US4820507A
Expired / Lapsed
US
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Oral and dental hygiene preparations
Assignee: Henkel AG and Co KGaA
•
Filing: 1987-03-02
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Granted: 1989-04-11
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Expires: 2007-03-02
Abstract
Abstract Oral and dental hygiene preparations containing quaternary ammonium compounds of the formula ##STR1## wherein R 1 is an n-alkyl group, preferably containing from 8 to 12 carbon atoms, R 2 is hydrogen, a CH 3 -group or a CH 2 OH-group and R 3 is a CH 3 -group or a group of the formula --CH 2 --CH(OH)--R 2 , A is an inorganic or organic acid anion and n is the basicity of the anion. The quaternary ammonium compounds of formula I can have a plaque inhibiting effect and show only slight antimicrobial activity. R 1 is preferably an n-decyl group, R 2 is hydrogen and R 3 is a CH 3 -group or a 2-hydroxyethyl group. The oral and dent al hygiene preparations also preferably contain fluorides and/or organophosphonates as the anion A.
Inventors
- 👤 Hans-Juergen Klueppel
- 👤 Walter Ploeger
- 👤 Horst Rutzen
- 👤 Rudolf Lehmann
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-01 19:33
CPC Classifications
A; A61; A61K; A61K8/00; A61K8/18; A61K8/30; A61K8/40; A61K8/41; A61K8/416; A61K8/55; A61Q; A61Q11/00
Claims Analysis
Total Claims: 35
Claim 1
Independent Claim
127 words
An oral and dental hygiene composition for the care of the oral cavity of a mammal comprising a quaternary ammonium compound of the formula ##STR6## wherein; R 1 is C 8 -C 12 -n-alkyl; R 2 is hydrogen, --CH 3 or --CH 2 OH; R 3 is --CH 3 or --CH 2 CH(OH)--R 2 ; A is an inorganic or organic anion which forms a water-soluble salt with the quaternary ammonium compound which is physiologically compatible with the oral cavity of said mammal; and n is the basicity of the anion A; and wherein said quaternary ammonium compound is present in the hygiene composition in an amount effective to significantly inhibit the formation of dental plaque and ineffective to significantly inhibit microbial activity in the oral cavity.
Claim 2
Dependent Claim
127 words
An oral and dental hygiene composition for the care of the oral cavity of a mammal comprising a quaternary ammonium compound of the formula ##STR6## wherein; R 1 is C 8 -C 12 -n-alkyl; R 2 is hydrogen, --CH 3 or --CH 2 OH; R 3 is --CH 3 or --CH 2 CH(OH)--R 2 ; A is an inorganic or organic anion which forms a water-soluble salt with the quaternary ammonium compound which is physiologically compatible with the oral cavity of said mammal; and n is the basicity of the anion A; and wherein said quaternary ammonium compound is present in the hygiene composition in an amount effective to significantly inhibit the formation of dental plaque and ineffective to significantly inhibit microbial activity in the oral cavity.
Claim 3
Dependent Claim
25 words
The composition of claim 1, wherein said compound is present in an amount of from about 0.01% to about 2.0% by weight of the composition.
Claim 4
Dependent Claim
25 words
The composition of claim 2, wherein said compound is present in an amount of from about 0.03% to about 2.0% by weight of the composition.
Claim 5
Dependent Claim
10 words
The composition of claim 1, wherein R 1 in n-decyl.
Claim 6
Dependent Claim
9 words
The composition of claim 4, wherein A is fluoride.
Claim 7
Dependent Claim
18 words
The composition of claim 4, wherein R 2 is hydrogen and R 3 is CH 3 or 2-hydroxyethyl.
Claim 8
Dependent Claim
9 words
The composition of claim 6, wherein A is fluoride.
Claim 9
Dependent Claim
9 words
The composition of claim 6, wherein A is organophosphonate.
Claim 10
Dependent Claim
177 words
The composition of claim 8, wherein A is an organophosphonate anion of an organophosphonic acid of the formula II or III ##STR7## in which R 4 is alkyl containing from 1 to 6 carbon atoms, hydroxyl, amino, --NHR 8 , wherein R 8 is alkyl containing from 1 to 3 carbon atoms, or --CH 2 --COOH, --CH 2 PO 3 H 2 , --CH 2 --CH 2 --PO 3 H 2 , --CH(PO 3 H 2 )(OH) or --CH 2 --CH--(PO 3 H 2 ) 2 ; R 5 is hydrogen, alkyl containing from 1 to 6 carbon atoms or, where R 4 is amino or --NHR 8 , forms a 5- to 7-membered azacycloalkane ring with the nitrogen atom and the central carbon atom; R 6 is --PO 3 H 2 , --CR 7 (COOH)(PO 3 H 2 ), --CR 7 (PO 3 H 2 ) 2 or --CR 7 (COOH)--CH 2 --PO 3 H 2 ; and R 7 is hydrogen, alkyl containing from 1 to 4 carbon atoms, or --(CH 2 ) 1-2 --COOH.
