EP0029805B1 - Barre de savon avec un effet antimicrobien et procédé pour la réduction de son changement de couleur - Google Patents

Barre de savon avec un effet antimicrobien et procédé pour la réduction de son changement de couleur Download PDF

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Publication number
EP0029805B1
EP0029805B1 EP80810343A EP80810343A EP0029805B1 EP 0029805 B1 EP0029805 B1 EP 0029805B1 EP 80810343 A EP80810343 A EP 80810343A EP 80810343 A EP80810343 A EP 80810343A EP 0029805 B1 EP0029805 B1 EP 0029805B1
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Prior art keywords
weight
soap bar
soap
silicate
total weight
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Expired
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EP80810343A
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German (de)
English (en)
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EP0029805A1 (fr
Inventor
Boris Moesch
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Novartis AG
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Ciba Geigy AG
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Classifications

    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
    • C11D3/48—Medical, disinfecting agents, disinfecting, antibacterial, germicidal or antimicrobial compositions
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D9/00—Compositions of detergents based essentially on soap
    • C11D9/04—Compositions of detergents based essentially on soap containing compounding ingredients other than soaps
    • C11D9/06—Inorganic compounds
    • C11D9/18—Water-insoluble compounds

Definitions

  • the present invention relates Seifenstük- ⁇ e ung with antimicrobial activity and a method for reducing the induced by the anti-microbial agent discolouration J of the soap or to improve the aspect of the said soap.
  • Halogenated phenols are known as antimicrobial agents, which can also be incorporated into soaps, e.g. to give a disinfectant effect.
  • Many such phenolic compounds, e.g. Halogenated o-hydroxydiphenyl ethers, which are excellent antimicrobial agents and therefore also achieve excellent effects in soaps see e.g. GB-A-1 024022), have the disadvantage that they yellow the soap bars when they are exposed to the light. In this way there is an undesirable unsightly aspect of the soap bars.
  • the aim of the present invention is to solve the aforementioned problem. It was surprisingly found that the addition of practically water-insoluble, non-colored silicates to the soap composition is particularly effective in reducing the discoloration of the soap under the action of light, and to a much greater extent than the known methods described above can achieve.
  • the soap bar according to the invention with an antimicrobial effect which is a halogenated o-hydroxydiphenyl ether of the formula wherein X is halogen, methyl, methoxy or hydroxy, Y is hydrogen, methyl or trifluoromethyl, Hal is a halogen atom and m is the number 0, 1 or 2, as an antimicrobial active ingredient, is characterized in that it additionally contains a practically water-insoluble, non-colored silicate contains.
  • Preferred antimicrobial active ingredients in soap bars according to the invention correspond to the formula wherein Hal and Hah each independently represent a halogen atom and Y 1 is hydrogen or halogen.
  • Halogens in formulas (1) and (2) are fluorine, chlorine, bromine and iodine, in particular chlorine and bromine, preferably chlorine.
  • antibacterial compounds of the formula (1) or (2) which may be mentioned, for example: 3 ', 4,4' trichloro-2-hydroxy diphenyl ether, 4,4'-dichloro-2-hydroxy diphenyl ether, 4-chloro-4'-bromo -2-hydroxydiphenyl ether, 4-chloro-4'-iodo-2-hydroxydiphenyl ether, 4-chloro-4 '-fluoro-2-hydroxydiphenyl ether, 4-bromo-4'-chloro-2-hydroxydiphenyl ether, 4-bromo-2' , 4'-dichloro-2-hydroxydiphenyl ether, 4,4'-dibromo-2-hydroxydiphenyl ether, 4,2'-4'-trichloro-2-hydroxydiphenyl ether and 4,4 ' , 5 ' trichloro-2-hydroxy-diphenyl ether .
  • the antimicrobial compounds of the formula (1) can also be used together with other antimicrobial compounds, such as halogenated hydroxydiphenylmethanes, halogenated salicylanilides, halogenated diphenylureas, such as trichlorocarbanilide, tribromosalicylanilide, dibromosalicylanilide and the zinc salt of 1-hydroxy-2-ene-pyridene in pyrid be included.
  • other antimicrobial compounds such as halogenated hydroxydiphenylmethanes, halogenated salicylanilides, halogenated diphenylureas, such as trichlorocarbanilide, tribromosalicylanilide, dibromosalicylanilide and the zinc salt of 1-hydroxy-2-ene-pyridene in pyrid be included.
  • Particularly preferred soap bars according to the invention contain 4,2 ', 4'-trichloro-2-hydroxydiphenyl ether as the antimicrobial compound.
  • the soap bars according to the invention generally contain the antimicrobial active substance (or mixtures of several antimicrobially active substances) in a concentration of 0.05 to 3, preferably 0.2 to 2% by weight, based on the total weight of the soap bar.
  • Suitable cations for the above-mentioned silicate structures are all those which do not color the silicates formed with them and do not make them water-soluble.
  • divalent ions come into consideration, in particular alkaline earth metal ions such as Ca, Mg, Ba. Magnesium silicates are particularly preferred.
