WO2000016735A1 - Verwendung von monoglycerid(ether)sulfaten und chitosan in mund- und zahnpflegemitteln - Google Patents
Verwendung von monoglycerid(ether)sulfaten und chitosan in mund- und zahnpflegemitteln Download PDFInfo
- Publication number
- WO2000016735A1 WO2000016735A1 PCT/EP1999/006612 EP9906612W WO0016735A1 WO 2000016735 A1 WO2000016735 A1 WO 2000016735A1 EP 9906612 W EP9906612 W EP 9906612W WO 0016735 A1 WO0016735 A1 WO 0016735A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- weight
- monoglyceride
- sulfates
- ether
- alkyl
- Prior art date
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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
- A61K8/60—Sugars; Derivatives thereof
- A61K8/604—Alkylpolyglycosides; Derivatives thereof, e.g. esters
-
- 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
- A61K8/46—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing sulfur
- A61K8/463—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing sulfur containing sulfuric acid derivatives, e.g. sodium lauryl sulfate
-
- 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
- A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
- A61K8/73—Polysaccharides
- A61K8/736—Chitin; Chitosan; Derivatives thereof
-
- 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 is in the field of oral and dental hygiene and relates to the use of preparations containing monoglyceride (etf ⁇ er) sulfates and chitosans for the manufacture of oral and dental care products and toothpastes of a defined composition.
- monoglyceride etf ⁇ er
- oral and dental care products is understood on the one hand by those skilled in the art to be liquid preparations which disinfect the mouth and throat as mouthwash, and on the other hand means pasty or, for some time now, gel-like tooth cleaning agents.
- These preparations have in common the requirement by the consumer to be particularly compatible with the mucous membrane, in order not to give rise to irritation, particularly in the case of minor injuries in the mouth or throat.
- dentifrices there is also the fact that the preparations have to be strong in foam, neutral in taste and active in cleaning.
- German patent application DE-A1 4406748 (Henkel), from which oral and dental care products are known, the surfactant component of which is mainly formed by monoglyceride sulfates and alkyl glucosides. It is disadvantageous, however, that these prior art agents are not entirely satisfactory in terms of compatibility with the oral mucosa, foam stability and cleaning performance. Another particular problem is to disperse abrasives in toothpastes and in particular tooth gels in such a way that neither agglomeration nor separation takes place even when the temperature is stored.
- the object of the invention was therefore to remedy the disadvantages of the prior art and, in particular, to provide oral and dental care products, especially toothpastes, which at the same time have an optimized tolerance to the oral mucosa, improved foam and cleaning performance, and in particular one Characterize stable distribution of the abrasive body. Description of the invention
- the invention relates to the use of mixtures containing
- chitosan or chitosan derivatives to known oral and dental care products containing monoglyceride (ether) sulfates and optionally alkyl glucosides as the main surfactant component not only improves the tolerance to the oral mucosa, but also supports the removal of plaque, stabilizes the foam and in particular a homogeneous and storage-stable distribution of abrasives.
- monoglyceride (ether) sulfates and optionally alkyl glucosides as the main surfactant component not only improves the tolerance to the oral mucosa, but also supports the removal of plaque, stabilizes the foam and in particular a homogeneous and storage-stable distribution of abrasives.
- Monoglyceride sulfates and monoglyceride ether sulfates, which form component (a), are known anionic surfactants which can be obtained by the relevant methods of preparative organic chemistry.
- the usual starting point for their production is triglycerides, which, if appropriate, are transesterified to the monoglycerides after ethoxylation and subsequently sulfated and neutralized.
- suitable sulfating agents preferably gaseous sulfur trioxide or chlorosulfonic acid [cf. EP-B1 0561825, EP-B1 0561999 (Henkel)].
- the neutralized substances can be subjected to ultrafiltration in order to reduce the electrolyte content to a desired level [DE-A1 4204700 (Henkel)].
- Overviews of the chemistry of the monoglyceride sulfates are, for example, by A.K.Biswas et al. in J.Am.Oil.Chem.Soc. 37, 171 (1960) and F.U.Ahmed J.Am.Oil.Chem.Soc. 67, 8 (1990).
- the onoglyceride (ether) sulfates to be used in accordance with the invention follow the formula (I)
- R 1 CO stands for a linear or branched acyl radical with 6 to 22 carbon atoms, x, y and z in total for 0 or for numbers from 1 to 30, preferably 2 to 10, and X stands for an alkali or alkaline earth metal.
