CH615097A5 - - Google Patents

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Publication number: CH615097A5
Authority: CH; Switzerland
Prior art keywords: salts; diphosphono; water; sodium; azacycloalkane
Prior art date: 1973-08-27

Application number

CH52779A

Other languages

English (en)

Inventor

Walter Dr Ploeger

Manfred Dr Schmidt-Dunker

Christian Dr Gloxhuber

Original Assignee

Henkel Kgaa

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.)

1973-08-27

Filing date

1979-01-18

Publication date

1980-01-15

1979-01-18 Application filed by Henkel Kgaa filed Critical Henkel Kgaa

1980-01-15 Publication of CH615097A5 publication Critical patent/CH615097A5/de

Links

150000003839 salts Chemical class 0.000 description 11
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 6
239000000203 mixture Substances 0.000 description 6
235000003599 food sweetener Nutrition 0.000 description 4
238000009472 formulation Methods 0.000 description 4
239000003765 sweetening agent Substances 0.000 description 4
239000000341 volatile oil Substances 0.000 description 4
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
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 3
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
239000002253 acid Substances 0.000 description 3
150000007513 acids Chemical class 0.000 description 3
230000015572 biosynthetic process Effects 0.000 description 3
125000004432 carbon atom Chemical group C* 0.000 description 3
235000011187 glycerol Nutrition 0.000 description 3
125000004435 hydrogen atom Chemical group [H]* 0.000 description 3
229910052708 sodium Inorganic materials 0.000 description 3
239000011734 sodium Substances 0.000 description 3
KFZXVMNBUMVKLN-UHFFFAOYSA-N 4-chloro-5-methyl-2-propan-2-ylphenol Chemical compound CC(C)C1=CC(Cl)=C(C)C=C1O KFZXVMNBUMVKLN-UHFFFAOYSA-N 0.000 description 2
208000006558 Dental Calculus Diseases 0.000 description 2
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 2
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 2
DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical compound [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 description 2
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 2
125000000217 alkyl group Chemical group 0.000 description 2
WNROFYMDJYEPJX-UHFFFAOYSA-K aluminium hydroxide Chemical compound [OH-].[OH-].[OH-].[Al+3] WNROFYMDJYEPJX-UHFFFAOYSA-K 0.000 description 2
150000003863 ammonium salts Chemical class 0.000 description 2
230000002421 anti-septic effect Effects 0.000 description 2
239000001768 carboxy methyl cellulose Substances 0.000 description 2
229940031956 chlorothymol Drugs 0.000 description 2
XQRLCLUYWUNEEH-UHFFFAOYSA-N diphosphonic acid Chemical compound OP(=O)OP(O)=O XQRLCLUYWUNEEH-UHFFFAOYSA-N 0.000 description 2
150000003951 lactams Chemical class 0.000 description 2
-1 mono- Chemical class 0.000 description 2
239000002324 mouth wash Substances 0.000 description 2
229910052698 phosphorus Inorganic materials 0.000 description 2
239000011574 phosphorus Substances 0.000 description 2
150000003018 phosphorus compounds Chemical class 0.000 description 2
229910052700 potassium Inorganic materials 0.000 description 2
239000011591 potassium Substances 0.000 description 2
239000000047 product Substances 0.000 description 2
229910002028 silica xerogel Inorganic materials 0.000 description 2
235000019812 sodium carboxymethyl cellulose Nutrition 0.000 description 2
229920001027 sodium carboxymethylcellulose Polymers 0.000 description 2
235000019333 sodium laurylsulphate Nutrition 0.000 description 2
239000000606 toothpaste Substances 0.000 description 2
ZLWCUTWVMUKDLJ-UHFFFAOYSA-N (2-phosphonopiperidin-2-yl)phosphonic acid Chemical compound OP(O)(=O)C1(P(O)(O)=O)CCCCN1 ZLWCUTWVMUKDLJ-UHFFFAOYSA-N 0.000 description 1
GDRWQOJIKFWLOC-UHFFFAOYSA-N (2-phosphonopyrrolidin-2-yl)phosphonic acid Chemical compound OP(O)(=O)C1(P(O)(O)=O)CCCN1 GDRWQOJIKFWLOC-UHFFFAOYSA-N 0.000 description 1
QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
208000002064 Dental Plaque Diseases 0.000 description 1
WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 1
QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
230000002378 acidificating effect Effects 0.000 description 1
239000003513 alkali Substances 0.000 description 1
HUMHYXGDUOGHTG-HEZXSMHISA-N alpha-D-GalpNAc-(1->3)-[alpha-L-Fucp-(1->2)]-D-Galp Chemical compound O[C@H]1[C@H](O)[C@H](O)[C@H](C)O[C@H]1O[C@@H]1[C@@H](O[C@@H]2[C@@H]([C@@H](O)[C@@H](O)[C@@H](CO)O2)NC(C)=O)[C@@H](O)[C@@H](CO)OC1O HUMHYXGDUOGHTG-HEZXSMHISA-N 0.000 description 1
229940064004 antiseptic throat preparations Drugs 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
239000002585 base Substances 0.000 description 1
150000001768 cations Chemical class 0.000 description 1
239000001913 cellulose Substances 0.000 description 1
229920002678 cellulose Polymers 0.000 description 1
238000006243 chemical reaction Methods 0.000 description 1
239000007795 chemical reaction product Substances 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
150000001875 compounds Chemical class 0.000 description 1
239000000470 constituent Substances 0.000 description 1
235000019441 ethanol Nutrition 0.000 description 1
229910021485 fumed silica Inorganic materials 0.000 description 1
210000002837 heart atrium Anatomy 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
238000004519 manufacturing process Methods 0.000 description 1
230000007935 neutral effect Effects 0.000 description 1
238000006386 neutralization reaction Methods 0.000 description 1
150000003009 phosphonic acids Chemical class 0.000 description 1
239000002510 pyrogen Substances 0.000 description 1
239000011541 reaction mixture Substances 0.000 description 1
239000000377 silicon dioxide Substances 0.000 description 1
MFSDELSXOVOZBJ-UHFFFAOYSA-M sodium;dodecyl sulfate;propane-1,2,3-triol Chemical compound [Na+].OCC(O)CO.CCCCCCCCCCCCOS([O-])(=O)=O MFSDELSXOVOZBJ-UHFFFAOYSA-M 0.000 description 1
239000000243 solution Substances 0.000 description 1
ISIJQEHRDSCQIU-UHFFFAOYSA-N tert-butyl 2,7-diazaspiro[4.5]decane-7-carboxylate Chemical compound C1N(C(=O)OC(C)(C)C)CCCC11CNCC1 ISIJQEHRDSCQIU-UHFFFAOYSA-N 0.000 description 1
239000002562 thickening agent Substances 0.000 description 1
GSEJCLTVZPLZKY-UHFFFAOYSA-O triethanolammonium Chemical class OCC[NH+](CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-O 0.000 description 1
239000000080 wetting agent Substances 0.000 description 1