  • mixed silicates with several cations can also be used, e.g. with Na, K, AI etc., as well as mixed salts with other anions (e.g. OH-, CI-, F- etc.).
  • Silicon atoms in polymeric silicate anions can also be partially replaced by aluminum or other atoms which can usually replace silicon in such compounds.
  • Silicates in question can also be characterized by a certain ratio between the corresponding metal oxide and Si0 2 , for example according to the hypothetical formula where Kat is a cation as defined above, n, x and y are specific numbers, for example n and x numbers between 0.5 and 1.5 and y numbers between 0.6 and 6.
  • These silicates can also contain further metal atoms, for example in the form of oxides MeO or Me 2 0 3 , in which Me means, for example, boron, beryllium, aluminum and similar metal atoms.
  • magnesium silicates for example those of the formula, are preferably used as silicates in the soap bars according to the invention wherein y 'is any number between 1 and 3.5, preferably between 1 and 1.5.
  • y ' is any number between 1 and 3.5, preferably between 1 and 1.5.
  • MgO: Sl02 is 1: 3.5 to 1: 1, in particular 1: 1.5 to 1: 1.
  • the magnesium silicate has the formula MgSi0 3 .
  • a soap bar according to the invention preferably contains 0.1 to 10, in particular 0.5 to 5% by weight of silicate, based on the total weight of the soap bar.
  • soap bar according to the invention does not consist anyway of a so-called “over-greased soap", that is to say from a soap which still contains free, in particular straight-chain, preferably largely saturated fatty acids with 8-22 carbon atoms, such acids can additionally be incorporated into the soap base will.
  • the soap bars according to the invention can then additionally preferably contain about 0.1 to 15, in particular 1 to 10% by weight of free fatty acids, based on the total weight of the soap bar.
  • the additional presence of the free fatty acids can further improve the improvement of the aspect of the soap bar achieved by the silicate (by reducing the discoloration in the light). An effect is then achieved which is better than that caused by the silicate alone, and which is of course significantly better than that which would have resulted from the free fatty acids alone (see example part).
  • fatty acids with 8-22 carbon atoms which may be present in soap bars according to the invention (also mixtures thereof), include: caprin, lauric, myristic, palmitic, stearic, arachine, sebacic, dodecanedi -, Thapsis, Hexadecandi- and Octadecandicarbonklare and mixtures of acids obtained from coconut oil, tallow fat or palm kernel oil.
  • caprin lauric
  • myristic, palmitic, stearic, arachine sebacic
  • dodecanedi -, Thapsis Hexadecandi- and Octadecandicarbonklare
  • Stearic acid, palmitic acid, myristic acid, lauric acid and the acid mixtures obtained from coconut oil, tallow fat and palm kernel oils are preferred.
  • N-acylsarcosine derivatives can bring about a further improvement in the aspect or a reduction in discoloration.
  • compounds of the formula are preferred wherein R is alkyl or alkenyl having 8 to 17 carbon atoms. Examples of such compounds are N-lauryl sarcosine and N-oleoyl sarcosine.
  • the sarcosine derivatives mentioned are preferably present in the soap bars according to the invention in an amount of 1 to 15% by weight, preferably 1 to 5% by weight, based on the total weight of the soap bar. They can be contained in the soap bars either alone (together with a silicate, of course) or together with the fatty acids mentioned above.
  • the soap bars according to the invention are produced as usual.
  • the basic soap is an antibacterial active ingredient of the formula (1) (or mixtures of active ingredients) with the silicate and optionally with a fatty acid or a mixture of fatty acids each with 8-22 carbon atoms (provided the basic soap does not already contain free fatty acids) or / and additionally incorporated with the previously mentioned N-acyl sarcosines.
  • soap base other constituents customary in soaps can be incorporated into the soap base, such as matting agents, for example Ti0 2 , and complexing agents and water softeners, for example complexones such as NTA, EDTA, DTPA, perfumes and others
  • the basic soap used can be, for example, soaps which are obtained by saponification of certain mixtures of different fats (triglycerides).
  • fats triglycerides
  • examples of such fats are: tallow fat, sperm oil, coconut oil, palm kernel oil, ricinus oil, lard, olive oil etc.
  • the soaps can also be prepared from the corresponding acids by neutralization, e.g. from a mixture of tallow fatty acid, coconut palm kernel oil fatty acid and olein.
  • the present invention also relates to a process for improving the aspect of soaps which contain one or more halogenated o-hydroxydiphenyl ethers of the formula (1) as antimicrobial active ingredient, or a process for reducing the discoloration of soaps in light, especially in sunlight, which discoloration is caused by the halogenated o-hydroxydiphenyl ether of the formula (1) added to the soap as antimicrobial active substances.
  • This process according to the invention is characterized in that a practically water-insoluble, non-colored silicate is added to the soap base and intimately mixed therein. The more detailed specification of the silicates added in the process according to the invention can be found in the above description of the soap bars which can be produced therewith.
