US2519665A - Dentifrice - Google Patents
Dentifrice Download PDFInfo
- Publication number
- US2519665A US2519665A US53156A US5315648A US2519665A US 2519665 A US2519665 A US 2519665A US 53156 A US53156 A US 53156A US 5315648 A US5315648 A US 5315648A US 2519665 A US2519665 A US 2519665A
- Authority
- US
- United States
- Prior art keywords
- methyl salicylate
- dentifrice
- sodium
- powder
- flavoring
- 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.)
- Expired - Lifetime
Links
- 239000000551 dentifrice Substances 0.000 title claims description 17
- OSWPMRLSEDHDFF-UHFFFAOYSA-N methyl salicylate Chemical compound COC(=O)C1=CC=CC=C1O OSWPMRLSEDHDFF-UHFFFAOYSA-N 0.000 claims description 36
- 239000000843 powder Substances 0.000 claims description 21
- 229960001047 methyl salicylate Drugs 0.000 claims description 15
- 239000004615 ingredient Substances 0.000 claims description 13
- 239000000796 flavoring agent Substances 0.000 claims description 8
- 235000019634 flavors Nutrition 0.000 claims description 8
- -1 ALKALI METAL SALT Chemical class 0.000 claims description 3
- 229910052783 alkali metal Inorganic materials 0.000 claims description 3
- QKEBHWZTVCFHCF-UHFFFAOYSA-M sodium;2-methoxycarbonylphenolate Chemical compound [Na+].COC(=O)C1=CC=CC=C1[O-] QKEBHWZTVCFHCF-UHFFFAOYSA-M 0.000 description 10
- 239000000463 material Substances 0.000 description 7
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 238000005498 polishing Methods 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- 235000007297 Gaultheria procumbens Nutrition 0.000 description 4
- 241000736246 Pyrola Species 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 239000003463 adsorbent Substances 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- YGUMNXUBAJCWHV-UHFFFAOYSA-L [Na+].[Na+].[O-]S([O-])(=O)=O.CCCCCCCCCCCC(=O)OCC(O)CO Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O.CCCCCCCCCCCC(=O)OCC(O)CO YGUMNXUBAJCWHV-UHFFFAOYSA-L 0.000 description 2
- 230000032683 aging Effects 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L calcium carbonate Substances [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- 239000001506 calcium phosphate Substances 0.000 description 2
- 229910000389 calcium phosphate Inorganic materials 0.000 description 2
- 235000011010 calcium phosphates Nutrition 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- HCWCAKKEBCNQJP-UHFFFAOYSA-N magnesium orthosilicate Chemical group [Mg+2].[Mg+2].[O-][Si]([O-])([O-])[O-] HCWCAKKEBCNQJP-UHFFFAOYSA-N 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- CVHZOJJKTDOEJC-UHFFFAOYSA-N saccharin Chemical compound C1=CC=C2C(=O)NS(=O)(=O)C2=C1 CVHZOJJKTDOEJC-UHFFFAOYSA-N 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 2
- LDVVTQMJQSCDMK-UHFFFAOYSA-N 1,3-dihydroxypropan-2-yl formate Chemical class OCC(CO)OC=O LDVVTQMJQSCDMK-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 244000246386 Mentha pulegium Species 0.000 description 1
- 235000016257 Mentha pulegium Nutrition 0.000 description 1
- 235000004357 Mentha x piperita Nutrition 0.000 description 1
- BPQQTUXANYXVAA-UHFFFAOYSA-N Orthosilicate Chemical compound [O-][Si]([O-])([O-])[O-] BPQQTUXANYXVAA-UHFFFAOYSA-N 0.000 description 1
- 101100313003 Rattus norvegicus Tanc1 gene Proteins 0.000 description 1
- 235000007303 Thymus vulgaris Nutrition 0.000 description 1
- 240000002657 Thymus vulgaris Species 0.000 description 1
- 239000002250 absorbent Substances 0.000 description 1
- 230000002745 absorbent Effects 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 125000002877 alkyl aryl group Chemical group 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 description 1
- 239000004327 boric acid Substances 0.000 description 1
- 239000007853 buffer solution Substances 0.000 description 1
- 229910000019 calcium carbonate Inorganic materials 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 235000021183 entrée Nutrition 0.000 description 1
- 150000002191 fatty alcohols Chemical class 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 235000001050 hortel pimenta Nutrition 0.000 description 1
- ZLNQQNXFFQJAID-UHFFFAOYSA-L magnesium carbonate Chemical compound [Mg+2].[O-]C([O-])=O ZLNQQNXFFQJAID-UHFFFAOYSA-L 0.000 description 1