Classifications

- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/66—Phosphorus compounds
- A61K31/675—Phosphorus compounds having nitrogen as a ring hetero atom, e.g. pyridoxal phosphate
- 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
- C—CHEMISTRY; METALLURGY
- C02—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
- C02F—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
- C02F5/00—Softening water; Preventing scale; Adding scale preventatives or scale removers to water, e.g. adding sequestering agents
- C02F5/08—Treatment of water with complexing chemicals or other solubilising agents for softening, scale prevention or scale removal, e.g. adding sequestering agents
- C02F5/10—Treatment of water with complexing chemicals or other solubilising agents for softening, scale prevention or scale removal, e.g. adding sequestering agents using organic substances
- C02F5/14—Treatment of water with complexing chemicals or other solubilising agents for softening, scale prevention or scale removal, e.g. adding sequestering agents using organic substances containing phosphorus
- 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
- C07F9/3873—Polyphosphonic acids containing nitrogen substituent, e.g. N.....H or N-hydrocarbon group which can be substituted by halogen or nitro(so), N.....O, N.....S, N.....C(=X)- (X =O, S), N.....N, N...C(=X)...N (X =O, S)
- 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
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/553—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having one nitrogen atom as the only ring hetero atom
- C07F9/5532—Seven-(or more) membered rings
- 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
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/553—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having one nitrogen atom as the only ring hetero atom
- C07F9/572—Five-membered rings