  • silicate based on the total weight of the finished soap, is preferably added to the soap base.
  • alkaline earth metal silicates preferably calcium or magnesium silicates, in particular magnesium silicates.
  • free, in particular straight-chain, preferably largely saturated fatty acids having 8-22 carbon atoms or mixtures of such fatty acids can also be added to the soap composition, preferably in an amount of 0 , 1 to 15, in particular 1 to 10 wt .-%, based on the total weight of the finished soap.
  • fatty acids examples include: capric, lauric, myristic, palmitic, stearic, arachine, sebacic, dodecanedio, thapsis, hexadecanedio and octadecanedicarboxylic acids and mixtures of acids obtained from coconut oil, tallow fat or palm kernel oil.
  • capric, lauric, myristic, palmitic, stearic, arachine, sebacic dodecanedio, thapsis, hexadecanedio and octadecanedicarboxylic acids and mixtures of acids obtained from coconut oil, tallow fat or palm kernel oil.
  • Stearic acid, palmitic acid, myristic acid, lauric acid and the acid mixtures obtained from coconut oil, tallow fat and palm kernel oils are preferred.
  • N-acylsarcosine derivatives in particular those of the formula, can also be used to further improve the aspect of the soap bars according to the invention of the basic soap composition where R is alkyl or alkenyl having 8 to 17 carbon atoms, add.
  • These sarcosine derivatives can be incorporated into the basic soap composition in an amount of 1 to 15% by weight, preferably 1 to 5% by weight, based on the total weight of the bar of soap.
  • a variant of the process according to the invention consists in that the base soap is not directly incorporated with a practically water-insoluble silicate, but instead a mixture of a water-soluble silicate, such as, for example, an alkali metal silicate, such as water glass, and a metal salt is added, which with the water-soluble silicate forms a practical one water-insoluble silicate reacts.
  • the metal salt can of course only be one which, together with the water-soluble silicate, forms a practically insoluble, non-coloring silicate in water.
  • Non-colored salts of divalent or trivalent cations, in particular alkaline earth metal salts, for example salts of calcium and especially magnesium, are suitable.
  • the nature of the anion of these salts is of minor importance. For example, it can be a hydroxyl, halide, sulfate, nitrate or acetate ion or another anion of an inorganic or organic acid, which forms a preferably readily water-soluble salt with the metal.
  • Parts in each case mean parts by weight, percentages percentages by weight.
  • the additives shown in Table 1 below are added to a base soap mass obtained by saponification of a composition consisting of 75% tallow fat, 20% coconut fat and 5% lard. In this way, the soap patterns A, B and C are formed, the composition of which can also be found in Table 1.
  • the 3 soap samples are now exposed to daylight to check the light stability or to determine the degree of discoloration, namely up to 112, 505, 1471 and 1750 Langley.
  • the degree of whiteness (brightness value) of the samples was then measured using a Zeiss ®Elrepho photometer (standard illuminant D65, 2 degree normal observer, filter FL 40), expressed in%, based on the absolute white in accordance with the CIE recommendation of 1.1.1969 .
  • the whiteness values (brightness values) obtained are given in Table 2 below (in%) (WG).
  • the table also shows the differences (reduction) in the whiteness values (brightness values) compared to the respective unexposed pattern ( ⁇ Y).
  • Table 2 clearly shows that the whiteness (brightness) reduction (AY) caused by the addition of 4,2 ', 4'-trichloro-2-hydroxydiphenyl ether is significantly reduced or the whiteness is significantly increased by the addition of 1% MgSiOa .
  • the additives shown in Table 3 below are added to a base soap composition obtained by saponification of a composition consisting of 75% tallow fat, 20% coconut fat and 5% lard. In this way, the soap patterns B 1 to B 10 are formed, the composition of which can also be found in Table 3.
  • the soap samples are now exposed to daylight to check the light stability or to determine the degree of discoloration, namely up to 150, 500 and 1000 Langley. Then the degree of whiteness (brightness value) of the samples is measured using a Zeiss ®Elrepho photometer (standard illuminant D65, 2 degree normal observer, filter FL 40), expressed in%, based on the absolute white in accordance with the CIE recommendation of 1.1.1969 .
  • the whiteness values (brightness values) obtained are given in Table 4 below (in%) (WG).
  • the table also shows the differences (reduction) in the whiteness values (brightness values) compared to the respective unexposed pattern ( ⁇ Y)
  • Table 4 clearly shows that the whiteness (brightness) reduction (AY) caused by the addition of 4,2 ', 4'-trichloro-2-hydroxydiphenyl ether by the addition of 1% or 2% MgSi0 3 (sample B3, B4) significantly reduced or the degree of whiteness is significantly increased.
  • a further increase in the degree of whiteness (reduction in the loss of brightness) is achieved by the additional use of stearic acid (samples B 5, B 6) and / or lauroylsarcosine (samples B 7-B 10).