- 239000001095 magnesium carbonate Substances 0.000 description 1
- 229910000021 magnesium carbonate Inorganic materials 0.000 description 1
- 239000000391 magnesium silicate Substances 0.000 description 1
- 229910052919 magnesium silicate Inorganic materials 0.000 description 1
- 235000019792 magnesium silicate Nutrition 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 239000000123 paper Substances 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 1
- 229940088417 precipitated calcium carbonate Drugs 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 210000003296 saliva Anatomy 0.000 description 1
- 239000000344 soap Substances 0.000 description 1
- 150000003385 sodium Chemical class 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000001585 thymus vulgaris Substances 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 239000009637 wintergreen oil Substances 0.000 description 1
Classifications
-
- 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
- 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
- A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
- A61K8/37—Esters of carboxylic acids
Landscapes
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Oral & Maxillofacial Surgery (AREA)
- Emergency Medicine (AREA)
- Birds (AREA)
- Epidemiology (AREA)
- Cosmetics (AREA)
Description
fiatentecl Aug. 22, 1 950 DENTIFRICE r Andrew August Klippert, Hollis, N. Y., assignor to Colgate-Palmclive-Peet Company,
Jersey City, N. J a corporation of Delaware N Drawing. Application October 6, 1948, Serial No. 53,156
9 Clairns.
l This invention relates to improvements in den tifrice compositions, and more particularly to improved flavoring material for powder dentifrices.
In flavoring dentifrices, oil of Wintergreen,
which is essentially methyl salicylate, has been frequently used. Instead of employing the natural oil itself, synthetic methyl salicylate has been utilized, but both the natural and the synthetic product are quite volatile. Accordingly, it
. has been necessary heretofore to package tooth 'powders which contain such volatile flavoring material in metal containers, since ordinary cardboard or paper receptacles cannot be satisfactorily employed because they are relatively porous and permit the volatile flavoring substance to escape too rapidly. Even with the use of metal containers there is a certain gradual loss of the volatile flavoring material through the top closure and the side seams, which are generally not made vapor tight. 'This loss may become sufficient, where the package is stored over a period of years before use, to impair the quality of the product. This, of course, is undesirable.
It has now been discovered that the wintergreen-type flavor may be prepared and used in a dry solid form, and which is not volatile and evanescent, the alkali metal derivative, i. e. sodium methyl salicylate is particularly effective for this purpose. and hence is not dissipated through the walls of a container, but remains in the dentifrice until used. During use, the mild acids of the saliva dissolve and convert the sodium methyl salicylate to free methyl salicylate which imparts thereupon the typical fresh pleasant Wintergreen flavor at the point of use. Suitable mixtures of the nonvolatile flavoring substance and volatile flavoring substances may be used to give the tooth powder a pleasing scent.
Sodium methyl salicylate may be prepared in any suitable manner. For example, the methyl salicylate salt may be made by reacting methyl salicylate with sodium hydroxide in alcohol solution. The desired sodium derivative of methyl salicylate formedby the reaction maybe recovered from the solution by crystallization. Where the potassium salt is desired, potassium hydroxide will be used in place of sodium hydroxide, as will be readily understood.
The following specific examples are given to show how the invention may be utilized, the examples being merely illustrative and not limitative of the invention.
This material is non-volatile Example I A tooth powder is made up containing the following ingredients:
Parts by Wt.