Claim 11
Dependent Claim
12 words
The composition of claim 9, wherein R 7 is CH 3 .
Claim 12
Dependent Claim
9 words
The composition of claim 4, wherein A is organophosphonate.
Claim 13
Dependent Claim
179 words
The composition of claim 11, wherein A is an organophosphonate anion of an organosphosphonic acid of the formula II or III ##STR8## in which R 4 is alkyl containing from 1 to 6 carbon atoms, hydroxyl, amino group, --NHR 8 , wherein R 8 is alkyl containing from 1 to 3 carbon atoms, or --CH 2 --COOH, --CH 2 PO 3 H 2 , --CH 2 --CH 2 --PO 3 H 2 , --CH(PO 3 H 2 )(OH) or --CH 2 --CH(PO 3 H 2 ) 2 ; R 5 is hydrogen, alkyl containing from 1 to 6 carbon atoms or, where R 4 is amino or --NHR 8 , forms a 5- to 7-membered azacycloalkane ring with the nitrogen atom and the central carbon atom; R 6 is --PO 3 H 2 , --CR 7 (COOH)(PO 3 H 2 ), --CR 7 (PO 3 H 2 ) 2 , or --CR 7 (COOH)--CH 2 --PO 3 H 2 ; and R 7 is hydrogen, alkyl containing from 1 to 4 carbon atoms, or --(CH 2 ).sub. 1-2 --COOH.
Claim 14
Dependent Claim
12 words
The composition of claim 12, wherein R 7 is CH 3 .
Claim 15
Dependent Claim
18 words
The composition of claim 1, wherein R 2 is hydrogen and R 3 is CH 3 or 2-hydroxyethyl.
Claim 16
Dependent Claim
9 words
The composition of claim 14, wherein A is fluoride.
Claim 17
Dependent Claim
9 words
The composition of claim 14, wherein A is organophosphonate.
Claim 18
Dependent Claim
177 words
The composition of claim 16, wherein A is an organophosphononate anion of an organophosphonic acid of the formula II or III ##STR9## in which R 4 is alkyl containing from 1 to 6 carbon atoms, hydroxyl, amino, --NHR 8 , wherein R 8 is alkyl containing from 1 to 3 carbon atoms, or --CH 2 --COOH, --CH 2 PO 3 H 2 , --CH 2 --CH 2 --PO 3 H 2 , --CH(PO 3 H 2 )(OH) or --CH 2 --CH--(PO 3 H 2 ) 2 ; R 5 is hydrogen, alkyl containing from 1 to 6 carbon atoms or, where R 4 is amino or --NHR 8 , forms a 5- to 7-membered azacycloalkane ring with the nitrogen atom and the central carbon atom; R 6 is --PO 3 H 2 , --CR 7 (COOH)(PO 3 H 2 ), --CR 7 (PO 3 H 2 ) 2 or --CR 7 (COOH)--CH 2 --PO 3 H 2 ; and R 7 is hydrogen, alkyl containing from 1 to 4 carbon atoms, or --(CH 2 ).sub. 1-2 --COOH.
Claim 19
Dependent Claim
12 words
The composition of claim 17, wherein R 7 is CH 3 .
Claim 20
Dependent Claim
9 words
The composition of claim 1, wherein A is fluoride.
Claim 21
Dependent Claim
9 words
The composition of claim 1, wherein A is organophosphonate.
Claim 22
Dependent Claim
177 words
The composition of claim 20, wherein A is an organophosphonate anion of an organophosphonic acid of the formula II or III ##STR10## in which R 4 is alkyl containing from 1 to 6 carbon atoms, hydroxyl, amino, --NHR 8 , wherein R 8 is alkyl containing from 1 to 3 carbon atoms, or --CH 2 --COOH, --CH 2 PO 3 H 2 , --CH 2 --CH 2 PO 3 H 2 , --CH(PO 3 H 2 )(OH) or --CH 2 --CH--(PO 3 H 2 ) 2 ; R 5 is hydrogen, alkyl containing from 1 to 6 carbon atoms or, where R 4 is amino or --NHR 8 , forms a 5- to 7-membered azacycloalkane ring with the nitrogen atom and the central carbon atom; R 6 is --PO 3 H 2 , --CH 7 (COOH)(PO 3 H 2 ), --CR 7 (PO 3 H 2 ) 2 or --CR 7 (COOH)--CH 2 --PO 3 H 2 ; and R 7 is hydrogen, alkyl containing from 1 to 4 carbon atoms, or --(CH 2 ) 1-2 --COOH.