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  • Chemical & Material Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Wood Science & Technology (AREA)
  • Organic Chemistry (AREA)
  • Inorganic Chemistry (AREA)
  • Detergent Compositions (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)

Claims (13)

1. Pain de savon à effet anti-microbien, contenant un o-hydroxydiphényléther halogéné de formule:
Figure imgb0019
où X est un halogène, un groupe méthyle, mé- thoxy ou hydroxyle; Y est de l'hydrogène, un groupe méthyle ou trifluorométhyle; Hal est un atome d'halogène, et m est le nombre 0, 1 ou 2, comme matière active anti-microbienne, caractérisé par le fait qu'il contient en supplément un silicate non coloré, pratiquement insoluble dans l'eau.
2. Pain de savon selon la revendication 1, qui contient comme matière active anti-microbienne un o-hydroxydiphényléther halogéné de formule:
Figure imgb0020
où Hal et Hall représentent à chaque fois indépendamment l'un de l'autre un atome d'halogène, et Y1 est de l'hydrogène ou un halogène, de préférence le 4,2',4'-trichtoro-2-hydroxydiphényléther.
3. Pain de savon selon les revendications 1 ou 2, qui contient la matière active anti-microbienne en une concentration de 0,05 à 3%, de préférence de 0,2 à 2% en poids calculés sur le poids total du pain de savon.
4. Pain de savon selon la revendication 1, caractérisé par le fait qu'il contient le silicate en une concentration de 0,1 à 10, de préférence de 0,5 à 5% en poids, rapportés au poids total du pain de savon.
5. Pain de savon selon l'une quelconque des revendications 1 à 4, caractérisé par le fait qu'il contient un silicate de métal alcalino-terreux pratiquement insoluble dans l'eau, en particulier un silicate de magnésium.
6. Pain de savon selon la revendication 1, caractérisé par le fait qu'il contient en supplément un ou plusieurs acide(s) gras libre(s), de préférence largement saturé(s), ayant à chaque fois de 8 à 22 atomes de carbone, en particulier en une concentration de 0,1 à 15, surtout de 1 à 10% en poids, rapportés au poids total du pain de savon.
7. Pain de savon selon la revendication 6, caractérisé par le fait qu'il contient comme acide gras, l'acide stéarique, l'acide laurique, l'acide palmitique, l'acide myristique ou des mélanges d'acides qui peuvent être obtenus à partir de l'huile de coprah, de la stéarine ou des huiles de palme, mais de préférence l'acide stéarique.
8. Pain de savon selon l'une quelconque des revendications 1 à 7, caractérisé par le fait qu'il contient en supplément une N-acylsarcosine; de préférence une ayant la formule:
Figure imgb0021
où R est un groupe alkyle ou alcényle avec 8 à 17 atomes de carbone, et, précisément, de préférence en une concentration de 1 à 15, en particulier de 1 à 5% en poids, rapportés au poids total du pain de savon.
9. Pain de savon selon l'une quelconque des revendications 1 à 8, caractérisé par le fait qu'il contient encore des additifs usuels des savons, par exemple des parfums, des produits de matage, des colorants, des complexants et des adoucisseurs pour l'eau.
10. Procédé pour diminuer le changement de couleur des savons, provoqué par l'addition d'o-hydroxydiphényléthers halogénés de formule (1), efficaces comme anti-microbiens, caractérisé par le fait qu'on ajoute au savon de base un silicate non coloré, pratiquement insoluble dans l'eau, puis qu'on mélange le tout intimement.
11. Procédé selon la revendication 10, caractérisé par le fait qu'on ajoute de 0,1 à 10, de préférence de 0,5 à 5% en poids de silicate, rapportés au poids total du savon terminé.
12. Procédé selon les revendications 10 ou 11, caractérisé par le fait qu'on ajoute un silicate de métal alcalino-terreux, de préférence un silicate de magnésium.
13. Procédé selon la revendication 10, caractérisé par le fait que, en vue de diminuer davantage le changement de couleur, on incorpore en supplément dans le savon de base, un acide gras libre, de préférence largement saturé, ayant de 8 à 22 atomes de carbone, ou un mélange de plusieurs de ces acides gras, et, précisément, de préférence en une quantité de 0,1 à 15, en particulier de 1 à 10% en poids, rapportés au poids total du savon terminé.
EP80810343A 1979-11-16 1980-11-10 Barre de savon avec un effet antimicrobien et procédé pour la réduction de son changement de couleur Expired EP0029805B1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH1025379 1979-11-16
CH10253/79 1979-11-16