Di calcium phosphate 92.0 saccharine 0.1 Sodium glyceryl monolaurate sulfate 5.0 Sodium methyl salicylate 3.0
The ingredients, in finely divided form, are mixed together in a suitable mixing apparatus and are then packaged in ordinary cardboard containers.
Upon aging a portion of the dentifrice powder of Example I at approximately 105 F. for two weeks in an ordinary cardboard container, the tooth powder. at the end of the test period still possessed 'a pleasant Wintergreen flavor when used in the customary Way. Moreover, the tooth powder remained in the same dry, powdery state as when originally made. A similar dentifrice powder, however, in which 2 parts of methyl salicylate replaced 3 parts of sodium methyl salicylate, upon testing after a like aging period, was found to possess practically no flavoring, and was quite unpalatable.
As modifications of the tooth powder composition of Example I, the following is given:
Example II A soap base tooth powder is made up by thorougly mixing the following ingredients:
The ingredients in finely powdered form were thoroughly mixed to provide a powder-like soapbase dentifrice.
The ingredients were finely divided and thoroughly admixed to provide a finished tooth powder.
Example IV Parts by Wt. Di calcium phosphate 88.0 Saccharine 0.1 Sodium glyceryl monolaurate sulfate 5.0 Sodium methyl salicylate 2.0
Magnesium carbonate Methyl salicylate 1.0
The ingredients of (B) are thoroughly-mixed and added to ingredients (A), and the hole suitably mixed. The methyl salicylate is incorporated to give the tooth powder a pleasing odor of Wintergreen during the normal period of storage. When the dentifrice is used the flavor fortified through the dissolving and conversion of This is .111 adsorbent silicate of the dehydrated activated gel type, a similar product being sold under the i ew e s q mi fidt d TIhe ingredients of 1B) are thoroughly mixed and added to ingredients .(A), and the whole Suitably mixed. The precipitated magnesium silicate functions to .adsorb and release slowly :the methyl salicylate so that the .dentrifice pow- ;der has a pleasing aroma of Wintergreen fora :much longer timethan where no adsorbent pow- ,der, .is used. Other suitable adsorbent .or absorbent substances maybe used in place of or together with the precipitated magnesium silicate. For exampl'acolloidalclay, activated carbon or the like may be used for-this purpose.
.Qther .volatile flavoring substances also may be used. with the sodium methyl salicylate if :desired, such as oil of peppermint, thyme or the like, and which give the dentifrice a pleasing spent over the-normal period Of storage and use.
Various wetting agents, such as alkyl aryl sulpl'ronates or the like, may be used in place of the sulfated fatty alcohol or monoglyceride type compounds. Also other fillers and/or cleansing and polishing agents "commonly used ingthe preparation of tooth powders may be incorporatedor substituted in Whfile "or in-part for equivalent materials mentioned in'the examples. q For instance, in place of 'di-calcium carbonate there may bensed-tricalcium.ortho phosphate. Also precipitated calcium carbonate and/or magnesium carbonate may be used as a polishing agent, either alone or in combination. In addition, an acid buffer, such as boric acid may be incorporated, if desired to aid in liberating the methyl salicylate during use of the dentrifice. It will be also understood that other flavoring materials may be used with sodium methyl salicylate to modify its flavor. Coloring materials and the like may also be added in varying amounts to produce a tooth powder having the desired physical characteristics.
While the use of sodium methyl salicylate is preferred, it is to be understood that other water soluble methyl salicylate compounds may be used which are non-toxic and release methyl salicylate during the use of the powder, and such modifications of the dentifrice powder compositions are considered to be within the scope of the present invention.
What is claimed and desired to be protected by Letters Patent is:
1. A dentifrice tooth powder containing as a flavor imparting ingredient, an alkali metal salt of methyl salicylate.
2,.A' dentifrice tooth pbWderpontaining as a flavor imparting ingredient, a sodium salt of methyl salicylate.
