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WO2001010998A1 - Savons a base de detergents synthetiques - Google Patents

Savons a base de detergents synthetiques Download PDF

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Publication number
WO2001010998A1
WO2001010998A1 PCT/EP2000/007331 EP0007331W WO0110998A1 WO 2001010998 A1 WO2001010998 A1 WO 2001010998A1 EP 0007331 W EP0007331 W EP 0007331W WO 0110998 A1 WO0110998 A1 WO 0110998A1
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WIPO (PCT)
Prior art keywords
acid
alkyl
carbon atoms
fatty acid
fatty
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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PCT/EP2000/007331
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German (de)
English (en)
Inventor
Hermann Hensen
Anke Eggers
Werner Seipel
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BASF Personal Care and Nutrition GmbH
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Cognis Deutschland GmbH and Co KG
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Publication of WO2001010998A1 publication Critical patent/WO2001010998A1/fr
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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
    • C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
    • C11D1/66—Non-ionic compounds
    • C11D1/74—Carboxylates or sulfonates esters of polyoxyalkylene glycols
    • 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
    • C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
    • C11D1/66—Non-ionic compounds
    • C11D1/825—Mixtures of compounds all of which are non-ionic
    • 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
    • C11D17/00—Detergent materials or soaps characterised by their shape or physical properties
    • C11D17/0047—Detergents in the form of bars or tablets
    • C11D17/006—Detergents in the form of bars or tablets containing mainly surfactants, but no builders, e.g. syndet bar
    • 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
    • C11D3/16—Organic compounds
    • C11D3/20—Organic compounds containing oxygen
    • C11D3/22—Carbohydrates or derivatives thereof
    • C11D3/222—Natural or synthetic polysaccharides, e.g. cellulose, starch, gum, alginic acid or cyclodextrin
    • 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
    • C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
    • C11D1/02—Anionic compounds
    • C11D1/12—Sulfonic acids or sulfuric acid esters; Salts thereof
    • C11D1/123—Sulfonic acids or sulfuric acid esters; Salts thereof derived from carboxylic acids, e.g. sulfosuccinates
    • 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
    • C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
    • C11D1/02—Anionic compounds
    • C11D1/12—Sulfonic acids or sulfuric acid esters; Salts thereof
    • C11D1/126—Acylisethionates
    • 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
    • C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
    • C11D1/02—Anionic compounds
    • C11D1/12—Sulfonic acids or sulfuric acid esters; Salts thereof
    • C11D1/14—Sulfonic acids or sulfuric acid esters; Salts thereof derived from aliphatic hydrocarbons or mono-alcohols
    • C11D1/143—Sulfonic acid esters
    • 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
    • C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
    • C11D1/02—Anionic compounds
    • C11D1/12—Sulfonic acids or sulfuric acid esters; Salts thereof
    • C11D1/29—Sulfates of polyoxyalkylene ethers
    • 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
    • C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
    • C11D1/38—Cationic compounds
    • C11D1/52—Carboxylic amides, alkylolamides or imides or their condensation products with alkylene oxides
    • C11D1/525—Carboxylic amides (R1-CO-NR2R3), where R1, R2 or R3 contain two or more hydroxy groups per alkyl group, e.g. R3 being a reducing sugar rest
    • 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
    • C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
    • C11D1/66—Non-ionic compounds
    • C11D1/662—Carbohydrates or derivatives
    • 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
    • C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
    • C11D1/88—Ampholytes; Electroneutral compounds
    • C11D1/90—Betaines

Definitions

  • the invention relates to fatty acid-free syndet soaps containing alkoxylated carboxylic acids and starches
  • Stucco soaps play a major role in body cleansing, which are now produced on an industrial scale by continuous saponification of free fatty acids with alkalis, concentrates of basic soaps and spray drying.
  • the so-called “syndetbars” have a special status. They are free of fatty acid salts except for impurities and contain only synthetic surfactants
  • the soap sticks obtainable according to the teaching of the prior art do not always develop a sufficient amount of foam, and also foam consistency and, in particular, the feeling on the skin can be desired. If free fatty acids are used as releasing agents, corrosion problems can also arise in the production plants
  • the object of the invention was then to provide syndet soaps which are free from the disadvantages described.