Landscapes

Chemical & Material Sciences (AREA)
Health & Medical Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
Organic Chemistry (AREA)
General Health & Medical Sciences (AREA)
Animal Behavior & Ethology (AREA)
Molecular Biology (AREA)
Biochemistry (AREA)
Veterinary Medicine (AREA)
Public Health (AREA)
Epidemiology (AREA)
Environmental & Geological Engineering (AREA)
Pharmacology & Pharmacy (AREA)
Water Supply & Treatment (AREA)
Engineering & Computer Science (AREA)
Hydrology & Water Resources (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Oral & Maxillofacial Surgery (AREA)
Chemical Kinetics & Catalysis (AREA)
Birds (AREA)
Cosmetics (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Detergent Compositions (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Compounds Of Alkaline-Earth Elements, Aluminum Or Rare-Earth Metals (AREA)

Description

615 097

2

PATENTANSPRUCH Mund- und Zahnpflegemittel, gekennzeichnet durch einen Gehalt an Diphosphonsäure der Formel

R

oder deren wasserlösliche Salze, wobei n 3-5 und R ein Wasserstoffatom oder eine Alkylgruppe mit 1-3 C-Atomen bedeuten.

Gegenstand der Erfindung sind Mund- und Zahnpflegemittel, die einen Gehalt an Diphosphonsäure der Formel

PO

oder deren wasserlösliche Salze, wobei n 3—5 und R ein Wasserstoffatom oder eine Alkylgruppe mit 1—3 C-Atomen bedeuten, aufweisen.

Es wurde gefunden, dass man mit derartigen Mitteln die Bildung von Zahnstein vermeiden kann. Zur Zahnsteinverhinderung können ausser den vorliegenden Phosphonsäuren auch die pharmakologisch unbedenklichen Salze wie Natrium-, Kalium-, Ammonium- und substituierten Ammoniumsalze wie Mono-, Di- oder Triäthanolammoniumsalze Verwendung finden. Sowohl die partiellen Salze, in denen nur ein Teil der aciden Protonen durch andere Kationen ersetzt ist, als auch die Vollsalze können benutzt werden.

Vorzuziehen sind jedoch solche Salze, die in wässriger Lösung annähernd neutral (pH 5—9) reagieren. Mischungen der vorgenannten Salze können ebenfalls benutzt werden.

Die erfindungsgemässen Mund- und Zahnpflegemittel können an sich für derartige Zwecke bekannte Bestandteile in üblichen Mengen enthalten. Hierbei sind insbesondere zu nennen:

Kieselsäurexerogel Aluminiumhydroxid

Verdickungsmittel, wie Natriumcarboxymethylcellulose oder pyrogene Kieselsäure Netzmittel, wie Natriumlaurylsulfat Glycerin

Antiseptika, wie Chlorthymol Süssstoff sowie ätherische Öle.

Die zur Anwendung gelangenden Phosphorverbindungen der oben beschriebenen Art bzw. ihre wasserlöslichen Salze erhält man, wenn man Lactame der Formel

R

worin n 3—5 und R ein Wasserstoffatom oder einen Alkyl-rest mit 1—3 C-Atomen, vorzugsweise eine CH3-Gruppe, bedeuten, mit Phosphortrihalogeniden oder phosphoriger Säure und Phosphortrihalogeniden umsetzt, das Reaktionsprodukt hydrolysiert und gegebenenfalls in die Salze überführt.

Das molare Mengenverhältnis von Lactam/Phosphorver-bindungen bei den verschiedenen Umsetzungen beträgt zwischen 1:2 bis 1:6, vorzugsweise 1:4.

Die Hydrolyse erfolgt zweckmässigerweise durch Zugabe von Wasser zu dem Reaktionsgemisch. Sie kann jedoch ge-wünschtenfalls auch in Gegenwart von Alkali wie insbesondere Natronlauge oder Kalilauge, durchgeführt werden. In vielen Fällen können die neuen Diphosphonsäuren auch in Form ihrer wasserlöslichen Salze wie insbesondere Lithium-, Natrium-, Kalium- und Ammoniumsalze Anwendung finden. Soweit die AzacycIoalkan-2,2-diphosphonsäuren in Form der Säuren anfallen, können sie leicht in die wasserlöslichen Salze, beispielsweise durch partielle oder vollständige Neutralisation mit entsprechenden Basen, überführt werden.

Die Herstellung dieser neuen Verbindungen ist nicht Gegenstand des Patentbegehrens.