3. A dentifrice tooth powder comprising a polishing agent, vSodium methyl salicylate and methyl salicylate.
' 51:. A dentifrice tooth powder comprising as a polishing agent a phosphate salt, and sodium methyl salicylate as a flavoring ingredient.
. A d nti e too h. PQWd pmpr s V polis in a n a d rg nt eqdi m methyl salic a and a ol ti lev fi e m r l- .s. A d ri e to t eewd r compri in e fi rc -imp t n in re ients t em t en of a s i nonolat e substan e s mp' i a alkali m t se pf. ei. v. s c l e wh h eom os s i Wvi r medi ne a a m ie ie ep l uid wha e Flavoring ie p 7. A dentifr e tooth powder as ,claimed in the preceding ,cl m wherein there is included an e he l eni we e: e ai 'ifi w re flavoring ub tanc to. lengthen the time that said liq- .416 new fi ei ee se am em s n entree 8- ,A sien j iri e th iwwd r cqmprismg an I et ri teet ew w ta n 1 en 5 for cleansing and polishing teeth,a .e e i a or 'se l ieg hf m fi n an a a m ta sa t .q m th l sali ate ANDR W AU UST K IPPEB a 1:53pm: us ng-{Es CITED UNITED STATES PATENTS n 7 Name Date 2,216,821 Long Oct. 8, 1940 'FQBBIQN PATENTS Numb r .xfi nnztrv Da 472,812. Great rita n S t. :23. 19.3
Claims (1)
1. A DENTIFRICE TOOTH POWDER CONTINING AS A FLAVOR IMPARTING INGREDIENT, AN ALKALI METAL SALT OF METHYL SALICYLATE.
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US53156A US2519665A (en) | 1948-10-06 | 1948-10-06 | Dentifrice |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US53156A US2519665A (en) | 1948-10-06 | 1948-10-06 | Dentifrice |
Publications (1)
Publication Number | Publication Date |
---|---|
US2519665A true US2519665A (en) | 1950-08-22 |
Family
ID=21982295
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US53156A Expired - Lifetime US2519665A (en) | 1948-10-06 | 1948-10-06 | Dentifrice |
Country Status (1)
Country | Link |
---|---|
US (1) | US2519665A (en) |
Cited By (10)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2647073A (en) * | 1951-04-13 | 1953-07-28 | Amm I Dent Inc | Ammoniated dentifrice containing anhydrous dicalcium phosphate |
US2773801A (en) * | 1952-07-03 | 1956-12-11 | Colgate Palmolive Co | Dentifrice compositions comprising a normally-solid water soluble condensation product of ethylene glycol and polypropylene glycol |
US2812284A (en) * | 1953-04-15 | 1957-11-05 | Procter & Gamble | Oral detergent composition and dentifrice comprising same |
US3137632A (en) * | 1952-02-19 | 1964-06-16 | Colgate Palmolive Co | Chlorophyll dentifrice compositions |
US3449266A (en) * | 1964-05-25 | 1969-06-10 | Drackett Co | Stabilized solid granular perfume composition |
US4547362A (en) * | 1983-03-14 | 1985-10-15 | Church & Dwight Co., Inc. | Sodium-bicarbonate-containing tooth powder |
US4623536A (en) * | 1985-06-13 | 1986-11-18 | Church & Dwight Co., Inc. | Sodium bicarbonate containing toothpaste |
US4663153A (en) * | 1983-03-14 | 1987-05-05 | Church & Dwight Co., Inc. | Sodium bicarbonate-containing tooth powder |
US5514366A (en) * | 1993-04-07 | 1996-05-07 | Diamond; Jeffrey H. | Dental and oral preparation for smokers for solubilizing and removing tobacco tars as well as onion and garlic essential oils |
US6086372A (en) * | 1997-06-04 | 2000-07-11 | Block Drug Company, Inc. | Dental and oral preparation |
Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
GB472812A (en) * | 1935-02-06 | 1937-09-30 | Pepsodent Company | Improved dentrifice |
US2216821A (en) * | 1938-11-04 | 1940-10-08 | Pepsodent Co | Dentifrice |