  • new stucco soap compositions must also be able to be produced on an industrial scale, ie that the compositions have, for example, sufficient but not too high deformability possess and do not tend to crack during drying
  • the invention relates to syndet soaps containing
  • R 1 CO stands for an aliphatic acyl radical having 6 to 30 C atoms
  • AlkO for alkylene oxide
  • n for numbers from 1 to 30
  • R 2 for an aliphatic alkyl radical with 1 to 8 carbon atoms
  • stucco soaps with improved foam capacity and optimized skin feel can be produced in the absence of fatty acids or fatty acid salts if alkoxylated carboxylic acids are used as the main surfactant component, preferably in anhydrous form, and strong starch is used.
  • the invention includes the knowledge that the mixtures are also outstandingly suitable for the large-scale production of syndet soaps, ie they are stable when stored in the air, are not hygrospopical, deformable, but not too hard, and do not show any cracking during drying.
  • Alkoxylated carboxylic acid esters which form component (a) are known from the prior art.
  • such alkoxylated carboxylic acid esters can be obtained by etherification of al carboxylated carboxylic acids accessible with alcohols.
  • the compounds are preferably prepared by reacting carboxylic acid esters with alkylene oxides using catalysts, in particular using calcined hydrotalcite according to German Offenlegungsschrift DE 3914131 A, which provide compounds with a restricted homolog distribution.
  • Both carboxylic acid esters of monohydric alcohols and polyhydric alcohols can be alkoxylated by this process.
  • alkoxylated carboxylic acid esters of the formula (I) are preferably used
  • R 1 CO stands for an aliphatic acyl radical with 6 to 30 C atoms
  • AlkO for alkylene oxide
  • n for numbers from 1 to 30
  • R 2 for an aliphatic alkyl radical with 1 to 8 carbon atoms.
  • AlkO stands for the alkylene oxides which are reacted with the carboxylic acid esters and include ethylene oxide, propylene oxide and / or butylene oxide, preferably ethylene oxide and / or propylene oxide, in particular ethylene oxide alone.
  • Preferred acyl radicals are derived from carboxylic acids having 6 to 22 carbon atoms of natural or synthetic origin, in particular from linear, saturated and / or unsaturated fatty acids, including technical mixtures thereof, as are obtainable by fat cleavage from animal and / or vegetable fats and oils, for example from coconut oil, palm kernel oil, palm oil, soybean oil, sunflower oil, rape oil, cottonseed oil, fish oil, beef tallow and lard.
  • carboxylic acids examples include caproic acid, caprylic acid, 2-ethylhexanoic acid, capric acid, lauric acid, isotridecanoic acid, myristic acid, palmitic acid, palmitoleic acid, stearic acid, isostearic acid, oleic acid, elaidic acid, petroselinic acid, linoleic acid, linolenic acid, elaeostearic acid, arachidic acid, gadoleic acid, behenic acid and / or erucic acid.
  • R 1 CO is a linear or branched, aliphatic, saturated and / or unsaturated acyl radical having 10 to 18 carbon atoms
  • AlkO for ethylene oxide and / or propylene oxide, preferably ethylene oxide
  • n for numbers from 5 to 20
  • R 2 represents a methyl radical.
  • examples of such compounds are methyl lauric acid, methyl coconut fatty acid and methyl tallow fatty acid alkoxylated with an average of 5, 7, 9 or 11 moles of ethylene oxide.
  • Untreated starch has the advantage that it is present in the bar soaps in the form of small, solid grains which, when used, have a gentle abrasive effect and improve the feeling on the skin. Hydrolyzed starch leads to products with better deformability and homogeneity.
  • compounds are prepared from alkoxylated carboxylic acids and starch by subjecting aqueous slurries of the two components to drying with superheated steam.
