DE1768759A1 - Tin salts of phosphonic acids - Google Patents
Tin salts of phosphonic acidsInfo
- Publication number
- DE1768759A1 DE1768759A1 DE19681768759 DE1768759A DE1768759A1 DE 1768759 A1 DE1768759 A1 DE 1768759A1 DE 19681768759 DE19681768759 DE 19681768759 DE 1768759 A DE1768759 A DE 1768759A DE 1768759 A1 DE1768759 A1 DE 1768759A1
- Authority
- DE
- Germany
- Prior art keywords
- fluoride
- tin
- group
- acid
- carbon atoms
- 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.)
- Pending
Links
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical class [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 title description 9
- 150000003009 phosphonic acids Chemical class 0.000 title description 3
- 239000002253 acid Substances 0.000 claims description 17
- -1 phenylethenyl Chemical group 0.000 claims description 13
- 239000000203 mixture Substances 0.000 claims description 11
- 125000004432 carbon atom Chemical group C* 0.000 claims description 9
- 125000000217 alkyl group Chemical group 0.000 claims description 7
- 230000015572 biosynthetic process Effects 0.000 claims description 7
- 208000002925 dental caries Diseases 0.000 claims description 7
- 229910052739 hydrogen Inorganic materials 0.000 claims description 7
- 239000001257 hydrogen Substances 0.000 claims description 7
- KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 claims description 6
- IUTCEZPPWBHGIX-UHFFFAOYSA-N tin(2+) Chemical class [Sn+2] IUTCEZPPWBHGIX-UHFFFAOYSA-N 0.000 claims description 6
- SXGRAKNNKBAFML-UHFFFAOYSA-N 1,3-diphosphonopropan-2-ylphosphonic acid Chemical compound OP(O)(=O)CC(P(O)(O)=O)CP(O)(O)=O SXGRAKNNKBAFML-UHFFFAOYSA-N 0.000 claims description 5
- 150000007513 acids Chemical class 0.000 claims description 5
- 125000003277 amino group Chemical group 0.000 claims description 4
- 150000002431 hydrogen Chemical group 0.000 claims description 4
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 4
- PUZPDOWCWNUUKD-UHFFFAOYSA-M sodium fluoride Chemical group [F-].[Na+] PUZPDOWCWNUUKD-UHFFFAOYSA-M 0.000 claims description 4
- 229910018828 PO3H2 Inorganic materials 0.000 claims description 3
- SLRMQYXOBQWXCR-UHFFFAOYSA-N 2154-56-5 Chemical compound [CH2]C1=CC=CC=C1 SLRMQYXOBQWXCR-UHFFFAOYSA-N 0.000 claims description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- 125000003342 alkenyl group Chemical group 0.000 claims description 2
- 125000003118 aryl group Chemical group 0.000 claims description 2
- CBOIHMRHGLHBPB-UHFFFAOYSA-N hydroxymethyl Chemical group O[CH2] CBOIHMRHGLHBPB-UHFFFAOYSA-N 0.000 claims description 2
- 235000013024 sodium fluoride Nutrition 0.000 claims description 2
- 239000011775 sodium fluoride Substances 0.000 claims description 2
- ANOBYBYXJXCGBS-UHFFFAOYSA-L stannous fluoride Chemical group F[Sn]F ANOBYBYXJXCGBS-UHFFFAOYSA-L 0.000 claims 1
- 229960002799 stannous fluoride Drugs 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 description 7
- SFRLSTJPMFGBDP-UHFFFAOYSA-N 1,2-diphosphonoethylphosphonic acid Chemical compound OP(O)(=O)CC(P(O)(O)=O)P(O)(O)=O SFRLSTJPMFGBDP-UHFFFAOYSA-N 0.000 description 4
- 208000006558 Dental Calculus Diseases 0.000 description 4
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 4
- 239000002324 mouth wash Substances 0.000 description 4
- 239000000606 toothpaste Substances 0.000 description 4
- ZWVMLYRJXORSEP-LURJTMIESA-N (2s)-hexane-1,2,6-triol Chemical compound OCCCC[C@H](O)CO ZWVMLYRJXORSEP-LURJTMIESA-N 0.000 description 3
- ABLZXFCXXLZCGV-UHFFFAOYSA-N Phosphorous acid Chemical compound OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- 229940051866 mouthwash Drugs 0.000 description 3
- 239000006072 paste Substances 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- 229940034610 toothpaste Drugs 0.000 description 3
