally in U.S. Patent Nos .
  • the present invention relates to a toothpaste composition
  • a toothpaste composition comprising Ultra Low Viscosity (ULV) guar gum and carrageenan as a combination viscosity builder.
  • the combination viscosity builder preferably comprises less than about 10% of the toothpaste composition by weight, the most preferred range being from about 0.5% to about 5% of the toothpaste composition by weight.
  • ULV guar gum is derived from a highly purified extract of Guar seeds " Cyanopsis tetragonolobus" , a plant native to India.
  • ULV guar gum is a cold water soluble polysaccharide galactommanans, having a mannose to galactose ratio of approximately 2:1.
  • the molecular weight of native gum guar is in the 180,000 to 220,000 range.
  • Normal guar gum has excessive viscosity and a gummy texture which precludes its use in many food products and toothpaste.
  • the development of ultra low viscosity guar gum allows for its use in products previously limited to using other hydrocoloids .
  • ULV guar gum is highly depolymerized and the molecular weight is substantially lower than that of the native compound. Depolymerization is typically effected through a thermal and mechanical degradation technique. Useful natural features of the guar gum are retained through this process. For example, no detectable etherification or esterification takes place so cold water solubility is retained.
  • the ultra low viscosity guar used as a component of the combination viscosity builder has a water viscosity rating of from about 200 cps to about 500 cps, the most preferred ULV guar viscosity being about 200 cps and the powder is approximately 100 mesh size.
  • Viscosity determinations on guar are conventionally made using a viscometer, such as a Brookfield viscometer at a gum concentration of 1.5 % in water at 25° C.
  • the carrageenans comprise a family of linear sulfated food grade polysaccharides isolated rom red seaweeds or marine algae . Carrageenans have been used in toothpaste compositions world-wide for more than 50 years.
  • carrageenan types There are three major carrageenan types (kappa, iota and lambda) , all having the ability to build viscosity, with kappa and iota able to form a variety of gels.
  • the various members of the carrageenan family differ from one another in 3 , 6-anhydro-D-galactose content and the number and position of ester sulfate groups.
  • Carrageenans are highly negatively charged and are isolated as salts (e.g., ammonium, calcium, potassium, and sodium salts) .
  • carrageenans can be exploited in toothpaste to provide a continuous phase gel matrix thereby enhancing viscosity stabilization and providing emulsion stability by trapping additives such as abrasives and flavor oils.
  • specific interactions between carrageenan and the surface of abrasives both disperse and stabilize solids preventing hardening, caking, and drying out.
  • the mixture of carrageenan types used affects paste viscosity, paste strength, and paste consistency.
  • preferred embodiments comprise a blend of iota and lambda carrageenan types which yield a smooth, soft paste which is preferred by consumers.
  • the characteristics of the carrageenan varieties which are relevant in this application are shown in Table 1.
  • lambda carrageenan preparations contain a certain amount of a very weak gelling kappa carrageenan (kappa-2) .
  • kappa-2 very weak gelling kappa carrageenan
  • the iota and lambda carrageenans used in connection with the present invention are isolated and prepared using conventional techniques. It is further preferred that the iota variety be prepared as a calcium salt or a mixture of sodium and calcium salts, to control its hydration and limit its reactivity with the abrasive of choice, either dicalcium phosphate or chalk. It is further preferred that the lambda variety be prepared as a sodium salt to enhance its cold hydration. Alternative salts of carrageenan have been tested but determined to be less well suited for toothpaste applications. Toothpaste formulations contain various amounts of fluorides, phosphates, benzoate, sulfates, and saccharin with their respective cations.
  • the cation form of the iota and lambda carrageenans must be carefully selected and controlled.
  • a sodium salt of iota carrageenan has been tested in a toothpaste application. It was determined that the sodium iota carrageenan tended to produce a toothpaste that hardened with time because mobile calcium ions present in the abrasive (either dicalcium phosphate or chalk) gradually displaced the sodium ions of sodium iota carrageenan, converting it to the stronger gelling calcium iota carrageenan salt.
  • the iota and lambda forms of carrageenan are prepared by conventional techniques.
  • the lambda variety is prepared as the sodium salt from Chilean red marine algae, e.g. Gigartina radula and Gigartina skottsbergii .
  • the Canadian red marine algae Chondrus crispus, or Irish moss can be substituted for the Chilean marine algae, albeit at a penalty of higher cost.
  • the algae is harvested, cleaned, dried, baled and shipped to a processing plant. At the plant, the harvested algae is washed, macerated and extracted in a hot alkaline solution (in this case sodium hydroxide) . The mix is then filtered through a filter-press which removes cellulose and other insolubles from the carrageenan solution.
  • the product solution is then neutralized with dilute hydrochloric acid and concentrated by either drum-drying or through alcohol precipitation which removes. soluble color bodies and some inorganic salts.