Beispiele

Als Grundrezepturen für Zahnpasten sind folgende For-

mulierungen geeignet:

a)

Gewichtsteile

Glycerin

60,0

Wasser

13,5

Natriumcarboxymethylcellulose

0,6

Kieselsäurexerogel

20,0

Natriumlaurylsulfat

2,0

Ätherische Öle

1,0

Süssstoff

0,4

2,2-Diphosphono-1 -azacycloalkan

2,5

b)

Gewichtsteile

Glycerin

30,0

Wasser

18,5

N atri umcarboxymethylcellulose

1,0

Aluminiumhydroxid

44,0

Natriumlaurylsulfat

1,0

Kieselsäurepyrogen

1,5

Ätherische Öle

1,5

Süssstoff

0,5

2,2-Diphosphono-1 -azacycloalkan

2,0

Als Grundrezeptur für Mundwässer ist folgende Kombi nation geeignet:

c)

Gewichtsteile

Äthylalkohol

19,5

Glycerin

7,5

Wasser

70,0

Ätherische Öle

0,2

N atriumlaury lsulfat

0,1

Antiseptikum (Chlorthymol)

0,1

Süssstoff

0,1

2,2-Diphosphono-1 -azacycloalkan

2,5

5

10

15

20

25

30

35

40

45

50

55

60

65

3

615 097

Anstelle von 2,2-Diphosphono-l-azacycloalkan wurde jeweils die angegebene Menge 2,2-Diphosphono-1-azacyclo-pentan, N-Methyl-2,2-diphosphono-l-azacyclopentan, 2,2-Di-phosphono-l-azacyclohexan oder 2,2-Diphosphono-1-azacy-cloheptan verwendet.

Durch den regelmässigen Gebrauch der Zahnpasten und/ oder Mundwässer mit einem Gehalt an 2,2-Diphosphono-1-azacycloalkan der angegebenen Art lässt sich die Bildung von Zahnstein wesentlich verringern. Die Ausbildung von har-5 ten, kompakten Zahnbelägen wird weitgehend verhindert.

CH52779A 1973-08-27 1979-01-18 CH615097A5 (de)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
DE2343196A DE2343196C3 (de)	1973-08-27	1973-08-27	Aiacycloalkan-2^-diphosphonsäuren oder deren wasserlösliche Salze

Publications (1)

Publication Number	Publication Date
CH615097A5 true CH615097A5 (de)	1980-01-15

Family

ID=5890837

Family Applications (2)

Application Number	Title	Priority Date	Filing Date
CH1160374A CH613979A5 (de)	1973-08-27	1974-08-26
CH52779A CH615097A5 (de)	1973-08-27	1979-01-18

Family Applications Before (1)

Application Number	Title	Priority Date	Filing Date
CH1160374A CH613979A5 (de)	1973-08-27	1974-08-26

Country Status (16)

Country	Link
US (1)	US3941772A (de)
JP (1)	JPS5710878B2 (de)
AT (1)	AT326687B (de)
BE (1)	BE819189A (de)
BR (1)	BR7407080D0 (de)
CA (1)	CA1029020A (de)
CH (2)	CH613979A5 (de)
DE (1)	DE2343196C3 (de)
DK (1)	DK157598C (de)
ES (1)	ES429542A1 (de)
FR (1)	FR2245372B1 (de)
GB (1)	GB1451865A (de)
IE (1)	IE39823B1 (de)
IT (1)	IT1020069B (de)
LU (1)	LU70795A1 (de)
NL (1)	NL179908C (de)