- Typical examples of monoglyceride (ether) sulfates which are suitable for the purposes of the invention are the reaction products of lauric acid monoglyceride, coconut fatty acid monoglyceride, palmitic acid monoglyceride, stearic acid monoglyceride, oleic acid monoglyceride and tallow fatty acid monoglyceride and their ethylene oxide adducts or sulfuric acid sulfonate formate with their sulfonate adduct in theirsulfonate adducts with their sulfonic acid adduct and their sulfonate formate with their sulfonic acid adduct and their ethylene oxide adducts with sulfuric acid and their sulfonate adducts with their sulfonic acid adducts and their sulfonate formate with their sulfonate adducts with their sulfonic acid trioxide and its sulf
- Chitosans (component b) are biopolymers and belong to the group of hydrocolloids. From a chemical point of view, these are partially deacetylated chitins of different molecular weights that contain the following - idealized - monomer unit:
- chitosans are cationic biopolymers under these conditions.
- the positively charged chitosans can interact with oppositely charged surfaces and are therefore used in cosmetic hair and body care products and pharmaceuticals Preparations used (cf. Ullmann 's Encyclopedia of Industrial Chemistry, 5th Ed., Vol. A6, Weinheim, Verlag Chemie, 1986, pp. 231-332).
- Overviews on this topic have also been published, for example, by B. Gesslein et al. in HAPPI 27, 57 (1990), O.Skaugrud in Drug Cosm. Ind. 148: 24 (1991) and E. Onoyen et ai.
- chitosans is based on chitin, preferably the shell remains of crustaceans, which are available in large quantities as cheap raw materials.
- the chitin is used in a process that was first developed by Hackmann et al. has been described, usually first deproteinized by adding bases, demineralized by adding mineral acids and finally deacetylated by adding strong bases, the molecular weights being above one wide range can be distributed. Appropriate methods are, for example, made from Makromol. Chem. 177, 3589 (1976) or French patent application FR-A 2701266.
- Preferred types are those as disclosed in German patent applications DE-A1 4442987 and DE-A1 19537001 (Henkel), which have an average molecular weight of 800,000 to 1,200,000 Daltons, a Brookfield viscosity (1% by weight ig in glycolic acid) below 5000 mPas, have a degree of deacetylation in the range from 80 to 88% and an ash content of less than 0.3% by weight.
- anionically or nonionically derivatized chitosans such as, for example, carboxylation, succinylation or alkoxylation products, as described, for example, in German patent DE-C2 3713099 (LOreal) and US Pat German patent application DE-A1 19604180 (Henkel) can be described.
- Alkyl and alkenyl oligoglycosides, which form the optional component (c), are known nonionic surfactants which follow the formula (II),
- R 2 is an alkyl and / or alkenyl radical having 4 to 22 carbon atoms
- G is a sugar radical having 5 or 6 carbon atoms
- p is a number from 1 to 10. They can be obtained according to the relevant procedures in preparative organic chemistry. Representative of the extensive literature here is the review by Biermann et al. in Starch /force 45, 281 (1993), B.Salka in Cosm.Toil. 108, 89 (1993) and J.Kahre et al. in S ⁇ FW-Journal Issue 8, 598 (1995).
- the alkyl and / or alkenyl oligoglycosides can be derived from aldoses or ketoses with 5 or 6 carbon atoms, preferably glucose.
- the preferred alkyl and / or alkenyl oligoglycosides are thus alkyl and / or alkenyl oligoglucos.de.
- Alkyl and / or alkenyl oligoglycosides with an average degree of oligomerization p of 1.1 to 3.0 are preferably used. From an application point of view, those alkyl and / or alkenyl oligoglycosides are preferred whose Degree of oligomerization is less than 1.7 and is in particular between 1.2 and 1.4.
- the alkyl or alkenyl radical R 2 can be derived from primary alcohols having 4 to 11, preferably 8 to 10, carbon atoms.
- Typical examples are butanol, capro alcohol, caprylic alcohol, capric alcohol and undecyl alcohol and their technical mixtures, such as are obtained, for example, in the hydrogenation of technical fatty acid methyl esters or in the course of the hydrogenation of aldehydes from Roelen's oxosynthesis.
- the alkyl or alkenyl radical R 2 can also be derived from primary alcohols having 12 to 22, preferably 12 to 14, carbon atoms.
- Typical examples are lauryl alcohol, myristyl alcohol, cetyl alcohol, palmoleyl alcohol, stearyl alcohol, isostearyl alcohol, oleyl alcohol, alaidyl alcohol, petroselinyl alcohol, arachyl alcohol, gadoleyl alcohol, behenyl alcohol, erucyl alcohol, brassidyl alcohol and the technical mixtures described above, which can be obtained as well as their technical mixtures.