  • the concentrated carrageenan is dried, ground and sieved through a sizing screen.
  • the calcium salt of the iota variety is prepared from the Eucheuma spinosum variety of red marine algae using a similar protocol where calcium hydroxide (lime) is used as the alkaline extraction medium rather than sodium hydroxide.
  • the sizing screen used to sieve the carrageenan preparations is 100 mesh. Carrageenan preparations sieved through less than 100 mesh screening yield a product which is overly course for the application in that a "lumpy" paste results. Sieving through a sizing screen of more than 100 mesh results in a product which is overly fine and which tends to result in a dusty environment in the formulation facility.
  • the Formulation I composition can be prepared on a small scale by dispersing a dry blend of the sodium saccharin, sodium benzoate, tetrasodium pyropyosphate, sodium monofluorophosphate, and combination viscosity builder into a beaker containing the glycerine. This is mixed for 5 minutes and then water is added. The mixture is heated to 65-71° C in a boiling water bath and the temperature held for 20 minutes, compensating for evaporated water loss. The mixture is then transferred to a Ross mixer. The dicalcium phosphate is added, using a spatula. The formulation is then mixed at speed 2 for 2 minutes, when the mixer is stopped and the bowl and blades are scraped.
  • the Formulation II composition can be prepared by heating the water to 65° C, and dispersing the combination viscosity builder into the water with stirring while gradually increasing stir speed to high, mixing for 10 minutes. Sorbitol is then added and mixed at medium speed for 15 minutes. A dry blend of sodium saccharin, tetrasodium pyrophosphate, monofluorophosphate, and sodium benzoate is slowly added to the mixture. The mixture is heated to 65-71° C with stirring at medium to high speed for 15 minutes in a boiling water bath, compensating for water lost to evaporation. The mixture is transferred to a Ross mixer, the chalk is added and mixed for 5 minutes at speed 3.
  • the mixer is stopped and the bowl and blades are scraped before further mixing for 20 minutes at speed 5 with a vacuum of not less than 28 inches Hg.
  • the sodium lauryl sulfate and flavor oils are added and mixed in for 5 minutes at speed 3 under vacuum.
  • scale up is a matter of routine experimentation.
  • the toothpaste compositions of the present mixture has an overall viscosity rating from about 20 BKU to about 35 BKU (Brookfield helipath units) Brookfield toothpaste viscosity ratings are determined by the following procedure using Brookfield equipment manufactured by Brookfield Engineering Laboratories, Stoughton, MA. The equipment includes a Brookfield RVT dial viscometer, a Brookfield Helipath
  • the toothpaste compositions of the present invention also are characterized as having a Cuban rating from about 6 to about 9.
  • Cuban ratings are determined using a Cuban tester, a standardized nozzle, and the paste under evaluation at room temperature.
  • the tube of cream is held one to three inches above the tester and squeezed firmly to start the flow.
  • the tube is passed evenly over the tester from end to end at a moderate speed (2-4 seconds) , and timing begins when the cream ribbon touches the end opposite the one from which the ribbon started.
  • Consistency is determined by counting the intervals in which the cream is unbroken after 30 seconds for each ribbon and taking their average .
  • Ten seconds after the start of the stop watch a second ribbon is extruded and timed after it reaches the opposite end of the tester. Care must be taken to prevent the cream ribbons from forming large loops between the bars. This can be accompanied by increasing the speed at which the cream is moved over the tester.
  • the hydration profile for the 2% iota carrageenan/2% ULV guar exhibited substantial hydration synergy, peaking at about 3,200 Brabender units.
  • the hydration profile for the 2% lambda carrageenan/2% ULV guar also exhibited substantial hydration synergy, peaking at about 2,800 Brabender units, compared to 2% lambda carrageenan alone whose synergy peaked at around 900 Brabender units, shown in Fig. 2.
  • a control experiment provides no indication of hydration synergy between carrageenan/silica combination viscosity builder (see Fig. 3) .
  • the viscosity peak generated from the combination of carrageenan and silica is essentially additive of the peaks generated by two independent components .
  • the present invention relates to a dry blend comprising about 20-30% low viscosity guar, about 50-60% iota-type carrageenan and about 20-30% lambda-type carrageenan.
  • the specification relating to these components of the dry blend are identical to those discussed above in connection with the combination viscosity builder.
  • the dry blend will typically be sold in bulk to companies engaged in toothpaste formulation. When a water solution viscosity is taken for purposes of quality control, the dry blend has a Brookfield water viscosity rating of at least about 40 cps.
  • Water viscosity is measured by the following procedure: 6 grams of sample is slowly dispersed into a beaker of 394 ml distilled water, with constant stirring. The weight of the beaker plus contents are determined. The solution is heated to 80° C with constant stirring and the temperature is maintained for 10 minutes. The beaker is reweighed and the resulting weight loss is compensated for by the addition of hot water. The solution is stirred and the temperature lowered until it reaches 75° C, where the viscosity is read with a preheated spindle. For a typical all carrageenan toothpaste viscosity builder (60% iota carrageenan, 40% lambda carrageenan) the water viscosity is 40 to 80 cps.