Families Citing this family (91)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE2456808A1 (de) *	1974-11-30	1976-08-12	Henkel & Cie Gmbh	Verfahren zum stabilisieren von calcium-hydrogenphosphat-anhydrid gegen die umsetzung mit fluorionen
DE2456666A1 (de) *	1974-11-30	1976-08-12	Henkel & Cie Gmbh	Verfahren zum stabilisieren von calcium-hydrogenphosphat-dihydrat gegen hydrolyse
US4118474A (en) *	1976-08-16	1978-10-03	Colgate-Palmolive Company	Antibacterial oral composition
SE431285B (sv) *	1976-08-16	1984-01-30	Colgate Palmolive Co	Munvardskomposition innehallande en fosfonforening, for minskning av missfergning bildad av ett ingaende kvevehaltigt antibakteriellt plaquehemmande medel
US4118475A (en) *	1976-08-16	1978-10-03	Colgate-Palmolive Company	Antibacterial oral composition
US4118473A (en) *	1976-08-16	1978-10-03	Colgate-Palmolive Company	Antibacterial oral composition
US4118472A (en) *	1976-08-16	1978-10-03	Colgate-Palmolive Company	Antibacterial oral composition
US4118476A (en) *	1976-08-16	1978-10-03	Colgate-Palmolive Company	Antibacterial oral composition
NL7711307A (nl) *	1976-10-19	1978-04-21	Hoechst Ag	Fosforcarbonzuurverbindingen en hun bereiding.
DE2745083C2 (de) *	1977-10-07	1985-05-02	Henkel KGaA, 4000 Düsseldorf	Hydroxydiphosphonsäuren und Verfahren zu deren Herstellung
FR2411810A1 (fr) *	1977-12-14	1979-07-13	Protex Manuf Prod Chimique	Compositions additives pour melanges a base de platre de gypse ou anhydrite
DE3027040A1 (de) *	1980-07-17	1982-02-25	Hoechst Ag, 6000 Frankfurt	Dimethylphosphinyl-alkanphosphonsaeuren, ein verfahren zu ihrer herstellung und ihre verwendung als gipsabbindeverzoegerer
US4466835A (en) *	1983-04-18	1984-08-21	The Dow Chemical Company	Cement compositions containing set retarders
US4466836A (en) *	1983-04-28	1984-08-21	The Dow Chemical Company	Set retarding compounds for use in cement slurries
US4468252A (en) *	1983-06-01	1984-08-28	The Dow Chemical Company	Set retarding additives for cement from aminomethylenephosphonic acid derivatives
US4569838A (en) *	1983-12-23	1986-02-11	Colgate-Palmolive Company	Dentifrice
GB2157279A (en) *	1984-04-12	1985-10-23	Dow Chemical Co	Well treating composition
US4606776A (en) *	1984-09-28	1986-08-19	Salis International, Inc.	Air brush cleaning unit
DE3439094A1 (de) *	1984-10-25	1986-05-07	Henkel KGaA, 4000 Düsseldorf	Mund- und zahnpflegemittel
US4575456A (en) *	1984-11-30	1986-03-11	Colgate-Palmolive Company	Gel dentifrice of desirable consistency
US5104863A (en) *	1984-12-21	1992-04-14	The Procter & Gamble Company	Certain bicycloalkane and azabicycloalkane-1,1-diphosphonic acid derivatives useful for treating diseases associated with abnormal calcium and phosphate metabolism
US4687768A (en) *	1984-12-21	1987-08-18	The Procter & Gamble Company	Certain hexahydroindan-2,2-diphosphonic acids useful in treating diseases associated with abnormal calcium and phosphate metabolism
IL77243A (en) *	1984-12-21	1996-11-14	Procter & Gamble	Pharmaceutical compositions containing geminal diphosphonic acid compounds and certain such novel compounds
JPS62185092A (ja) *	1986-02-07	1987-08-13	Teijin Ltd	新規ホスホン酸誘導体および除草剤
DE3627469A1 (de) *	1986-08-13	1988-02-25	Henkel Kgaa	Verfahren zur ueberfuehrung von organophosphonsaeuren in die alkali- oder ammoniumsalze
US4964917A (en) *	1986-08-26	1990-10-23	Sandoz Ltd.	Methods and compositions for reclaiming concrete
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* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE1958123C3 (de) *	1969-11-19	1978-09-28	Henkel Kgaa, 4000 Duesseldorf	Verfahren zur Herstellung von 1 -Aminoalkan-1,1 -diphosphonsäuren oder deren Salzen