- YVPHSTVRTGSOSK-UHFFFAOYSA-N 1,3,3-triphosphonopropylphosphonic acid Chemical compound OP(O)(=O)C(P(O)(O)=O)CC(P(O)(O)=O)P(O)(O)=O YVPHSTVRTGSOSK-UHFFFAOYSA-N 0.000 description 2
- RHWUIRMVPYNGIV-UHFFFAOYSA-N 1,3,4-triphosphonobutan-2-ylphosphonic acid Chemical compound OP(O)(=O)CC(P(O)(O)=O)C(P(O)(O)=O)CP(O)(O)=O RHWUIRMVPYNGIV-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- NVCBLOZVMWSNST-UHFFFAOYSA-N OP(=O)OP(O)=O.CNC1=CC=CC=C1 Chemical compound OP(=O)OP(O)=O.CNC1=CC=CC=C1 NVCBLOZVMWSNST-UHFFFAOYSA-N 0.000 description 2
- DPOPAJRDYZGTIR-UHFFFAOYSA-N Tetrazine Chemical compound C1=CN=NN=N1 DPOPAJRDYZGTIR-UHFFFAOYSA-N 0.000 description 2
- 229910021626 Tin(II) chloride Inorganic materials 0.000 description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 2
- 229940112822 chewing gum Drugs 0.000 description 2
- 235000015218 chewing gum Nutrition 0.000 description 2
- XQRLCLUYWUNEEH-UHFFFAOYSA-N diphosphonic acid Chemical compound OP(=O)OP(O)=O XQRLCLUYWUNEEH-UHFFFAOYSA-N 0.000 description 2
- 238000009472 formulation Methods 0.000 description 2
- 235000011187 glycerol Nutrition 0.000 description 2
- 229910052736 halogen Inorganic materials 0.000 description 2
- 150000002367 halogens Chemical group 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 235000011150 stannous chloride Nutrition 0.000 description 2
- AXZWODMDQAVCJE-UHFFFAOYSA-L tin(II) chloride (anhydrous) Chemical compound [Cl-].[Cl-].[Sn+2] AXZWODMDQAVCJE-UHFFFAOYSA-L 0.000 description 2
- JFZBZVINWPKXFH-UHFFFAOYSA-N 1,1,3-triphosphonopropylphosphonic acid Chemical compound C(CCP(O)(=O)O)(P(O)(=O)O)(P(O)(=O)O)P(O)(=O)O JFZBZVINWPKXFH-UHFFFAOYSA-N 0.000 description 1
- HPACKUSWEBMYJE-UHFFFAOYSA-N 1,2,3,5,6,7,8-heptaphosphonooctan-4-ylphosphonic acid Chemical compound OP(O)(=O)CC(P(O)(O)=O)C(P(O)(O)=O)C(P(O)(O)=O)C(P(O)(O)=O)C(P(O)(O)=O)C(P(O)(O)=O)CP(O)(O)=O HPACKUSWEBMYJE-UHFFFAOYSA-N 0.000 description 1
- XWFHTVUSIQXPJR-UHFFFAOYSA-N 1,2,3,5,6,7-hexaphosphonoheptan-4-ylphosphonic acid Chemical compound OP(O)(=O)CC(P(O)(O)=O)C(P(O)(O)=O)C(P(O)(O)=O)C(P(O)(O)=O)C(P(O)(O)=O)CP(O)(O)=O XWFHTVUSIQXPJR-UHFFFAOYSA-N 0.000 description 1
- CCSPRGDNSSMNIH-UHFFFAOYSA-N 1,2,4,5,6-pentaphosphonohexan-3-ylphosphonic acid Chemical compound OP(O)(=O)CC(P(O)(O)=O)C(P(O)(O)=O)C(P(O)(O)=O)C(P(O)(O)=O)CP(O)(O)=O CCSPRGDNSSMNIH-UHFFFAOYSA-N 0.000 description 1
- UWOPXOPPISBKGY-UHFFFAOYSA-N 1,2,4,5-tetraphosphonopentan-3-ylphosphonic acid Chemical compound OP(O)(=O)CC(P(O)(O)=O)C(P(O)(O)=O)C(P(O)(O)=O)CP(O)(O)=O UWOPXOPPISBKGY-UHFFFAOYSA-N 0.000 description 1
- DOEKKHHOJPCRQN-UHFFFAOYSA-N 1-phosphonotetradecylphosphonic acid Chemical compound CCCCCCCCCCCCCC(P(O)(O)=O)P(O)(O)=O DOEKKHHOJPCRQN-UHFFFAOYSA-N 0.000 description 1
- HRGUSFBJBOKSML-UHFFFAOYSA-N 3',5'-di-O-methyltricetin Chemical compound COC1=C(O)C(OC)=CC(C=2OC3=CC(O)=CC(O)=C3C(=O)C=2)=C1 HRGUSFBJBOKSML-UHFFFAOYSA-N 0.000 description 1
- VACXNTDDDOYUQP-UHFFFAOYSA-N 8-phosphonopentadecan-8-ylphosphonic acid Chemical compound CCCCCCCC(CCCCCCC)(P(O)(O)=O)P(O)(O)=O VACXNTDDDOYUQP-UHFFFAOYSA-N 0.000 description 1
- FOLKCBRADAKWQI-UHFFFAOYSA-N CNC(C)=O.OP(=O)OP(O)=O Chemical compound CNC(C)=O.OP(=O)OP(O)=O FOLKCBRADAKWQI-UHFFFAOYSA-N 0.000 description 1
- OZZNEHCWFMJHHS-UHFFFAOYSA-N CNCCO.OP(=O)OP(O)=O Chemical compound CNCCO.OP(=O)OP(O)=O OZZNEHCWFMJHHS-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- DAOANAATJZWTSJ-UHFFFAOYSA-N N-Decanoylmorpholine Chemical compound CCCCCCCCCC(=O)N1CCOCC1 DAOANAATJZWTSJ-UHFFFAOYSA-N 0.000 description 1
- IDDMFNIRSJVBHE-UHFFFAOYSA-N Piscigenin Natural products COC1=C(O)C(OC)=CC(C=2C(C3=C(O)C=C(O)C=C3OC=2)=O)=C1 IDDMFNIRSJVBHE-UHFFFAOYSA-N 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical compound [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 description 1
