US3279068A - Method of detecting carious tissue - Google Patents
Method of detecting carious tissue Download PDFInfo
- Publication number
- US3279068A US3279068A US339608A US33960864A US3279068A US 3279068 A US3279068 A US 3279068A US 339608 A US339608 A US 339608A US 33960864 A US33960864 A US 33960864A US 3279068 A US3279068 A US 3279068A
- Authority
- US
- United States
- Prior art keywords
- tissue
- hydrochloride
- aminoacridine
- carious
- calculus
- 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
- 238000000034 method Methods 0.000 title claims description 8
- FTGPOQQGJVJDCT-UHFFFAOYSA-N 9-aminoacridine hydrochloride Chemical compound Cl.C1=CC=C2C(N)=C(C=CC=C3)C3=NC2=C1 FTGPOQQGJVJDCT-UHFFFAOYSA-N 0.000 claims description 7
- XJGFWWJLMVZSIG-UHFFFAOYSA-N 9-aminoacridine Chemical compound C1=CC=C2C(N)=C(C=CC=C3)C3=NC2=C1 XJGFWWJLMVZSIG-UHFFFAOYSA-N 0.000 claims description 3
- 229960001441 aminoacridine Drugs 0.000 claims description 3
- 239000000243 solution Substances 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 239000003755 preservative agent Substances 0.000 description 3
- FJKROLUGYXJWQN-UHFFFAOYSA-N 4-hydroxybenzoic acid Chemical compound OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 2
- 208000006558 Dental Calculus Diseases 0.000 description 2
- 206010044029 Tooth deposit Diseases 0.000 description 2
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 2
- DZBUGLKDJFMEHC-UHFFFAOYSA-N acridine Chemical compound C1=CC=CC2=CC3=CC=CC=C3N=C21 DZBUGLKDJFMEHC-UHFFFAOYSA-N 0.000 description 2
- 229960000686 benzalkonium chloride Drugs 0.000 description 2
- CADWTSSKOVRVJC-UHFFFAOYSA-N benzyl(dimethyl)azanium;chloride Chemical compound [Cl-].C[NH+](C)CC1=CC=CC=C1 CADWTSSKOVRVJC-UHFFFAOYSA-N 0.000 description 2
- OSASVXMJTNOKOY-UHFFFAOYSA-N chlorobutanol Chemical compound CC(C)(O)C(Cl)(Cl)Cl OSASVXMJTNOKOY-UHFFFAOYSA-N 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 239000008367 deionised water Substances 0.000 description 2
- 208000002925 dental caries Diseases 0.000 description 2
- 239000000499 gel Substances 0.000 description 2
- 235000010482 polyoxyethylene sorbitan monooleate Nutrition 0.000 description 2
- 229920000053 polysorbate 80 Polymers 0.000 description 2
- 230000000007 visual effect Effects 0.000 description 2
- JCIIKRHCWVHVFF-UHFFFAOYSA-N 1,2,4-thiadiazol-5-amine;hydrochloride Chemical compound Cl.NC1=NC=NS1 JCIIKRHCWVHVFF-UHFFFAOYSA-N 0.000 description 1
- 229940090248 4-hydroxybenzoic acid Drugs 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 1
- FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 description 1
- 235000014676 Phragmites communis Nutrition 0.000 description 1
- 241000277331 Salmonidae Species 0.000 description 1
- 229920001938 Vegetable gum Polymers 0.000 description 1
- 239000000443 aerosol Substances 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- 125000002091 cationic group Chemical group 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- 235000015218 chewing gum Nutrition 0.000 description 1
- 229960004926 chlorobutanol Drugs 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 229910021641 deionized water Inorganic materials 0.000 description 1
- 210000004268 dentin Anatomy 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 239000003589 local anesthetic agent Substances 0.000 description 1
- 229960005015 local anesthetics Drugs 0.000 description 1
- 239000007937 lozenge Substances 0.000 description 1
- 229920000609 methyl cellulose Polymers 0.000 description 1
- 239000001923 methylcellulose Substances 0.000 description 1
- 235000010981 methylcellulose Nutrition 0.000 description 1
- 229940096826 phenylmercuric acetate Drugs 0.000 description 1
- PDTFCHSETJBPTR-UHFFFAOYSA-N phenylmercuric nitrate Chemical compound [O-][N+](=O)O[Hg]C1=CC=CC=C1 PDTFCHSETJBPTR-UHFFFAOYSA-N 0.000 description 1
- 239000000244 polyoxyethylene sorbitan monooleate Substances 0.000 description 1