1973
- 1973-08-27 DE DE2343196A patent/DE2343196C3/de not_active Expired
1974
- 1974-08-01 DK DK411774A patent/DK157598C/da not_active IP Right Cessation
- 1974-08-01 NL NLAANVRAGE7410369,A patent/NL179908C/xx not_active IP Right Cessation
- 1974-08-20 US US05/499,000 patent/US3941772A/en not_active Expired - Lifetime
- 1974-08-21 IT IT26461/74A patent/IT1020069B/it active
- 1974-08-23 GB GB3706674A patent/GB1451865A/en not_active Expired
- 1974-08-26 AT AT689574A patent/AT326687B/de active
- 1974-08-26 LU LU70795A patent/LU70795A1/xx unknown
- 1974-08-26 ES ES429542A patent/ES429542A1/es not_active Expired
- 1974-08-26 IE IE1778/74A patent/IE39823B1/xx unknown
- 1974-08-26 CH CH1160374A patent/CH613979A5/xx not_active IP Right Cessation
- 1974-08-26 BR BR7080/74A patent/BR7407080D0/pt unknown
- 1974-08-26 CA CA207,802A patent/CA1029020A/en not_active Expired
- 1974-08-26 BE BE147908A patent/BE819189A/xx not_active IP Right Cessation
- 1974-08-27 JP JP9832074A patent/JPS5710878B2/ja not_active Expired
- 1974-08-27 FR FR7429204A patent/FR2245372B1/fr not_active Expired
1979
- 1979-01-18 CH CH52779A patent/CH615097A5/de not_active IP Right Cessation

Also Published As

Publication number	Publication date
JPS5710878B2 (de)	1982-03-01
DE2343196C3 (de)	1980-01-10
FR2245372A1 (de)	1975-04-25
IT1020069B (it)	1977-12-20
US3941772A (en)	1976-03-02
CA1029020A (en)	1978-04-04
NL7410369A (nl)	1975-03-03
BR7407080D0 (pt)	1975-06-24
NL179908C (nl)	1986-12-01
FR2245372B1 (de)	1978-07-21
DE2343196A1 (de)	1975-04-03
DK157598C (da)	1990-06-11
IE39823L (en)	1975-02-27
CH613979A5 (de)	1979-10-31
ES429542A1 (es)	1976-08-16
IE39823B1 (en)	1979-01-03
AT326687B (de)	1975-12-29
JPS5050366A (de)	1975-05-06
LU70795A1 (de)	1975-06-11
ATA689574A (de)	1975-03-15
DK411774A (de)	1975-04-28
BE819189A (fr)	1975-02-26
GB1451865A (en)	1976-10-06
NL179908B (nl)	1986-07-01
DK157598B (da)	1990-01-29
DE2343196B2 (de)	1979-05-10

Legal Events

Date	Code	Title	Description
1994-10-31	PL	Patent ceased
2024-10-31	PL	Patent ceased

Publication	Publication Date	Title
CH615097A5 (de)	1980-01-15
DE968516C (de)	1958-02-27	Zahnpflegemittel
CH620359A5 (de)	1980-11-28
DE69302413T2 (de)	1996-10-17	Zusammensetzung für die Verwendung in der Mundhöhle
DE1617729A1 (de)	1971-04-08	Zahnsteinbildung verhinderndes Mund- und Zahnpflegemittel
DE1033856B (de)	1958-07-10	Zahnpflegemittel
DE1157737B (de)	1963-11-21	Zahnpflegemittel
CH631074A5 (de)	1982-07-30	Antibakterielles mundpflegemittel.
EP0152836B1 (de)	1990-06-20	Mittel zur oralen Hygiene
EP0179396B1 (de)	1991-08-21	Mund- und Zahnpflegemittel
US2955985A (en)	1960-10-11	Dentifrice compositions
EP0291747A1 (de)	1988-11-23	Zahnpasta
DE69114708T2 (de)	1996-05-02	Mittel gegen zahnstein und zahnbelag, die azacycloalkan-diphosphonsäurederivate enthalten.
EP0236827B1 (de)	1990-05-23	Zahnpasta
CH620358A5 (de)	1980-11-28
US4088752A (en)	1978-05-09	Oral composition for plaque and caries inhibition
DE2953295C2 (de)	1988-11-24
US4122162A (en)	1978-10-24	Oral composition for plaque and caries inhibition
DE1668572B2 (de)	1975-07-31	Dizinn-(ll)-salze von Gem.-Diphosphonsä uren
DE2153821B2 (de)	1978-10-19	Zahnpflegemittel
DE2224560A1 (de)	1973-11-29	Zahnsteinbildung verhindernde mundund zahnpflegemittel
DE3239976A1 (de)	1983-05-11	Gegen zahnstein wirkendes mundpflegemittel
DE1960068C3 (de)	1982-05-13	Zahnpasta mit antikariogener Wirksamkeit
WO1991002510A1 (de)	1991-03-07	Zahnsteinhemmende mund- und zahnpflegemittel
AT332555B (de)	1976-10-11	Mund- und zahnpflegemittel

CH615097A5 - - Google Patents

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ID=5890837

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