- 239000004141 Sodium laurylsulphate Substances 0.000 description 1
- BFDMEODWJJUORJ-UHFFFAOYSA-N [dimethylamino(phosphono)methyl]phosphonic acid Chemical compound CN(C)C(P(O)(O)=O)P(O)(O)=O BFDMEODWJJUORJ-UHFFFAOYSA-N 0.000 description 1
- DPXJVFZANSGRMM-UHFFFAOYSA-N acetic acid;2,3,4,5,6-pentahydroxyhexanal;sodium Chemical compound [Na].CC(O)=O.OCC(O)C(O)C(O)C(O)C=O DPXJVFZANSGRMM-UHFFFAOYSA-N 0.000 description 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- SNAAJJQQZSMGQD-UHFFFAOYSA-N aluminum magnesium Chemical compound [Mg].[Al] SNAAJJQQZSMGQD-UHFFFAOYSA-N 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- JUNWLZAGQLJVLR-UHFFFAOYSA-J calcium diphosphate Chemical compound [Ca+2].[Ca+2].[O-]P([O-])(=O)OP([O-])([O-])=O JUNWLZAGQLJVLR-UHFFFAOYSA-J 0.000 description 1
- 229940043256 calcium pyrophosphate Drugs 0.000 description 1
- 239000001768 carboxy methyl cellulose Substances 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000004927 clay Substances 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 239000003433 contraceptive agent Substances 0.000 description 1
- 230000002254 contraceptive effect Effects 0.000 description 1
- 125000000753 cycloalkyl group Chemical group 0.000 description 1
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
- 235000019821 dicalcium diphosphate Nutrition 0.000 description 1
- KCFYHBSOLOXZIF-UHFFFAOYSA-N dihydrochrysin Natural products COC1=C(O)C(OC)=CC(C2OC3=CC(O)=CC(O)=C3C(=O)C2)=C1 KCFYHBSOLOXZIF-UHFFFAOYSA-N 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 239000000796 flavoring agent Substances 0.000 description 1
- 235000019634 flavors Nutrition 0.000 description 1
- 150000002222 fluorine compounds Chemical class 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- YRBKSJIXFZPPGF-UHFFFAOYSA-N hexazine Chemical compound N1=NN=NN=N1 YRBKSJIXFZPPGF-UHFFFAOYSA-N 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000002304 perfume Substances 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- UEZVMMHDMIWARA-UHFFFAOYSA-M phosphonate Chemical compound [O-]P(=O)=O UEZVMMHDMIWARA-UHFFFAOYSA-M 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 230000000069 prophylactic effect Effects 0.000 description 1
- 238000011321 prophylaxis Methods 0.000 description 1
- 150000003254 radicals Chemical group 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- 230000000979 retarding effect Effects 0.000 description 1
- CVHZOJJKTDOEJC-UHFFFAOYSA-N saccharin Chemical compound C1=CC=C2C(=O)NS(=O)(=O)C2=C1 CVHZOJJKTDOEJC-UHFFFAOYSA-N 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 235000019812 sodium carboxymethyl cellulose Nutrition 0.000 description 1
- 229920001027 sodium carboxymethylcellulose Polymers 0.000 description 1
- 235000019333 sodium laurylsulphate Nutrition 0.000 description 1
- 230000000699 topical effect Effects 0.000 description 1
- BMCJATLPEJCACU-UHFFFAOYSA-N tricin Natural products COc1cc(OC)c(O)c(c1)C2=CC(=O)c3c(O)cc(O)cc3O2 BMCJATLPEJCACU-UHFFFAOYSA-N 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/38—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)]
- C07F9/3804—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)] not used, see subgroups
- C07F9/3839—Polyphosphonic acids
-
- 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
- A61K8/55—Phosphorus compounds
-
- 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
Landscapes
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Organic Chemistry (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Molecular Biology (AREA)
- Birds (AREA)
- Epidemiology (AREA)
- Biochemistry (AREA)
- Oral & Maxillofacial Surgery (AREA)
- Cosmetics (AREA)
Description
Zinnsalze von Phosphonsäuren. Tin salts of phosphonic acids.