  • Alkyl and alkenyl oligoglycosides which may be included as optional surfactants, are known nonionic surfactants which follow the formula (II)
  • R 3 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.
  • 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 alkenyioligoglucosides.
  • alkyl and / or alkenyl oligoglycosides whose degree of oligomerization is less than 1.7 and in particular between 1.2 and 1.4.
  • the alkyl or alkenyl radical R 3 can be derived from primary alcohols having 4 to 11, preferably 8 to 10, carbon atoms. Typical examples are butanol, capronic alcohol, caprylic alcohol, capric alcohol and undecyl alcohol and their technical mixtures, such as, for example can be obtained 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 3 can also be derived from primary alcohols having 12 to 22, preferably 12 to 14 carbon atoms.
  • Typical examples are lauryl alcohol, mystyl alcohol, cetyl alcohol, palmoleyl alcohol, stearyl alcohol, isostearyl alcohol, oleyl alcohol, elaidyl alcohol, petroselinyl alcohol, gadachyl alcohol, arachyl alcohol Behenyl alcohol, erucyial alcohol, brassidyl alcohol and their technical mixtures, which can be obtained as described above.
  • Alkyl oligoglucosides based on hardened Ci ⁇ m coconut alcohol with a DP of 1 to 3 are preferred.
  • Fatty acid N-alkylpolyhydroxyalkylamides which may also be included as optional surfactants, are nonionic surfactants which follow the formula (III)
  • R 5 CO for an aliphatic acyl radical with 6 to 22 carbon atoms
  • R 4 for an alkyl or hydroxyalkyl radical with 1 to 4 carbon atoms
  • [Z] for a linear or branched polyhydroxyalkyl radical with 3 to 12 carbon atoms and 3 to 10 hydroxyl groups stands.
  • the fatty acid N-alkyl polyhydroxyalkylamides are known substances which can usually be obtained by reductive amination of a reducing sugar with ammonia, an alkylamine or an alkanolamine and subsequent acylation with a fatty acid, a fatty acid alkyl ester or a fatty acid chloride. With regard to the processes for their production, reference is made to US Pat. Nos.
  • the fatty acid N-alkylpolyhydroxyalkylamides are preferably derived from reducing sugars having 5 or 6 carbon atoms, in particular from glucose.
  • the preferred fatty acid N-alkyl polyhydroxyalkylamides are therefore fatty acid N-alkylglucamides, as represented by the formula (IV):
  • fatty acid-N-alkylpolyhydroxyalkylamides are glucamides of the formula (IV) in which R 4 is methyl and R 5 CO is the acyl radical of caproic acid, caprylic acid, capric acid, lauric acid, mypic acid palmitic acid, palmoleic acid, stearic acid, stearic acid, stearic acid, Oleic acid, elaidic acid, petroselinic acid, linoleic acid, linolenic acid, arachic acid, gadolinic acid, behenic acid or erucic acid or their technical mixtures are particularly preferred.
  • R 4 is methyl
  • R 5 CO is the acyl radical of caproic acid, caprylic acid, capric acid, lauric acid, mypic acid palmitic acid, palmoleic acid, stearic acid, stearic acid, stearic acid, Oleic acid, elaidic acid, petroselinic acid, lino
  • Fatty acid N-alkylglucamides of the formula (IV) which are obtained by reductive amination of glucose with methylamine and subsequent acylation Lau ⁇ nsaure or Ci2 / i4-coconut fatty acid or a corresponding De ⁇ vat can be obtained.
  • the polyhydroxyalkylamides can also be derived from maltose and palatinose
  • Monoglycid suifates and monoglycid ether sulfates which may also be present as further anionic surfactants, are known substances which can be obtained by the relevant methods of preparative organic chemistry.
  • the preparation of T ⁇ glycidens is usually used, which, if appropriate, after ethoxylation to give the monoglycends are transesterified and subsequently sulfated and neutralized. It is also possible to convert the partial glycides with suitable sulfating agents, preferably gaseous sulfur trioxide or chlorosulfonic acid [cf. EP 0561825 B1, EP 0561999 B1 (Henkel)].
