WO1991009589A2 - Produit d'hygiene bucco-dentaire - Google Patents
Produit d'hygiene bucco-dentaire Download PDFInfo
- Publication number
- WO1991009589A2 WO1991009589A2 PCT/EP1990/002171 EP9002171W WO9109589A2 WO 1991009589 A2 WO1991009589 A2 WO 1991009589A2 EP 9002171 W EP9002171 W EP 9002171W WO 9109589 A2 WO9109589 A2 WO 9109589A2
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- group
- acid
- phosphoric acid
- carbon atoms
- hydrogen
- 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.)
- Ceased
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Classifications
-
- 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
- A61K8/556—Derivatives containing from 2 to 10 oxyalkylene groups
-
- 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
Definitions
- the invention relates to oral and dental care products with improved activity against tooth decay by virtue of a content of an active ingredient which reduces the solubility of hydroxylapatite and inhibits crystal growth and the phosphate ion exchange of hydroxylapatite.
- Oral and dental care products are products that serve to clean and care for the teeth, the oral cavity and the throat.
- your job is to prevent dental diseases such as tooth decay and periodontal disease and to prevent the formation of tartar.
- water-soluble organic phosphates have a caries-prophylactic effect.
- mono- and disodium glycerophosphate, fructose-6-phosphate, sorbitol-6-phosphate, glucose-1-phosphate and glucose-6-phosphate have been proposed as additives to oral and dental care products.
- Salts of phosphoric acid esters of lactose and sucrose have also been described as cariostatic components. Although these products have a certain action which reduces the solubility of the hydroxyapatite and inhibits crystal growth, the effects are not sufficient for effective protection against demineralization of the tooth enamel.
- Phosphoric acid esters according to formula (I) are further understood to mean both the phosphoric acid esters of cycloalkane carboxylic acids according to formula (I) and the phosphoric acid esters of the cycloalkenecarboxylic acids mentioned and the salts of cycloalkane and cycloalkenecarboxylic acids mentioned.
- These compounds can be prepared from known polyhydroxycycloalkanoic or alkenecarboxylic acids.
- alkylene oxides with 2 to 5 carbon atoms i.e. ethylene oxide, propylene oxide, butylene oxide, isobutylene oxide and pentene oxide
- ethylene oxide, propylene oxide, butylene oxide, isobutylene oxide and pentene oxide are added to the polyhydroxycycloalkane or -alkenecarboxylic acids using processes known from the literature, i.e. using basic catalysts such as NaOH, KOH, Na methylate , Ca acetate or acidic catalysts such as boron trifluoride, antimony pentachloride, triethyloxonium fluoroborate or SnCl 4 .
- basic catalysts such as NaOH, KOH, Na methylate , Ca acetate
- acidic catalysts such as boron trifluoride, antimony pentachloride, triethyloxonium fluoroborate or SnCl 4 .
- no uniform products are obtained when n mol of alkylene oxide is added to
- the phosphorylation of the polyhydroxycycloalkane and alkenecarboxylic acids and their alkylene oxide addition products can be carried out, for example, by reaction with phosphorus pentoxide or polyphosphoric acid with a high content of phosphorus pentoxide, e.g. by the method described in U.S. Patent 4,311,662.
- phosphorus pentoxide or polyphosphoric acid with a high content of phosphorus pentoxide e.g. by the method described in U.S. Patent 4,311,662.
- both predominantly monophosphoric esters and predominantly those compounds can be prepared in which the majority of the OH groups of the polyhydroxycycloalkane or alkenecarboxylic acids are phosphorylated.
- a brief hydrolytic treatment in the acidic pH range is advantageous, since P-O-P bonds that are still present are split. This has an advantageous effect on the storage stability of the formulated products.
- Detailed synthesis instructions can be found in the examples.
- the products contain inorganic phosphates as a by-product, predominantly orthophosphate, which is not detrimental to the cariostatic activity of the products and can therefore remain in the product.
- the degree of phosphorylation PG i.e. the number of phosphorylated OH groups divided by the number of OH groups available for phosphorylation, can be determined from the analytical values for the content of inorganic phosphate and the total phosphate content as well as the amounts of substrate and phosphorylation agent used ( For example, phosphorus pentoxide) can be calculated
- the phosphoric acid esters of polyhydroxycycloalkane or alkenecarboxylic acids can be neutralized with inorganic or organic bases and in this way converted into physiologically compatible, water-soluble salts.
- Preferred alkyleneoxy groups (OC n H 2n ) are the ethyleneoxy and the propyleneoxy group.
- Preferred phosphoric acid esters according to formula (I) are the alkali metal salts, especially the sodium and potassium salts.
- the oral and dental care products according to the invention containing phosphoric acid esters of the formula (I) can be prepared in the various designs customary for such products, for example as mouthwashes, toothpastes or tooth powder.