Im Hauptpatent (Patentanmeldung P 43 625 IVb/12 o) werden neue Di-zinn(II)-gem-diphosphonate sowie orale Zusammensetzungen zur Verhütung von Karies und Zahnsteinbildung, die diese Zinnsalze enthalten, offenbart. Es handelt sioh dort um die Di-Zinn(II)-salze von Phosphonsäuren der Formel in der R1 Wasserstoff, Halogen, Hydroxyl, Benzyl oder einen Alkyl-, Hydroxyalkyl-, Methoxyalkyl- oder Carboxyalkylrest mit 1 biß 12 C-Atomen, und R2 Wasserstoff, Halogen, Hydroxyl, Acetyl, Phenyl, Benzyl oder einen Alkyl-, Hydroxyalkyl-, Methoxyalkyl-oder Carboxyalkylrest mit 1 bia 12 C-Atomen bedeuten.The main patent (patent application P 43 625 IVb / 12 o) discloses new di-tin (II) gem-diphosphonates and oral compositions for preventing tooth decay and tartar formation which contain these tin salts. It is there about the di-tin (II) salts of phosphonic acids of the formula in which R1 is hydrogen, halogen, hydroxyl, benzyl or an alkyl, hydroxyalkyl, methoxyalkyl or carboxyalkyl radical with 1 to 12 carbon atoms, and R2 is hydrogen, halogen, hydroxyl, acetyl, phenyl, benzyl or an alkyl, hydroxyalkyl , Methoxyalkyl or carboxyalkyl radical with 1 to 12 carbon atoms.
Ferner werden im Hauptpatent Mundpflegemittel in Form von Zahnpasten, Mundwässern, Kaugummis, Prophylaxe-pasten, örtlich anwendbaren Lösungen und dgl. beschrieben, die (1) ein wasserlösliches Fluorid in einer zur Bereitstellung von etwa 100 bis 4000 ppm Fluoridionen ausreichenden Menge, und (2) etwa 0t05 bis 5,0 Gew.% des Di-zinn(II)-salzes der obigen gem-Diphosphonsäure enthalten, wobei der pH-Wert der Zusammensetzung zwischen etwa 2,5 und 7 liegt0 Es wurden nun weitere neue Zinn(II)-polyphosphonate gefunden, die bei Verwendung in oralen Zusammensetzungen bezw. Furthermore, the main patent includes oral care products in the form of toothpastes, Mouthwashes, chewing gum, prophylactic pastes, topical solutions and the like. described that (1) a water-soluble fluoride in a to provide about 100 to 4000 ppm fluoride ions sufficient; and (2) about 0t05 to 5.0 % By weight of the di-tin (II) salt of the above gem-diphosphonic acid, the The pH of the composition is between about 2.5 and 7 0 There have now been more new stannous polyphosphonates found when used in oral compositions respectively
Mundpflegemitteln beständig gegen Hydrolyse und Umwandlung in inaktive Formen sind. Diese neuen Salse besitzen ebenfalls, wie die Verbindungen des Hauptpatents, eine die Karies- und Zahneteinbildung verhütende Wirkung Die neuen Zinn (II)-polyphosphonate besitzen die Formeln n in denen R1 und R2 Wasserstoff oder die CH2OH-Gruppe, eine ganze Zahl von 2 bis 10, R3 eine Phenyläthenyl-, eine Aminogruppe, eine substituierte Aminogruppe (z.3. Dimethylamino, Diäthylamino, N-Hydroxy-N-äthylamino, Aoetylamino), -CH2PO3H2' -CH(PO3H2)(OH), - CH2CH(PO3H2)2, -CH2CH2PO3H2, eine Cycloalkylgruppe (z.B. Cyclopropyl, Cyclobutyl, Cyclopentyl, Cyclohexyl), eine Alkylgruppe mit 13 bis 20 C-Atomen, oder eine Alkenylgruppe mit 2 bis 20 C-Atomen, und R4 Wasserstoff, Amino, Hydroxyl, -CH2PO3H2, einen Aryl- oder Benzylrest oder einen Alkyl-, Hydroxyalkyl-, Methoxyalkyl- oder Carboxyalkylrest mit 1 bis 12 C-Atomen darstellen.Oral care products are resistant to hydrolysis and conversion to inactive forms. Like the compounds of the main patent, these new Salse also have an effect that prevents tooth decay and the formation of teeth. The new tin (II) polyphosphonates have the formulas n in which R1 and R2 are hydrogen or the CH2OH group, an integer from 2 to 10, R3 is a phenylethenyl, an amino group, a substituted amino group (e.g. dimethylamino, diethylamino, N-hydroxy-N-ethylamino, aoetylamino ), -CH2PO3H2 '-CH (PO3H2) (OH), - CH2CH (PO3H2) 2, -CH2CH2PO3H2, a cycloalkyl group (e.g. cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl), an alkyl group with 13 to 20 carbon atoms, or an alkenyl group with 2 to 20 carbon atoms, and R4 represent hydrogen, amino, hydroxyl, -CH2PO3H2, an aryl or benzyl radical or an alkyl, hydroxyalkyl, methoxyalkyl or carboxyalkyl radical with 1 to 12 carbon atoms.