  • the neutralized substances can be subjected to ultrafiltration in order to reduce the electrolyte content to a desired level [DE 4204700 A1 (Henkel)].
  • Overviews of the chemistry of the monoglycid sulfates are described, for example, by AK Biswas et al in J.Am.Oil.Chem.Soc. 37, 171 (1960) and F U Ahmed J.Am.Oil.Chem. Soc. 67, 8 (1990) appeared.
  • the monoglycid (ether) sulfates to be used in the sense of the invention follow the formula (V),
  • R 6 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 for an alkali or alkaline earth metal.
  • Monoglycid (ether) sulfates suitable for the purposes of the invention are the reaction products of launic acid monoglycid, coconut fatty acid monoglycid, palmitic acid monoglycidic, stearic acid monoglycid, olsauremonoglycidic and tallow fatty acid trinulfide trioxide with their ethylene sulfoxide adduct and their sulfur sulfoxide trioxide with their ethylene sulfoxide adduct and their sulfur sulfoxide trichloride with their ethylene sulfoxide trioxide and their sulfur sulfoxide trioxide with their ethylene sulfoxide trioxide and their sulfur sulfoxide trioxide with their ethylene sulfoxide adduct and their sulfur sulfoxide trioxide with their ethylene sulfoxide trioxide and their sulfur sulfoxide trioxide with their ethylene sulfoxide adduct and their sulfur sulfoxide tri
  • Monoglycid sulfates of the formula (V) are preferably used in which R 6 CO for a linear acyl The remainder has 8 to 18 carbon atoms.
  • the monoglycid (ether) sulfates are preferably used as dry granules or powders which can be obtained, for example, by drying aqueous pastes in a flash dryer
  • Betaines which can also be used as representatives of the amphoteric or zwitte ⁇ onic surfactants, are known substances which are predominantly prepared by carboxyalkylation, preferably carboxymethylation, of ammic compounds.
  • the starting materials are preferably condensed with halocarboxylic acids or their salts, in particular with sodium chloroacetate, with per mol Betaine forms a mole of salt.
  • unsaturated carboxylic acids such as acrylic acid, is also possible.
  • betaine and "real" amphoteric surfactants refer to U Ploog's contribution in soap-oil-fat waxes, 198, 373 (1982).
  • R 7 for alkyl and / or alkenyl radicals with 6 to 22 carbon atoms
  • R 8 for hydrogen or alkyl radicals with 1 to 4 carbon atoms
  • R 9 for alkyl radicals with 1 to 4 carbon atoms
  • q for numbers from 1 to 6 and X.
  • an alkali metal and / or alkaline earth metal or ammonium Typical examples are the carboxymethylation products of hexylmethylamine, hexyldimethylamine, octyldimethylamine, methylamine Decyidi-, dodecylmethylamine, dodecyldimethylamine, Dodecylethylmethylamin, Ci2 / i4-Kokosalkyld ⁇ - methylamine, Mynstyldimethylamin, cetyldimethylamine, stearyldimethylamine, Stearylethylmethylamm, oleyldimethylamine , Ci6 / 18-tallow alkydimethylamine and their technical mixtures. Also suitable are carboxyalkylation products of amidoamines which follow the formula (VII),
  • Typical examples are reaction products of fatty acids oleic acid having 6 to 22 carbon atoms, including caproic, caprylic acid Cap ⁇ nsaure, Lau ⁇ nsaure, My ⁇ stinsaure, palmitic acid, palm, Stea ⁇ saure, Isostea ⁇ nsaure oleic acid, elaidic acid, petroselinic acid, ünolsaure linolenic acid, Elaeostea ⁇ nsaure, arachic Gadoleinsaure, behenic acid and erucic acid and technical mixtures thereof, with N, N-D ⁇ methylam ⁇ noethylam ⁇ n, N, N-D ⁇ methylam ⁇ nopropylam
  • Fatty acid polyglycol ester sulfates which may be present as an optional component preferably follow the formula (I),
  • R 1 is C0 for a linear or branched, saturated or unsaturated acyl radical having 6 to 22 carbon atoms, w for numbers of 1 to 3 on average and AO for a CH2CH2O-, CH 2 CH (CH 3 ) 0- and / or CH ( CH 3 ) CH 2 0 radical and X represents an alkali and / or alkaline earth metal, ammonium, alkylammonium, alkanolammonium or glucammonium, are known anionic surfactants and are prepared by sulfation of the corresponding fatty acid polyglycol esters.