-
1948
- 1948-10-06 US US53156A patent/US2519665A/en not_active Expired - Lifetime
Patent Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
GB472812A (en) * | 1935-02-06 | 1937-09-30 | Pepsodent Company | Improved dentrifice |
US2216821A (en) * | 1938-11-04 | 1940-10-08 | Pepsodent Co | Dentifrice |
Cited By (12)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2647073A (en) * | 1951-04-13 | 1953-07-28 | Amm I Dent Inc | Ammoniated dentifrice containing anhydrous dicalcium phosphate |
US3137632A (en) * | 1952-02-19 | 1964-06-16 | Colgate Palmolive Co | Chlorophyll dentifrice compositions |
US2773801A (en) * | 1952-07-03 | 1956-12-11 | Colgate Palmolive Co | Dentifrice compositions comprising a normally-solid water soluble condensation product of ethylene glycol and polypropylene glycol |
US2812284A (en) * | 1953-04-15 | 1957-11-05 | Procter & Gamble | Oral detergent composition and dentifrice comprising same |
US3449266A (en) * | 1964-05-25 | 1969-06-10 | Drackett Co | Stabilized solid granular perfume composition |
US4547362A (en) * | 1983-03-14 | 1985-10-15 | Church & Dwight Co., Inc. | Sodium-bicarbonate-containing tooth powder |
US4663153A (en) * | 1983-03-14 | 1987-05-05 | Church & Dwight Co., Inc. | Sodium bicarbonate-containing tooth powder |
US4623536A (en) * | 1985-06-13 | 1986-11-18 | Church & Dwight Co., Inc. | Sodium bicarbonate containing toothpaste |
US4721614A (en) * | 1985-06-13 | 1988-01-26 | Church & Dwight Co., Inc. | Sodium bicarbonate containing toothpaste |
US5514366A (en) * | 1993-04-07 | 1996-05-07 | Diamond; Jeffrey H. | Dental and oral preparation for smokers for solubilizing and removing tobacco tars as well as onion and garlic essential oils |
US5662888A (en) * | 1993-04-07 | 1997-09-02 | Jeffrey Mitchell Laboratories | Toothpaste for smokers for solubilizing and removing tobacco tars |
US6086372A (en) * | 1997-06-04 | 2000-07-11 | Block Drug Company, Inc. | Dental and oral preparation |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
US2519665A (en) | Dentifrice | |
ES2249808T3 (en) | COMPOSITION DECOLORANTE FOR THE HAIR. | |
US4180467A (en) | Stable denture soak product | |
US4980154A (en) | Tooth and gum dentifrice composition and method of making same | |
US5041280A (en) | Toothpaste composition for stain removal | |
CA1339086C (en) | Compositions for preventing tooth decay | |
US3475533A (en) | Water-free toothpastes containing metaphosphates,calcium carbonate,and mineral oil | |
US2216816A (en) | Dentifrice | |
US2128917A (en) | Tooth paste | |
US4690776A (en) | Method of manufacture of a toothpaste composition | |
US1435498A (en) | Dentifrice | |
US4292028A (en) | Cosmetic breath freshener and palate coolant composition and method of use | |
JP2002114657A (en) | Base material for composition for oral cavity and composition for oral cavity | |
US2090437A (en) | Dentifrice | |
JP4142571B2 (en) | Preparation method of toothpaste using sorbitol syrup | |
JPS61100516A (en) | Toothpaste sealed in gelatin capsule | |
JPS58208205A (en) | Dental cement containing polyvinyl butyral as additive | |
US1861189A (en) | Dentifrice | |
US2042359A (en) | Dentifrice | |
JPS649241B2 (en) | ||
US4165366A (en) | Dental prophylactic paste | |
US2701212A (en) | Germicidal deodorizing dental adhesive and a method of making same | |
US3010834A (en) | Impression compound | |
BR112020020818A2 (en) | WASH COMPOSITION | |
JP3241946B2 (en) | Oral composition |