- the content of phosphoric acid esters according to formula (I) should be in the range from 0.05 to 5.0% by weight of the preparation. However, amounts of 0.1-2% by weight are usually sufficient in toothpastes, tooth powders and tooth gels to achieve a significant caries-inhibiting effect. In mouthwashes to be used undiluted, sufficient effects can be achieved with 0.05-1.0% by weight, in mouthwashes that are diluted before use with higher concentrations in accordance with the intended dilution ratio.
- Oral and dental care products can also be prepared in the form of chewing gum, mouth lozenges and dental treatment ointments.
- Such oral care products which may be used several times a day and inevitably swallowed, may also contain the phosphoric acid esters of the formula (I). In these cases, however, the dosage should not exceed 1% by weight of the preparation.
- Particularly suitable cleaning bodies for the toothpastes according to the invention are, in particular, finely divided xerogel silicas, hydro gel silicas, precipitated silicas, aluminum oxide trihydrate and finely divided aluminum oxide or mixtures of these cleaning agents in amounts of 15-40% by weight of the toothpaste.
- Low molecular weight polyethylene glycols, glycerol, sorbitol or mixtures of these products in amounts of up to approx. 50% by weight are mainly suitable as humectants.
- the thickeners finely divided silica gels and hydrocolloids, such as carboxymethyl cellulose, hydroxyethyl cellulose, hydroxypropyl guar, hydroxyethyl starch, polyvinyl pyrrolidone, high molecular weight polyethylene glycol, plant gums such as tragacanth, agar-agar, carrageenan, gum arabic, xantham gum, and carboxyvinyl polymers (for example Carbopol (R ) Types).
- silica gels and hydrocolloids such as carboxymethyl cellulose, hydroxyethyl cellulose, hydroxypropyl guar, hydroxyethyl starch, polyvinyl pyrrolidone, high molecular weight polyethylene glycol, plant gums such as tragacanth, agar-agar, carrageenan, gum arabic, xantham gum, and carboxyvinyl polymers (for example Carbopol (R ) Types).
- anionic high-foaming surfactants such as, for example, linear sodium alkyl sulfates with 12-18 C atoms in the alkyl group, sodium salts of alkyl polyglycol ether sulfates with 12-16 C atoms in the linear alkyl group and 2-6 glycol ether groups in the molecule, of alkyl, (C 12-16 ) benzene sulfonate, linear alkane (C 12-18 ) sulfonates, sulfosuccinic acid monoalkyl (C 12-18 ) esters, sulfated fatty acid monoglycerides, sulfated fatty acid alkanolamides, sulfoacetic acid alkyl (C 12-18 ) esters, acyl sarcosides , Acyl taurides and acyl isethionates each containing 8-18 C atoms in the acyl group.
- anionic high-foaming surfactants such
- Nonionic surfactants are also suitable, for example oxyethylates of fatty acid mono- and diglycerides, fatty acid-sorbitan esters and ethylene oxide-propylene oxide block polymers.
- alkyl glycosides of the general formula RO- (G) x can also be used as nonionic surfactants, in which R is a primary straight-chain or aliphatic radical which has 10 to 22, preferably 12 to 18, C atoms and is methyl branched in the G position Is symbol that stands for a glycose unit with 5 or 6 carbon atoms, and the degree of oligomerization x is between 1 and 10.
- R is a primary straight-chain or aliphatic radical which has 10 to 22, preferably 12 to 18, C atoms and is methyl branched in the G position Is symbol that stands for a glycose unit with 5 or 6 carbon atoms, and the degree of oligomerization x is between 1 and 10.
- Other common toothpaste additives are:
- Anti-calculus agents e.g. Organophosphonates such as 1-hydroxyethane-1,1-diphosphonic acid, 1-phosphonopropane-1,2,3-tricarboxylic acid and others e.g. from US-PS 3,488,419, DE-OS 2224430 and DE-OS 2343 196 are known;
- caries-inhibiting substances such as Sodium fluoride, sodium monofluorophosphate, tin fluoride,
- Sweeteners such as Saccharin sodium, sodium cyclamate, aspartame, glycyrrhizin, glycyrrhetinic acid, sucrose, lactose, maltose, fructose,
- Flavors such as Peppermint oil, spearmint oil, eucalyptus oil, anise oil, fennel oil, caraway oil, menthyl acetate, cinnamaldehyde, anethole, vanillin, thymol and mixtures of these and other natural and synthetic flavors,
- Buffer substances such as primary, secondary or tertiary alkali phosphates or citric acid / sodium citrate, wound healing and anti-inflammatory substances such as allantoin, urea, azulene, chamomile active ingredients and acetylsalicylic acid derivatives.
- alkylene oxides to the polyhydroxycycloalkane and -alkenecarboxylic acids was carried out by a process known from the literature by reaction in a pressure vessel in the presence of catalytically active amounts of sodium methylate at a temperature of 100-150 ° C.
- the products were characterized by determining the hydroxyl number (OHZ).
- the active substance content of the solutions was determined after the
- % Active ingredient 100% -% phosphate inorganic
- the effectiveness of the substances according to the invention is determined with regard to a) the reduction in hydroxylapatite solubility (ALR), b) the inhibition of hydroxylapatite crystal growth (KWI) and c) the inhibition of the hydroxylapatite-phosphate ion exchange capacity (PIA).