- 229940068968 polysorbate 80 Drugs 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 230000002335 preservative effect Effects 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 230000000472 traumatic effect Effects 0.000 description 1
- 238000009736 wetting Methods 0.000 description 1
- 239000000080 wetting agent 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
- A61K6/00—Preparations for dentistry
- A61K6/25—Compositions for detecting or measuring, e.g. of irregularities on natural or artificial teeth
-
- 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
- A61K8/4906—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with one nitrogen as the only hetero atom
- A61K8/4926—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with one nitrogen as the only hetero atom having six membered rings
-
- G—PHYSICS
- G01—MEASURING; TESTING
- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N33/00—Investigating or analysing materials by specific methods not covered by groups G01N1/00 - G01N31/00
- G01N33/48—Biological material, e.g. blood, urine; Haemocytometers
- G01N33/50—Chemical analysis of biological material, e.g. blood, urine; Testing involving biospecific ligand binding methods; Immunological testing
- G01N33/52—Use of compounds or compositions for colorimetric, spectrophotometric or fluorometric investigation, e.g. use of reagent paper and including single- and multilayer analytical elements
-
- 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
- A61K2800/42—Colour properties
- A61K2800/43—Pigments; Dyes
Definitions
- This invention relates to a method of detecting carious tissue and dental calculus.
- the present invention relates to a disclosing agent which makes a vivid contrast either in ordinary visual light or in ultraviolet light between sound dentin tissue and carious dentin tissue and also discloses the presence of calculus.
- 9-arninoacridine and its hydrochloride are unique agents for disclosing the presence of dental caries and calculus.
- the 9-aminoacridine or its hydrochloride stains differentially and has a distinctive dark brown color in the presence of carious tissue or calculus but has a light yellow color on sound tissue in either visual or ultraviolet light. Therefore, it is quite easy to distinguish between sound tissue and carious tissue or calculus.
- an aqueous solution of the 9-aminoacridine hydrochloride preferably utilizing deionized water.
- Solutions containing 9- aminoacridine hydrochloride and water in ratios of from 1:100 to 120,000 can be employed.
- compositions can be utilized in carrying out the invention.
- the base 9-aminoacridine itself can be dissolved in a 50-50 alcohol-water mixture and used instead of the hydrochloride.
- the compounds can also be incorporated in gels such as aqueous gels containing from 0.25% to 2.5% of methyl cellulose or vegetable gums, or can be incorporated in lozenges, chewing gums, aerosols or similar compositions.
- the Q-aminoacridine hydrochloride may be employed by itself as an aqueous solution, it is desirable in many instances to add additional agents such as nonionic or cationic surfiactants to increase its wetting ability or preservatives to increase the storage stability of sol-u- I tions after opening.
- Suitable wetting agents include henzalkonium chloride and polysorbate 80, U.S.P. (Tween 80), while suitable preservatives include benza-lkonium chloride, phenyl mercuric acetate, phenyl mercuric nitrate, chlorobutanol, esters of parahydroxy benzoic acid, and
- the solution is employed at a pH of trout 5 to 7 since at a higher 'pH the material tends to precipitate out of solution, while at a lower pH there is a traumatic elTe-ct on dental tissue.
- the material of the present invention is compatible with local anesthetics.
- the method of disclosing carious dentinal tissue and calculus comprising applying to a suspected area a small amount of a member selected irom the group consisting of 9-aminoacridine hydrochloride and 9+amin acridine.