  • the experimental series described below was designed to monitor hydration effects using the combination binder of the present invention. Hydration effects were determined using a Brabender Viscograph. More specifically, the instrument employed was a VISCO/AMYLO/GRAPH model VA-VE PT-100 gelation viscometer, equipped with mechanical torque recorder, measuring bowl with stirrer and water cooled cover, and an electronic controller allowing for the evaluation of standard and complex tests of starch and starch-like products. The instrument stores up to five separate temperature programs, each consisting of a ramp, peak temperature, and a hold period. The heating and cooling rates of the instrument are 0.1° C to 4° C/min. The instrument also offers variable speed control up to 150 rpm.
  • the Brabender Viscograph is an excellent instrument for investigating the swelling and dissolution characteristics of hydrocolloids . Information gathered from the Brabender Viscograph has been shown to characterize the physical properties required by a toothpaste viscosity builder for production, and for finished product simulation of a toothpaste.
  • temperature and cation concentration essentially control the rate and extent of carrageenan hydration.
  • viscosity can be empirically related to hydration and swelling. During the swelling phase, viscosity increases to a maximum and then falls as the gum dissolves. Salts depress gum swelling and increase the temperature required for functionality (Tye, R. ;
  • the hydration of a carrageenan is determined by the gel potential of the carrageenan and the particle morphology.
  • Brabender hydration is a sensitive method for detecting changes in both gel potential and particle morphology.
  • the gel strength determination frequently used to characterize carrageenans, can not detect changes in particle morphology or ease of hydration. Hydration profiles were determined for guar/carrageenan and a silica/carrageenan control. The protocol employed for hydration determination was as follows.
  • total ion concentration e.g., sodium, potassium or calcium
  • elixir a term of art used in connection with dentifrice preparations referring to a gum/humectant/salt system prepared prior to abrasive addition
  • 1% NaCl was employed to simulate the ionic composition of the toothpaste formulation used herein.
  • the solution was prepared using 250 g distilled water at 10° C. 250 grams of the polyol glycerin was added to the solution. This polyol to water ratio is approximately that of the toothpaste formulation herein.
  • Fig. 1 is a chart showing the hydration profiles of ULV-200 guar, calcium salt of iota carrageenan (CI-100) and CI-100/ULV guar. The hydration profiles shown in Fig. 1 were generated using the following compositions:
  • Fig. 2 is a chart showing the hydration profiles of ULV-200 guar, sodium salt of lambda carrageenan (SL-100) and SL-100/ULV guar.
  • the hydration profiles shown in Fig. 2 were generated using the following compositions:
  • Fig. 3 is a chart showing the hydration profiles for the calcium salt of iota carrageenan (CI-100) , silica, and a CI-100/silica combination formulation.
  • the hydration profiles shown in Fig. 3 were generated using the following compositions:
  • Fig. 1 The hydration data in Fig. 1 clearly shows hydration synergy with iota carrageenan and ULV guar. More specifically, a Brabender unit determination for 2% ULV 200 alone was essentially 0. The hydration profile for 2% iota alone peaked at about 1,700 Brabender units. However, the hydration profile for the 2% iota/2% ULV guar exhibited substantial hydration synergy, peaking at about 3,200 Brabender units.
  • Fig. 3 provides no indication of hydration synergy between iota carrageenan and silica.
  • Silica alone and iota alone generated viscosity peaks of about 180 bu and 1450 bu respectively.
  • the combination of silica and iota produced merely an additive effect on viscosity, peaking at about 1640 bu, rather than the synergistic effect seen with ULV-guar and iota-carrageenan.
  • the combination of lambda carrageenan and silica also failed to exhibit synergy.
  • Fig. 4 shows hydration profiles for the preferred blend of iota and lambda carrageenan/ULV guar combination viscosity builder (labelled EC-9701 (ULV- 200) ) as compared to the hydration profile for an identical blend of carrageenans where the alternate binder silica has been substituted for ULV guar (labelled EC-9701 (silica)).
  • the hydration profiles in Fig. 4 were generated using the following gum blend compositions under conditions of 2% gum, 1:1 water : glycerine, 1% sodium chloride.
  • EC-9701 (ULV-200)
  • EC-9701 (silica) 20% sodium lambda 20% sodium lambda carrageenan carrageenan 60% calcium iota 60% calcium iota carrageenan carrageenan 20% ULV guar 200 20% silica
  • Fig. 4 demonstrates that the gum blend EC-9701 containing ULV guar generated higher viscosity than the gum blend containing the silica substitution, with the viscosity of the ULV-guar mix peaking at 770 Brabender units, and the silica mix peaking at 620 Brabender units.
  • Table 2 compares the toothpaste viscosities determined for different toothpaste products made with either the combination ULV-guar/carrageenan (20% ULV- Guar/60% CI-100, 20% SL-100) viscosity builder of the current invention, or the currently marketed carrageenan (60% CI-100, 40% SL-100) viscosity builder.