- hydroxylapatite powder (specific surface area 60 m 2 / g, from Merck) was placed in a reaction vessel thermostatted at 37 ° C. with 300 ml of demineralized water.
- the amount of 0.1 M lactic acid solution used for pH stabilization was obtained from a writer registered.
- the lactic acid consumption registered after 2 hours corresponded to the solubility of the untreated hydroxylapatite (Lu).
- the measurement was carried out analogously to a). Before the pH was adjusted, 6 mg of the active ingredient to be tested were dissolved.
- Precipitated silica 18% by weight
- Active ingredient 1 1.0% by weight
- Carboxymethyl cellulose 3 0.9% by weight
- Aromatic oils 1.0% by weight
- Aroma oil 0.3% by weight
- Sorbitol (70% aqueous solution) 8.0% by weight methyl p-hydroxybenzoate 0.16% by weight
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- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Birds (AREA)
- Epidemiology (AREA)
- Oral & Maxillofacial Surgery (AREA)
- Cosmetics (AREA)
Abstract
Des produits d'hygiène bucco-dentaire à action améliorée contre la formation de caries comprennent comme substance active un ester phosphorique d'un acide carboxylique de cycloalcane ou d'un sel d'un acide carboxylique de cycloalcane de formule générale (I) dans laquelle z désigne un nombre entier de 4 à 7, les différents groupes R représentent, indépendamment les uns des autres, de l'hydrogène ou -(OCnH2n)m-OR2, n étant un nombre entier de 2 à 5, n un nombre de 0 à 8 et R2 de l'hydrogène ou un groupe -PO¿3?M2 et M désigne l'hydrogène, un ion de métal alcalin ou alcalino-terreux, un groupe ammonium ou un groupe mono-, di- ou trihydroxyalkylammonium avec 2 à 4 atomes de carbone dans le groupe hydroxyalkyle, avec au moins trois des groupes R représentant -(OCnH2n)m-OR?2¿ et au moins un groupe R2 = -PO¿3?M2 présent dans la molécule et/ou un ester phosphorique d'un acide carboxylique de cycloalcène ou d'un sel d'un acide carboxylique de cycloalcène, produit formellement à partir des composés selon la formule (I) par disparition d'un atome d'hydrogène au niveau de deux atomes de carbone voisins et formation d'une liaison double C=C entre ces deux atomes de carbone. On emploie de préférence l'acide quinique et l'acide shikimique phosphorylés et, le cas échéant, éthoxylés sous la forme de leurs sels alcalins.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19893942688 DE3942688A1 (de) | 1989-12-22 | 1989-12-22 | Mund- und zahnpflegemittel |
| DEP3942688.2 | 1989-12-22 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| WO1991009589A2 true WO1991009589A2 (fr) | 1991-07-11 |
| WO1991009589A3 WO1991009589A3 (fr) | 1991-10-31 |
Family
ID=6396265
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PCT/EP1990/002171 Ceased WO1991009589A2 (fr) | 1989-12-22 | 1990-12-13 | Produit d'hygiene bucco-dentaire |
Country Status (2)
| Country | Link |
|---|---|
| DE (1) | DE3942688A1 (fr) |
| WO (1) | WO1991009589A2 (fr) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2013091775A2 (fr) | 2011-12-21 | 2013-06-27 | Merck Patent Gmbh | Utilisation de dérivés du cyclohéxanol comme principes actifs antimicrobiens |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR101162251B1 (ko) * | 2004-09-14 | 2012-07-04 | 에스티 라우더 코디네이션 센터 엔.브이. | 포스포릴화된 폴리페놀류를 함유하는 국소용 조성물 |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB8908700D0 (en) * | 1989-04-18 | 1989-06-07 | Ici Plc | Compounds |
-
1989
- 1989-12-22 DE DE19893942688 patent/DE3942688A1/de not_active Withdrawn
-
1990
- 1990-12-13 WO PCT/EP1990/002171 patent/WO1991009589A2/fr not_active Ceased
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2013091775A2 (fr) | 2011-12-21 | 2013-06-27 | Merck Patent Gmbh | Utilisation de dérivés du cyclohéxanol comme principes actifs antimicrobiens |
| US9492364B2 (en) | 2011-12-21 | 2016-11-15 | Merck Patent Gmbh | Use of cyclohexanol derivatives as antimicrobial active compounds |
| USRE46698E1 (en) | 2011-12-21 | 2018-02-06 | Merck Patent Gmbh | Use of cyclohexanol derivatives as antimicrobial active compounds |
| US10071037B2 (en) | 2011-12-21 | 2018-09-11 | Merck Patent Gmbh | Use of cyclohexanol derivatives as antimicrobial active compounds |
Also Published As
| Publication number | Publication date |
|---|---|
| WO1991009589A3 (fr) | 1991-10-31 |
| DE3942688A1 (de) | 1991-06-27 |
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