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- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Hematology (AREA)
- Engineering & Computer Science (AREA)
- Immunology (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Oral & Maxillofacial Surgery (AREA)
- Urology & Nephrology (AREA)
- Epidemiology (AREA)
- Molecular Biology (AREA)
- Biomedical Technology (AREA)
- Chemical & Material Sciences (AREA)
- Biotechnology (AREA)
- Microbiology (AREA)
- Cell Biology (AREA)
- Birds (AREA)
- Biophysics (AREA)
- Food Science & Technology (AREA)
- Medicinal Chemistry (AREA)
- Physics & Mathematics (AREA)
- Analytical Chemistry (AREA)
- Biochemistry (AREA)
- General Physics & Mathematics (AREA)
- Pathology (AREA)
- Medicines Containing Antibodies Or Antigens For Use As Internal Diagnostic Agents (AREA)
Description
United States Patent 3,279,068 METHOD OF DETECTING CARIOUS TISSUE Marvin M. Stark, Los Altos, Calif., assignor to Barnes- Hind Pharmaceuticals, Inc, a corporation of California No Drawing. Filed Ian. 23, 1964, Ser. No. 339,608 3 Claims. (Cl. 167--84.5)
This invention relates to a method of detecting carious tissue and dental calculus.
In the preparation of teeth prior to filling, and in similar dental operations, it is highly important that all of the cations dentinal tissue be removed and that a minimum of sound dentinal tissue be removed. Since there can be little difference visually, between carious and sound tissue, it is often difiicult to make certain that all carious tissue is removed without the removal of an excessive amount of sound tissue. Similarly, it is advan- .tageous in cleaning teeth that calculus be disclosed.
The present invention relates to a disclosing agent which makes a vivid contrast either in ordinary visual light or in ultraviolet light between sound dentin tissue and carious dentin tissue and also discloses the presence of calculus.
In accordance with the present invention, it has been found that 9-arninoacridine and its hydrochloride are unique agents for disclosing the presence of dental caries and calculus.
In utilizing the compounds of this invention, it is only necessary to apply a small amount to the area in question. The 9-aminoacridine or its hydrochloride stains differentially and has a distinctive dark brown color in the presence of carious tissue or calculus but has a light yellow color on sound tissue in either visual or ultraviolet light. Therefore, it is quite easy to distinguish between sound tissue and carious tissue or calculus.
In accordance with a preferred method of carrying out the invention, it is only necessary to prepare an aqueous solution of the 9-aminoacridine hydrochloride, preferably utilizing deionized water. Solutions containing 9- aminoacridine hydrochloride and water in ratios of from 1:100 to 120,000 can be employed. However, it is generally preferred to prepare a relatively concentrated solution containing about one part of the 9-aminoacridine hydrochloride to 500 parts by weight of water.
Various other compositions can be utilized in carrying out the invention. Thus, the base 9-aminoacridine itself can be dissolved in a 50-50 alcohol-water mixture and used instead of the hydrochloride. The compounds can also be incorporated in gels such as aqueous gels containing from 0.25% to 2.5% of methyl cellulose or vegetable gums, or can be incorporated in lozenges, chewing gums, aerosols or similar compositions.
Although the Q-aminoacridine hydrochloride may be employed by itself as an aqueous solution, it is desirable in many instances to add additional agents such as nonionic or cationic surfiactants to increase its wetting ability or preservatives to increase the storage stability of sol-u- I tions after opening. Suitable wetting agents include henzalkonium chloride and polysorbate 80, U.S.P. (Tween 80), while suitable preservatives include benza-lkonium chloride, phenyl mercuric acetate, phenyl mercuric nitrate, chlorobutanol, esters of parahydroxy benzoic acid, and
the like. Generally speaking, it is preferred to package the solutions in a single usage container. In such instances, it is unnecessary to employ a preservative.
Preferably, the solution is employed at a pH of trout 5 to 7 since at a higher 'pH the material tends to precipitate out of solution, while at a lower pH there is a traumatic elTe-ct on dental tissue.
The following is a preferred composition:
0.2% by weight 9-arninoacrid-ine hydrochloride; 0.1% benzalkonium chloride; and 99.7% de-ionized water.
It is ordinarily not necessary to render such a solution isotonic, but if this is desired, adjustment should be made with non-ionizable materials such as glycerol, sorbitol, urea or the like.
The material of the present invention is compatible with local anesthetics.
The exact mechanism by which the present invention works is not understood. Many materials possess fluorescent properties yet have no value as disclosing agents.
I claim:
1. The method of disclosing carious dentinal tissue and calculus comprising applying to a suspected area a small amount of a member selected irom the group consisting of 9-aminoacridine hydrochloride and 9+amin acridine.
2. The method of claim 1 wherein an aqueous solution is utilized containing from 1:100 to 120,000 parts of 9- aminoacridine hydrochloride, the balance being water.