Zu den Polyphosphonsäuren der Formel I, aus denen man die entsprechenden erfindungsgemä#en Zinn(II)-vic. Polyphosphonate heratellen kann, gehören z.B. Propan-1,2,3-triphosphonsäure, Butan-1,2,3,4-tetraphosphonsäure, Hexan-1,2,3,4,-5,6,-hexaphosphonsäure, Hexan-1-hydroxy-2,3,4,5,6-pentaphosphonsäure, Hexan-1,6-dihydroxy-2,3,4,5,-tetraphosphonsäure, Pentan-1,2,3,4,5,-pentaphosphonsäure, Heptan-1,2,3,4,5,6,7-heptaphosphonsäure, Octan-1,2,3,4,5,6,7,8-octaphosphonsaure, Nonan-1,2,3,4,5,6,7,8,9-nonophosphonsäure. The polyphosphonic acids of the formula I, from which one can use the appropriate tin (II) vic. Polyphosphonates can be produced, include e.g. propane-1,2,3-triphosphonic acid, Butane-1,2,3,4-tetraphosphonic acid, hexane-1,2,3,4, -5,6, -hexaphosphonic acid, hexane-1-hydroxy-2,3,4,5,6-pentaphosphonic acid, Hexane-1,6-dihydroxy-2,3,4,5-tetraphosphonic acid, pentane-1,2,3,4,5-pentaphosphonic acid, Heptane-1,2,3,4,5,6,7-heptaphosphonic acid, octane-1,2,3,4,5,6,7,8-octaphosphonic acid, Nonane-1,2,3,4,5,6,7,8,9-nonophosphonic acid.
Propan-1, 2, 3-triphosphonsäure, Butan-1,2,3,4-tetraphosphonsäureund die obengenannten höheren aliphatischen vic.-Polyphosphonsäuren können erhalten werden, indem man eine Alkinverbindung der Formel R-(C#C)m-CH2 X, in der R Wasserstoff oder einen Rest -CH2X, X ein Halogenatom oder eine Hydroxylgruppe, und m eine ganze Zahl von 1 bis 4 bedeutet, mit einem Dialkylphosphit, deseen Alkylgruppen 1 - 6 C-Atome enthalten, in Gegenwart von Natrium, Kalium, Lithium oder deren Mydriden umsetzt, und den so erhaltonen Ester in an sich bekannter Weise in die entsprechende Säure überführt.Propane-1, 2, 3-triphosphonic acid, butane-1,2,3,4-tetraphosphonic acid and the above-mentioned higher aliphatic vic. polyphosphonic acids can be obtained by adding an alkyne compound of the formula R- (C # C) m-CH2 X, in which R is hydrogen or a radical -CH2X, X is a halogen atom or a hydroxyl group, and m is a whole Number from 1 to 4 means, with a dialkyl phosphite, deseen alkyl groups 1 - 6 Containing carbon atoms in the presence of sodium, potassium, lithium or their mydrids converts, and the ester thus obtained in a manner known per se in the corresponding Acid transferred.