- Alkyl oligoglucosides based on hardened Ci2 / ⁇ 4 coco alcohol with a DP of 1 to 3 are preferred.
- the weight ratio between monoglyceride (ether) sulfates and alkyl and / or alkenyl oligoglycosides can be 90:10 to 10:90, preferably 75:25 to 25: 75 and in particular 60: 40 to 40: 60.
- the preparations can contain further mild co-surfactants than there are, for example: fatty alcohol polyglycol ether sulfates, mono- and / or dialkyl sulfosuccinates, fatty acid isethionates, fatty acid sarcosinates, fatty acid taurides, fatty acid glutamates, ether carboxylic acids, fatty acid glucamides, alkyl or condensate fatty acids, and alkoxylate fatty acid fatty acids, and / or alkyl amide fatty acid fatty acids, and / or alkyl amide fatty acid fatty acids based on wheat proteins.
- the agents according to the invention can be chalk, dicalcium phosphate, insoluble sodium metaphosphate, aluminum silicate, layered silicates, hydrotalcites, calcium pyrophosphate, finely divided synthetic resins, silicas, aluminum oxide, aluminum oxide trihydrate, talc, zeolites, magnesium aluminum silicate (Veegulfat®), magnesium carbonate / Veium sulfate, calcium carbonate or
- auxiliary substances and additives are finally flavor components, for example peppermint oil, spearmint oil, anise oil, stemanis oil, caraway oil, eucalyptus oil, fennel, cinnamon oil, clove oil, geranium oil, sage oil, pi ment oil, thyme oil, marjoram oil, basil oil, citrus oil, Gaultheria oil or one or more components of these oils isolated or synthetically produced therefrom, such as eg menthol, carvone, anethole, cineole, eugenol, cinnamaldehyde, cargophyllene, geraniol, citronellol, linalool, salves, thymol, Terpinan, terpinol, methylchavicol and methyl salicylate.
- peppermint oil spearmint oil, anise oil, stemanis oil, caraway oil, eucalyptus oil, fennel, cinnamon oil, clove oil, geranium
- Suitable flavors are, for example, methyl acetate, vanillin, lonone, linalyl acetate, rhodinol and piperitone.
- Suitable sweeteners are either natural sugars such as sucrose, maltose, lactose and fructose or synthetic sweeteners such as saccharin sodium salt, sodium cyclamate or aspartame.
- humectants such as e.g. Sorbitol or glycerin, consistency regulator, deodorising agents, agents against oral and dental diseases, water-soluble fluorine compounds such as Sodium fluoride or sodium monofluorophosphate.
- auxiliaries and additives are not critical per se and depends on the type of agent that is ultimately to be assembled.
- the proportion will usually be 5 to 98% by weight, preferably 80 to 90% by weight, based on the composition.
- Typical toothpastes which are a further subject of the present invention, generally have the following composition:
- the surfactant mixtures were used in a standard toothpaste formulation.
- the foaming power was determined according to the friction foam method in an EHMEDA friction foam device [greases, soaps, paints. 66, 955 (1964)].
- 20 g of toothpaste were dispersed in 180 g of water and heated to 45 ° C. in the foam cylinder.
- 60 seconds of friction with a vertically rotating Perlon brush at 2600 rpm generated foam on a cylindrically shaped metal wire mesh.
- Table 1 lists the foam volume after 0.5 min and 5 min after the end of foam generation and the drainage water separated from the foam after 5 min.