3. The method of claim 1 wherein a solution is utilized containing about 1 part of 9-aminoacridine hydrochloride to 500 parts water.
References Cited by the Examiner UNITED STATES PATENTS 2,151,495 3/ 1939 Bender 16793 References Cited by the Applicant UNITED STATES PATENTS 1,629,873 5/ 1927 Jensch. 1,760,781 5/ 1930 Schulemann et al. 1,766,403 6/ 1930 Schulemann et al. 1,889,704 11/ 1932 Schulem-ann et al. 2,092,131 9/ 1937 Mietzsch et all. 2,113,357 4/ 1938 Mietzsclh et al. 2,121,207 6/1938 Mietzsch et a1. 2,124,590 7/ 1938 Reed. 2,155,501 4/ 1939 Maiser. 2,334,348 11/ 1943 Miglarese. 2,488,904 11/1949 Falk. 2,531,010 11/ 1950 Surrey. 2,718,487 9/ 1955 Marx. 3,019,227 1/ 1962 Erner. 3,067,137 12/ 1962 Schmulling. 3, 122,553 2/ 1964 Seneca. 3,149,068 9/ 1964 Biedernran et al.
RICHARD A." GAUDET, Primary Examiner.
ROBERT E. MORGAN, Examiner.
Claims (1)
1. THE METHOD OF DISCLOSING CARIOUS DENTIAL TISSUE AND CALCULUS COMPRISING APPLYING TO A SUSPECTED AREA A SMALL AMOUNT OF A MEMBER SELECTED FROM THE GROUP CONSISTING OF 9-AMINOACRIDINE HYDROCHLORIDE AND 9-AMINOACRIDINE.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US339608A US3279068A (en) | 1964-01-23 | 1964-01-23 | Method of detecting carious tissue |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US339608A US3279068A (en) | 1964-01-23 | 1964-01-23 | Method of detecting carious tissue |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US3279068A true US3279068A (en) | 1966-10-18 |
Family
ID=23329817
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US339608A Expired - Lifetime US3279068A (en) | 1964-01-23 | 1964-01-23 | Method of detecting carious tissue |
Country Status (1)
| Country | Link |
|---|---|
| US (1) | US3279068A (en) |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3624219A (en) * | 1970-07-06 | 1971-11-30 | Max J Perlitsh | Plaque-disclosing composition and package system |
| US3903252A (en) * | 1972-06-08 | 1975-09-02 | Lorvic Corp | Dental disclosing compositions and the method of making and using the same |
| US4347233A (en) * | 1978-12-04 | 1982-08-31 | Kuraray Company, Limited | Dental caries detection |
| US4976951A (en) * | 1985-08-28 | 1990-12-11 | Melvyn Rosenberg | Dental caries diagnostic and localization technique |
| US5357989A (en) * | 1990-12-10 | 1994-10-25 | Naresh Gathani | Dental cleansing member |
Citations (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US1629873A (en) * | 1919-07-08 | 1927-05-24 | Ig Farbenindustrie Ag | Acridine derivatives and process of making same |
| US1760781A (en) * | 1926-12-20 | 1930-05-27 | Winthrop Chem Co Inc | Manufacture of new pharmaceutical products |
| US1766403A (en) * | 1930-06-24 | Weener schtjlemann | ||
| US1889704A (en) * | 1925-12-24 | 1932-11-29 | Winthrop Chem Co Inc | Compounds of the acridine series and process of making them |
| US2092131A (en) * | 1937-09-07 | S-of amino ackibines | ||
| US2113357A (en) * | 1930-05-09 | 1938-04-05 | Winthrop Chem Co Inc | Basically substituted amino-acridine derivatives |
| US2121207A (en) * | 1934-06-07 | 1938-06-21 | Winthrop Chem Co Inc | New basically substituted acridine compounds |
| US2124590A (en) * | 1934-11-09 | 1938-07-26 | Du Pont | Dye finishing process |
| US2151495A (en) * | 1937-04-05 | 1939-03-21 | David V Bender | Disclosing solution |
| US2155501A (en) * | 1936-04-11 | 1939-04-25 | Agfa Ansco Corp | Photographic treating bath |
| US2334348A (en) * | 1941-06-23 | 1943-11-16 | Nat Marking Mach Co | Sunburn preventive |