Die Polyphos-phonsäuren der Formel II, aus denen di erfindungsgemä#en Zinn(II)-gem-polyphosphonate hergtellbar sind, umfassen z. B. Äthan-1,1,2-triphosphonsäure, Propan-1, t 3,3-tetraphosphonsäure, Äthan-i-amino-1, 1-diphosphonsäure, Propan-1-hydroxy-1,1,3-triphosphonsäure, Äthan-2-hydroxy-1, 1;2-triphosphonsäure, Methancyclohexylhydroxy diphosphonsäure, Tetradecan-1,1-diphosphonsäure, Pent-4-en-1-hydroxy-1,1-diphosphonsäure, Octadec-9-enl-hydroxy-i' 1-diphosphonsäure, 3-Phenyl-1,1,1-diphosphonoäure-prop-2-en, Phenylaininomethan diphosphonsäure, Naphthylaminomethan-diphosphonsäure, N,N-Dimethylaminomethan-diphosphonsäure, N-(2-Hydroxyäthyl)-aminomethan-diphosphonsäure, N-Acetylaminomethan-diphosphonsäure, Aminomethandiphesphonsäure.The polyphosphonic acids of the formula II, from which they according to the invention Tin (II) gem polyphosphonates are hergtellbar, include e.g. B. ethane-1,1,2-triphosphonic acid, Propane-1, t 3,3-tetraphosphonic acid, ethane-i-amino-1, 1-diphosphonic acid, propane-1-hydroxy-1,1,3-triphosphonic acid, Ethane-2-hydroxy-1,1; 2-triphosphonic acid, methanecyclohexylhydroxy diphosphonic acid, Tetradecane-1,1-diphosphonic acid, pent-4-en-1-hydroxy-1,1-diphosphonic acid, octadec-9-enl-hydroxy-i ' 1-diphosphonic acid, 3-phenyl-1,1,1-diphosphonoic acid-prop-2-en, phenylaminomethane diphosphonic acid, naphthylaminomethane diphosphonic acid, N, N-dimethylaminomethane diphosphonic acid, N- (2-hydroxyethyl) aminomethane diphosphonic acid, N-acetylaminomethane diphosphonic acid, Aminomethanediphesphonic acid.
Äthan-1,1,2-triphosphonsäure und verwandte Verbindungen der Formel II können nach dem in Journ. Chem. Soc. [London] Juni 1963, S. 3351 - 3360 beschriebenen Verfahren hergestellt werden. Ethane-1,1,2-triphosphonic acid and related compounds of the formula II can after the in Journ. Chem. Soc. [London] June 1963, pp. 3351-3360 Process are produced.
Propan-1,1,3,3-tetraphosphonsäure und ähnliche Verbindungen können hergestellt werden, in-dem man ein Alkalimetall-carbanion eines Tetraalkylmethylendiphosphcnats mit einem Dihalogenmethan in Gegenwart eines organischen Losungsmittels umsetzt. Propane-1,1,3,3-tetraphosphonic acid and similar compounds can be prepared in-by adding an alkali metal carbanion of a Tetraalkylmethylendiphosphcnats with a dihalomethane in the presence of an organic solvent.
Weitere Verbindungen der Formel II können nach den im Stammpatent angegebenen Verfahren erhalten werden0 Die Zinn(II)-salze der obigen Polyphosphonsäuren werden nach den Verfahren von Beispiel I des Hauptpatents (Patentanmeldung P 43 625 IVb/120) hergestellt, indem man eine wässrig. Lösung der entsprechenden Saure mit SnCl2 umsetzt. Im vorliegenden Fall wird eine zur Bereitstellung eines Molverhältnisses von zweiwertigem Zinn zu Polyphosphonsäure von 2:1 bts 10:1 - je nach der Anzahl der Phosphonsauregruppen in der Verbindung - ausreichende Menge an SnCl2 eingesetzt. Vorzugsweise arbeitet man mit 1 Mol zweiwertigem Zinn pro Phosphonsauregruppe. Further compounds of the formula II can according to the parent patent The stannous salts of the above polyphosphonic acids are obtained are carried out according to the procedure of example I of the main patent (patent application P 43 625 IVb / 120) prepared by using an aqueous. Solution of the corresponding acid with SnCl2. In the present case, one is used to provide a molar ratio from divalent tin to polyphosphonic acid from 2: 1 to 10: 1 - depending on the number of the phosphonic acid groups in the compound - sufficient amount of SnCl2 used. It is preferred to work with 1 mol of divalent tin per phosphonic acid group.
Ein bevorzugtes Zinn(II)-polyphosphonat gemaß vorliegender Erfindung ist Trizinn(II)-propan-1,2,3-triphosphonat. A preferred stannous polyphosphonate according to the present invention is trizinn (II) propane-1,2,3-triphosphonate.