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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
Description
Claims
Priority Applications (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
EP99969326A EP1113781A1 (de) | 1998-09-17 | 1999-09-08 | Verwendung von monoglycerid(ether)sulfaten und chitosan in mund- und zahnpflegemitteln |
AU59748/99A AU5974899A (en) | 1998-09-17 | 1999-09-08 | Use of monoglyceride (ether) sulfates and chitosan in oral and dental hygiene products |
JP2000573696A JP2002526431A (ja) | 1998-09-17 | 1999-09-08 | 口腔および歯の衛生生成物におけるモノグリセリド(エーテル)スルフェートおよびキトサンの使用 |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE1998142635 DE19842635A1 (de) | 1998-09-17 | 1998-09-17 | Verwendung von Monoglycerid(ether)sulfaten |
DE19842635.6 | 1998-09-17 |
Publications (1)
Publication Number | Publication Date |
---|---|
WO2000016735A1 true WO2000016735A1 (de) | 2000-03-30 |
Family
ID=7881304
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/EP1999/006612 WO2000016735A1 (de) | 1998-09-17 | 1999-09-08 | Verwendung von monoglycerid(ether)sulfaten und chitosan in mund- und zahnpflegemitteln |
Country Status (5)
Country | Link |
---|---|
EP (1) | EP1113781A1 (de) |
JP (1) | JP2002526431A (de) |
AU (1) | AU5974899A (de) |
DE (1) | DE19842635A1 (de) |
WO (1) | WO2000016735A1 (de) |
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2005512992A (ja) * | 2001-11-06 | 2005-05-12 | ペルフェッティ ヴァン メッレ ソシエタ ペル アチオニ | 抗歯石および抗歯垢固形口腔組成物従来技術 |
CN1939255B (zh) * | 2005-09-30 | 2010-04-21 | 姚春阳 | 一种甲壳素牙膏 |
CN103006455A (zh) * | 2011-09-27 | 2013-04-03 | 黄庆禄 | 一种壳聚糖护齿牙膏的配制 |
Families Citing this family (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN104546541A (zh) * | 2015-01-26 | 2015-04-29 | 莫治玲 | 壳聚糖牙膏 |
Citations (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE3343200A1 (de) * | 1982-11-30 | 1984-05-30 | Lion Corp., Tokio / Tokyo | Oralpraeparat |
JPS61151112A (ja) * | 1984-12-25 | 1986-07-09 | Lion Corp | 歯垢形成抑制剤組成物 |
DE4406748A1 (de) * | 1994-03-02 | 1995-09-07 | Henkel Kgaa | Mund- und Zahnpflegemittel |
WO1996016991A1 (de) * | 1994-12-02 | 1996-06-06 | Henkel Kommanditgesellschaft Auf Aktien | Kationische biopolymere |
EP0795316A1 (de) * | 1996-02-14 | 1997-09-17 | Henkel Kommanditgesellschaft auf Aktien | Kosmetisch und/oder pharmazeutische Emulsionen enthaltend Partialglycerid(ether)sulfate, Emulgatoren und Chitosane |
DE19703362C1 (de) * | 1997-01-30 | 1997-11-20 | Henkel Kgaa | Verwendung von Chitosanen und/oder Chitosanderivaten |
-
1998
- 1998-09-17 DE DE1998142635 patent/DE19842635A1/de not_active Ceased
-
1999
- 1999-09-08 AU AU59748/99A patent/AU5974899A/en not_active Abandoned
- 1999-09-08 EP EP99969326A patent/EP1113781A1/de not_active Withdrawn
- 1999-09-08 WO PCT/EP1999/006612 patent/WO2000016735A1/de not_active Application Discontinuation
- 1999-09-08 JP JP2000573696A patent/JP2002526431A/ja active Pending
Patent Citations (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE3343200A1 (de) * | 1982-11-30 | 1984-05-30 | Lion Corp., Tokio / Tokyo | Oralpraeparat |
JPS61151112A (ja) * | 1984-12-25 | 1986-07-09 | Lion Corp | 歯垢形成抑制剤組成物 |
DE4406748A1 (de) * | 1994-03-02 | 1995-09-07 | Henkel Kgaa | Mund- und Zahnpflegemittel |
WO1996016991A1 (de) * | 1994-12-02 | 1996-06-06 | Henkel Kommanditgesellschaft Auf Aktien | Kationische biopolymere |
EP0795316A1 (de) * | 1996-02-14 | 1997-09-17 | Henkel Kommanditgesellschaft auf Aktien | Kosmetisch und/oder pharmazeutische Emulsionen enthaltend Partialglycerid(ether)sulfate, Emulgatoren und Chitosane |
DE19703362C1 (de) * | 1997-01-30 | 1997-11-20 | Henkel Kgaa | Verwendung von Chitosanen und/oder Chitosanderivaten |
Non-Patent Citations (1)
Title |
---|
PATENT ABSTRACTS OF JAPAN vol. 010, no. 350 (C - 387) 26 November 1986 (1986-11-26) * |
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2005512992A (ja) * | 2001-11-06 | 2005-05-12 | ペルフェッティ ヴァン メッレ ソシエタ ペル アチオニ | 抗歯石および抗歯垢固形口腔組成物従来技術 |
CN1939255B (zh) * | 2005-09-30 | 2010-04-21 | 姚春阳 | 一种甲壳素牙膏 |
CN103006455A (zh) * | 2011-09-27 | 2013-04-03 | 黄庆禄 | 一种壳聚糖护齿牙膏的配制 |
Also Published As
Publication number | Publication date |
---|---|
EP1113781A1 (de) | 2001-07-11 |
AU5974899A (en) | 2000-04-10 |
DE19842635A1 (de) | 2000-05-11 |
JP2002526431A (ja) | 2002-08-20 |
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