Claim 23
Dependent Claim
12 words
The composition of claim 21, wherein R 7 is CH 3 .
Claim 24
Dependent Claim
41 words
The hygiene composition of claim 1 wherein the composition is a mouthwash further comprising an aqueous or aqueous-alcoholic solution, and wherein the quaternary ammonium compound is present in an amount of from about 0.03 to 0.3% by weight of the mouthwash.
Claim 25
Dependent Claim
10 words
The composition of claim 23, wherein R 1 is n-decyl.
Claim 26
Dependent Claim
18 words
The composition of claim 23, wherein R 2 is hydrogen and R 3 is CH 3 or 2-hydroxyethyl.
Claim 27
Dependent Claim
9 words
The composition of claim 23, wherein A is fluoride.
Claim 28
Dependent Claim
176 words
The mouthwash of claim 23, wherein A is an organophosphonate anion of an organophosphonic acid of the formula II or III ##STR11## in which R 4 is alkyl containing from 1 to 6 carbon atoms, hydroxyl, amino, --NHR 8 , wherein R 8 is alkyl containing from 1 to 3 carbon atoms, or --CH 2 --COOH, --CH 2 PO 3 H 2 , --CH 2 --CH 2 --PO 3 H 2 , --CH(PO 3 H 2 )(OH) or --CH 2 --CH--(PO 3 H 2 ) 2 ; R 5 is hydrogen, alkyl containing from 1 to 6 carbon atoms or, where R is amino or --NHR 8 forms a 5- to 7-membered azacycloalkane ring with the nitrogen atom and the central carbon atom; R 6 is --PO 3 H 2 , --CH 7 (COOH)(PO 3 H 2 ), --CR 7 (PO 3 H 2 ) 2 or --CR 7 (COOH)--CH 2 --PO 3 H 2 ; and R 7 is hydrogen, alkyl containing from 1 to 4 carbon atoms, or --(CH 2 ) 1-2 -- COOH.
Claim 29
Dependent Claim
69 words
The hygiene composition of claim 1 wherein the composition is a toothpaste further comprising a dental abrasive in an amount of from about 15 to about 40% by weight of the toothpaste, and a humectant in an amount up to about 50% by weight of the toothpaste, and wherein the quaternary ammonium compound is present in an amount of from about 0.1 to 0.5% by weight of the toothpaste.
Claim 30
Dependent Claim
176 words
The toothpaste of claim 28, wherein A is an organophosphonate anion of an organophosphonic acid of the formula II or III ##STR12## in which R 4 is alkyl containing from 1 to 6 carbon atoms, hydroxyl, amino, --NHR 8 , wherein R 8 is alkyl containing from 1 to 3 carbon atoms, or --CH 2 --COOH, --CH 2 PO 3 H 2 , --CH 2 --CH 2 --PO 3 H 2 , --CH(PO 3 H 2 )(OH) or --CH 2 --CH--(PO 3 H 2 ) 2 ; R 5 is hydrogen, alkyl containing from 1 to 6 carbon atoms or, where R 4 is amino or --NHR 8 , forms a 5- to 7-membered azacycloalkane ring with the nitrogen atom and the central carbon atom; R 6 is --PO 3 H 2 , --CH 7 (COOH)(PO 3 H 2 ), --CR 7 (PO 3 H 2 ) or --CR 7 (COOH)--CH 2 --PO 3 H 2 ; and R 7 is hydrogen, alkyl containing from 1 to 4 carbon atoms, or --(CH 2 ) 1-2 --COOH.
Claim 31
Dependent Claim
28 words
The composition of claim 29, further comprising an ethoxylated sorbitan fatty acid ester, an ethoxylated glycerol fatty acid ester, an alkyl glucoside, or a fatty alcohol polyglycol ester.
Claim 32
Dependent Claim
28 words
The composition of claim 28, wherein the polish comprises a particulate xerogel silicate, a hydrogel silica, a precipitated silica, an aluminum oxide trihydrate, or a particulate -aluminum oxide.
Claim 33
Dependent Claim
10 words
The composition of claim 28, wherein R 1 is n-decyl.
Claim 34
Dependent Claim
18 words
The composition of claim 28, wherein R 2 is hydrogen and R 3 is CH 3 or 2-hydroxyethyl.
Claim 35
Dependent Claim
9 words
The composition of claim 28, wherein A is fluoride.
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USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1992-04-10 | 1992-10-10 | 1993-04-11 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1996-04-10 | 1996-10-10 | 1997-04-11 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 2000-04-10 | 2000-10-10 | 2001-04-11 | $7700.00 | Window Closed / Lapsed |