Die erfindungsgemä#en oralen Zusammensetzungen zur Kariesprophylaxe und Verhütung von Zahnsteinbildung enthalten (1) ein wasserlösliches Fluorid in einer zur Bereitstellung von etwa 100 bis 4000 ppm Fluoridionen ausreichenden Mengen, und (2) etwa 0,05 bis 5,0 Gew.% eines Zinn(II)-phosphonats der vorstehend beschriebenen Art, wobei der pH-Wert der Gemische zwischen etwa 2,5 und 7,0 liegt. weitere Einzelheiten, wie Beispiele fur verwendbare Fluoride, Beschreibung der Zahnpastenbestandteile, bevorzugte Konzentratiansn der einzelnen Komponenten sind dem Hauptpatent zu entnehmen. The oral compositions according to the invention for caries prophylaxis and preventing tartar formation contain (1) a water-soluble fluoride in an amount sufficient to provide about 100 to 4000 ppm of fluoride ions, and (2) about 0.05 to 5.0 weight percent of a stannous phosphonate of those described above Kind, the pH of the mixtures being between about 2.5 and 7.0. more details, such as examples of fluorides that can be used, description of the toothpaste components, preferred concentrates of the individual components can be found in the main patent.
Beispiel 1 In üblicher Weise wird eine Zahnpaste folgender Zusammensetzung hergestellt: Gew.-% Calciumpyrophosphat 37,80 wassrige Lösung Serbitol (30% ####### ########) 19,38 Glycerin 9,69 Natrium-carboxyme thylcellulose 1,02 Magnesium-aluminium-silicat 0,39 Natrium-laurylsulfat 2,35 Ja-Sacoharin 0,14 Aroma und Parbstoff 1,45 Zinn(II)-fluorid 0,39 Tri-Zinn(II)-äthan-1,1,2-triphosphonat 0,48 Wasser Rest pH : 6,2 Beim Test nach der im Hauptpatent beschriebenen Methode zeigte siah, daß die Zahnpaste gemäß obiges Beispiel gegenüber einer Vergleichspaste mit äquivalenter Zinn(II)-konzentration, Jedoch ohne das Trizinn(II)-äthan-1,1,2-triphosphonat, wesentlich iehr zur Verfügung stehendes Zinn aufweist. Bei normaler Anwendung verhindert diese Paste die Bildung v@. Karies und Zahnstein auch nach längerer Lagerzeit noch, Im wesentlichen analoge Ergebnisse wurden erzielt, wenn azwtelle Ton Trizinn(II)-äthan-1,1,2-triphosphonat mit Trizinn (II)-propan-1,2,3-triphosphonat, Tetrazinn(II)-butan-1,2,3,4-tetraphosphonat, Hexazinn(II)-hexan-1,2,3,4,5,6-hexaphosphonat oder Tetrazinn(II)-hexan-1,6-dihydroxy-2,3,4,5,-tetraphosphonat gearbeitet wurde.Example 1 In the usual way, a toothpaste of the following composition manufactured: wt .-% calcium pyrophosphate 37.80 aqueous solution Serbitol (30% ####### ########) 19.38 glycerine 9.69 sodium carboxymethyl cellulose 1.02 magnesium aluminum silicate 0.39 Sodium Lauryl Sulphate 2.35 Yes-Sacoharine 0.14 Flavor and Perfume 1.45 Tin (II) Fluoride 0.39 tri-tin (II) -ethane-1,1,2-triphosphonate 0.48 water balance pH: 6.2 during the test using the method described in the main patent, siah showed that the toothpaste according to The above example compared to a comparative paste with an equivalent tin (II) concentration, However, without the trizinn (II) ethane-1,1,2-triphosphonate, it is essentially available has standing tin. With normal use, this paste prevents the formation v @. Tooth decay and tartar, even after a long period of storage, are essentially the same Results were obtained when azwtelle clay was tricin (II) ethane-1,1,2-triphosphonate with trizinn (II) propane-1,2,3-triphosphonate, tetrazinn (II) -butane-1,2,3,4-tetraphosphonate, Hexazine (II) hexane-1,2,3,4,5,6-hexaphosphonate or tetrazine (II) hexane-1,6-dihydroxy-2,3,4,5-tetraphosphonate was worked.