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  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
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Abstract

La présente invention concerne une composition de dentifrice comprenant un guar et un carragaheen à viscosité très basse en guise de renfort de combinaison de viscosité. Dans des modes de réalisation préférés de cette composition de dentifrice, ce renfort de combinaison de viscosité constitue moins de 10 % environ en masse de la composition de dentifrice totale, et de préférence, d'environ 0,5 % à environ 5 % en masse de cette composition. Le guar à basse viscosité constitue de préférence moins de 50 % environ en masse du renfort de combinaison de viscosité total, et mieux, d'environ 20 % à environ 30 % en masse du renfort de combinaison de viscosité total. Cette invention concerne aussi un mélange sec comprenant environ 20 % à 30 % de guar de basse viscosité, environ 50 % à 60 % de carragaheen de type iota et environ 20 % à 30 % de carragaheen de type lambda. Les spécifications relatives aux composants de ce mélange sec sont identiques à celles qui sont exposées ci dessus concernant cette composition de dentifrice. Ce mélange sec, lorsqu'il est convenablement hydraté, présente une viscosité humide d'au moins environ 40cps.
PCT/IB1999/001488 1999-08-17 1999-08-17 Composition de dentifrice WO2001058415A1 (fr)

Priority Applications (2)

Application Number Priority Date Filing Date Title
PCT/IB1999/001488 WO2001058415A1 (fr) 1999-08-17 1999-08-17 Composition de dentifrice
AU52987/99A AU5298799A (en) 1999-08-17 1999-08-17 Toothpaste composition

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Application Number Priority Date Filing Date Title
PCT/IB1999/001488 WO2001058415A1 (fr) 1999-08-17 1999-08-17 Composition de dentifrice

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Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4344931A (en) * 1980-12-18 1982-08-17 Abel Aguilar Dry dentifrice powders
US4453979A (en) * 1983-03-23 1984-06-12 Lever Brothers Company Dispersion of hydrophilic gums to form non-swelling aqueous alcoholic mixtures
US4702905A (en) * 1985-08-30 1987-10-27 Colgate-Palmolive Company Packaged dental cream
US5096698A (en) * 1987-10-08 1992-03-17 Colgate-Palmolive Company Packaged dental cream
US5869029A (en) * 1996-06-21 1999-02-09 Hercules Incorporated Dispersible water-soluble or water-swellable polymers and process for making toothpastes containing them

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4344931A (en) * 1980-12-18 1982-08-17 Abel Aguilar Dry dentifrice powders
US4453979A (en) * 1983-03-23 1984-06-12 Lever Brothers Company Dispersion of hydrophilic gums to form non-swelling aqueous alcoholic mixtures
US4702905A (en) * 1985-08-30 1987-10-27 Colgate-Palmolive Company Packaged dental cream
US5096698A (en) * 1987-10-08 1992-03-17 Colgate-Palmolive Company Packaged dental cream
US5869029A (en) * 1996-06-21 1999-02-09 Hercules Incorporated Dispersible water-soluble or water-swellable polymers and process for making toothpastes containing them

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