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EP0029805A1 EP0029805A1 (fr) 1981-06-03
EP0029805B1 true EP0029805B1 (fr) 1982-10-20

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US (1) US4326978A (fr)
EP (1) EP0029805B1 (fr)
JP (1) JPS5684799A (fr)
AU (1) AU6441380A (fr)
BR (1) BR8007455A (fr)
DE (1) DE3060975D1 (fr)
ES (1) ES496894A0 (fr)
ZA (1) ZA807081B (fr)

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US4773936A (en) * 1985-06-24 1988-09-27 The Dow Chemical Company Insoluble pigments and preparation thereof
US4769080A (en) * 1985-06-24 1988-09-06 The Dow Chemical Company Insoluble pigments and preparation thereof
US4840676A (en) * 1985-06-24 1989-06-20 The Dow Chemical Company Insoluble pigments and preparation thereof
US4929381A (en) * 1985-06-24 1990-05-29 The Dow Chemical Company Inorganic anion exchangers and preparation thereof
US4769079A (en) * 1985-06-24 1988-09-06 The Dow Chemical Company Insoluble pigments and preparation thereof
US4655794A (en) * 1986-03-20 1987-04-07 Sybron Chemicals Holdings Inc. Liquid cleaner containing viable microorganisms
US4832861A (en) * 1988-05-27 1989-05-23 Lever Brothers Company Soap compositions of enhanced antimicrobial effectiveness
US5006529A (en) * 1988-05-27 1991-04-09 Lever Brothers Company Soap compositions of enhanced antimicrobial effectiveness
US4954281A (en) * 1988-05-27 1990-09-04 Lever Brothers Company Soap compositions of enhanced antimicrobial effectiveness
ZA921779B (en) * 1991-03-18 1992-11-25 Grace W R & Co A process for producing a synthetic detergent soap base from n-acyl sarcosine
GB9623377D0 (en) * 1996-11-09 1997-01-08 Reckitt & Colmann Prod Ltd Organic compositions
GB0410968D0 (en) * 2004-05-17 2004-06-16 Greenbridge Environmental Cont Skin cleaning composition
DE102008004890A1 (de) * 2008-01-17 2009-07-23 Lanxess Deutschland Gmbh Verfahren zur Einarbeitung antimikrobieller Produkte in Seifenmassen

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AU6441380A (en) 1981-05-21
JPS5684799A (en) 1981-07-10
BR8007455A (pt) 1981-05-26
ZA807081B (en) 1981-11-25
ES8308355A1 (es) 1982-12-16
EP0029805A1 (fr) 1981-06-03
US4326978A (en) 1982-04-27
DE3060975D1 (en) 1982-11-25
ES496894A0 (es) 1982-12-16

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