Beispiel 2 In üblicher Weise wird ein Mundwasser folgender Zusammen-Setzung hergestellt: Gew.-% Äthanol (50%) 83,00 Glycerin 13>76 Aroma 0,85 Saccharin 0,12 Natrium-fluorid 0,27 Tetra-Zinn(II)-propan-1,1,3,3-tetraphosphonat 2,00 pH X 6,5 Bei normaler Anwendung stellt das obige Mundwasser ein wirksames Verhütungsmittel gegen Karies und Zahnsteinbildung dar. Ein hoher Gehalt an verfügbarem zweiwertiger Zinn wird während der gesamten Lagerzeit des Produktes aufrecht erhaltenO Analoge Ergebnisse erhält man mit Mundwasser mit einer Formulierung gemäß Beispiel 2, die jedoch anstelle des Tetrazinn(II )-propan-l ,1,3, 3-tetraphosphonats eine der folgenden Verbindungen in einer die äquivalente Zinn(II)-menge liefernden Konzentration enthalten: Mzinn(II)-Bthan-l-amino-),l-diphosphonat, Trizinn(II ) -propan-1-hydroxy-1 ,1 ,3-triphosphonat, Trizinn(II)-äthan-2-hydroxy-1,1,2-triphosphonat, Dizinn(II)-methan-cylohexylhydroxydiphosphonat, Dizinn(II )-heiadecan-l , 1-diphosphonat, Dizinn(II)-o @@@-9-en-1-hydroxy-1,1-diphosphonat, Dizinn(II)-3-phenyl-1,1-diphosphonoprop-2-en.Example 2 In the usual way, a mouthwash of the following composition is made manufactured: % By weight ethanol (50%) 83.00 glycerine 13> 76 aroma 0.85 saccharine 0.12 sodium fluoride 0.27 tetra-tin (II) propane-1,1,3,3-tetraphosphonate 2.00 pH X 6.5 With normal use, the above mouthwash is an effective contraceptive against tooth decay and tartar formation. A high content of available divalent Tin is retained throughout the product's shelf lifeO Analogs Results are obtained with mouthwash with a formulation according to Example 2, the but instead of the tetrazine (II) propane-1,3,3,3-tetraphosphonate one of the following Contain compounds in a concentration that provides the equivalent amount of tin (II): Mtin (II) -thane-l-amino -), l-diphosphonate, trin (II) propane-1-hydroxy-1, 1, 3-triphosphonate, Trizinn (II) ethane-2-hydroxy-1,1,2-triphosphonate, ditin (II) -methane-cyclohexylhydroxydiphosphonat, Dizinn (II) -heiadecan-l, 1-diphosphonat, Dizinn (II) -o @@@ - 9-en-1-hydroxy-1,1-diphosphonate, Ditin (II) -3-phenyl-1,1-diphosphonoprop-2-ene.
Beispiel 3 Kaugummi-Grundmassen werden nach der Formulierung von Beispiel 23 des Hauptpatents (Anm.Nr. P 43 625 IVb/12 o) hergestellt, wobei das Dizinn(II)-pentadecan-8,8-diphosphonat durch eine der folgenden Verbindungen ersetzt wird: Dizinn(II)-phenylaminomethan-diphosphonat, Dizinn(II)-N,N-dimethylaminomethandiphosphonat t Dizinn(II)-N-(2-hydroxyäthyl)-aminomethan-diphosphonat, Dizinn(II)-N-acetylaminomethan-diphosphonat, Dizinn(II)-alinome than-diphosphonat.Example 3 Chewing gum bases are made according to the formulation of Example 23 of the main patent (note number P 43 625 IVb / 12 o), whereby the ditin (II) pentadecane-8,8-diphosphonate is replaced by one of the following compounds: ditin (II) phenylaminomethane diphosphonate, Dizinn (II) -N, N-dimethylaminomethanediphosphonate t Dizinn (II) -N- (2-hydroxyethyl) -aminomethane-diphosphonate, Dizinn (II) -N-acetylaminomethane-diphosphonate, Dizinn (II) -alinomethane-diphosphonat.
Diese Zusammensetzungen verzögern wirksam die Bildung von Karies und ZahnsteinD Der Gehalt an verfügbarem zweiwertigen Zinn bleibt über längere Zeiträume konstant. These compositions are effective in retarding tooth decay formation and tartarD The available divalent tin content remains for long periods of time constant.
Claims (5)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19681768759 DE1768759A1 (en) | 1968-06-27 | 1968-06-27 | Tin salts of phosphonic acids |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19681768759 DE1768759A1 (en) | 1968-06-27 | 1968-06-27 | Tin salts of phosphonic acids |
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| Publication Number | Publication Date |
|---|---|
| DE1768759A1 true DE1768759A1 (en) | 1972-01-13 |
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19681768759 Pending DE1768759A1 (en) | 1968-06-27 | 1968-06-27 | Tin salts of phosphonic acids |
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| DE (1) | DE1768759A1 (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0000061A1 (en) * | 1977-06-14 | 1978-12-20 | Hoechst Aktiengesellschaft | Derivatives of carboxylic acid that contain phosphorus, process for their preparation and their utilisation |
| WO1995008979A1 (en) * | 1993-09-29 | 1995-04-06 | The Procter & Gamble Company | Diphosphonic acid esters as tartar control agents |
-
1968
- 1968-06-27 DE DE19681768759 patent/DE1768759A1/en active Pending
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0000061A1 (en) * | 1977-06-14 | 1978-12-20 | Hoechst Aktiengesellschaft | Derivatives of carboxylic acid that contain phosphorus, process for their preparation and their utilisation |
| WO1995008979A1 (en) * | 1993-09-29 | 1995-04-06 | The Procter & Gamble Company | Diphosphonic acid esters as tartar control agents |
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