| US2488904A (en) * | 1945-03-03 | 1949-11-22 | Sterling Drug Inc | 1-methyl-5-aminoacridine and process for preparing it |
| US2531010A (en) * | 1949-01-22 | 1950-11-21 | Sterling Drug Inc | 9-[2-(2-hydroxyethylamino) ethylamino] acridine and method for its production |
| US2718487A (en) * | 1950-12-18 | 1955-09-20 | Hoechst Ag | Hemostatics containing reaction products of thrombin and acridines and process of preparing same |
| US3019227A (en) * | 1960-01-07 | 1962-01-30 | Houdry Process Corp | Alkyl acridines |
| US3067137A (en) * | 1959-04-29 | 1962-12-04 | Shell Oil Co | Lubricant compositions containing 9-amino acridines |
| US3122553A (en) * | 1959-08-20 | 1964-02-25 | Bansen Inc | 4-alkyl resorcinolates of aminoacridines |
| US3149068A (en) * | 1961-03-08 | 1964-09-15 | Cities Service Res & Dev Co | Geochemical exploration |
-
1964
- 1964-01-23 US US339608A patent/US3279068A/en not_active Expired - Lifetime
Patent Citations (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US1766403A (en) * | 1930-06-24 | Weener schtjlemann | ||
| US2092131A (en) * | 1937-09-07 | S-of amino ackibines | ||
| US1629873A (en) * | 1919-07-08 | 1927-05-24 | Ig Farbenindustrie Ag | Acridine derivatives and process of making same |
| US1889704A (en) * | 1925-12-24 | 1932-11-29 | Winthrop Chem Co Inc | Compounds of the acridine series and process of making them |
| US1760781A (en) * | 1926-12-20 | 1930-05-27 | Winthrop Chem Co Inc | Manufacture of new pharmaceutical products |
| US2113357A (en) * | 1930-05-09 | 1938-04-05 | Winthrop Chem Co Inc | Basically substituted amino-acridine derivatives |
| US2121207A (en) * | 1934-06-07 | 1938-06-21 | Winthrop Chem Co Inc | New basically substituted acridine compounds |
| US2124590A (en) * | 1934-11-09 | 1938-07-26 | Du Pont | Dye finishing process |
| US2155501A (en) * | 1936-04-11 | 1939-04-25 | Agfa Ansco Corp | Photographic treating bath |
| US2151495A (en) * | 1937-04-05 | 1939-03-21 | David V Bender | Disclosing solution |
| US2334348A (en) * | 1941-06-23 | 1943-11-16 | Nat Marking Mach Co | Sunburn preventive |
| US2488904A (en) * | 1945-03-03 | 1949-11-22 | Sterling Drug Inc | 1-methyl-5-aminoacridine and process for preparing it |
| US2531010A (en) * | 1949-01-22 | 1950-11-21 | Sterling Drug Inc | 9-[2-(2-hydroxyethylamino) ethylamino] acridine and method for its production |
| US2718487A (en) * | 1950-12-18 | 1955-09-20 | Hoechst Ag | Hemostatics containing reaction products of thrombin and acridines and process of preparing same |
| US3067137A (en) * | 1959-04-29 | 1962-12-04 | Shell Oil Co | Lubricant compositions containing 9-amino acridines |
| US3122553A (en) * | 1959-08-20 | 1964-02-25 | Bansen Inc | 4-alkyl resorcinolates of aminoacridines |
| US3019227A (en) * | 1960-01-07 | 1962-01-30 | Houdry Process Corp | Alkyl acridines |
| US3149068A (en) * | 1961-03-08 | 1964-09-15 | Cities Service Res & Dev Co | Geochemical exploration |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3624219A (en) * | 1970-07-06 | 1971-11-30 | Max J Perlitsh | Plaque-disclosing composition and package system |
| US3903252A (en) * | 1972-06-08 | 1975-09-02 | Lorvic Corp | Dental disclosing compositions and the method of making and using the same |
| US4347233A (en) * | 1978-12-04 | 1982-08-31 | Kuraray Company, Limited | Dental caries detection |
| US4976951A (en) * | 1985-08-28 | 1990-12-11 | Melvyn Rosenberg | Dental caries diagnostic and localization technique |
| US5357989A (en) * | 1990-12-10 | 1994-10-25 | Naresh Gathani | Dental cleansing member |
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