  • ethylene oxide, propylene oxide or a mixture thereof - in random or block distribution - is added to the corresponding fatty acids, this reaction being acid-catalyzed, but preferably in the presence of bases, such as, for example, sodium methylate or calcined hydrotalcite, a degree of alkoxylation of 1 desired, the intermediates can also by esterifying the fatty acids with a corresponding The alkylene glycol can be prepared.
  • the sulfation of the fatty acid polyglycol esters can be carried out in a manner known per se with chlorosulfonic acid or preferably gaseous sulfur trioxide, the molar ratio between fatty acid polyglycol ester and sulfating agent being in the range from 1 0.95 to 1 1, 2, preferably 1 1 to 1 1, 1 and the reaction temperature can be 30 to 80 and preferably 50 to 60 ° C. It is also possible to undersulfate the fatty acid polyglycol esters, ie to use significantly less sulfating agents than would be required for a complete stoichiometric reaction.
  • fatty acid polyglycol ester For example, if molar amounts of fatty acid polyglycol ester are used as sulfating agents from 1 0.5 to 1 0.95 mixtures of fatty acid polyglycol ester sulfates and fatty acid polyglycol esters obtained for a whole series of applications are also advantageous. In order to avoid hydrolysis, it is very important to carry out the neutralization at a pH in the range from 5 to 9, preferably 7 to 8.
  • Typical examples of suitable starting materials are the addition products from 1 to 3 Moles of ethylene oxide and / or propylene oxide, but preferably the adducts with 1 mole of ethylene oxide or 1 mole of propylene oxide with caproic acid, caprylic acid, 2-ethylhexanoic acid, capric acid, lauric acid, isotine decanoic acid, mypine acid, palmitic acid, palmoleic acid steanic acid, oleanic acid, isostolic acid, isostene acid , Linolenic acid, Elaeostea ⁇ nsaure, Arachinsaure, Gadoleinsaure, Behensaure and Erucasaure as well as their technical mixtures, which are then sulfated and neutralized as described above.
  • fatty acid polyglycol ester sulfates of formula (I) are used, in which R 1 CO for an acyl residue with 12 to 18 carbon atoms, x for an average of 1 o the 2, AO represents a CH ⁇ CH ⁇ O group and X represents sodium or ammonium, such as, for example, lauric acid + 1 EO-sulfate-sodium salt, lauric acid + 1 EO-sulfate-ammonium salt, coconut fatty acid + 1EO-sulfate-sodium salt, coconut fatty acid +1 EO sulfate ammonium salt, tallow fatty acid + 1 EO sulfate sodium salt, tallow fatty acid + I EO sulfate ammonium salt and mixtures thereof
  • the stucco soaps according to the invention can contain, as an optional component, olefin sulfonates, which are usually obtained by addition of SO 3 to olefins of the formula (III)
  • R 2 and R 13 independently of one another represent H or alkyl radicals having 1 to 20 carbon atoms, with the proviso that R 12 and R 13 together have at least 6 and preferably 10 to 16 carbon atoms
  • olefin sulfonates but preferably ⁇ -olefin sulfonates, can be used, which result when R 12 or R 13 stand for hydrogen.
  • Typical examples of olefin sulfonates used are the sulfonation products which are obtained by treating SO3 with 1, 2-butene, 1 -, 2-, 3-hexene, 1-, 2-, 3-, 4-octene, 1-, 2-, 3-, 4-, 5-decene, 1-, 2-, 3-, 4-, 5-, 6- dodecene, 1-, 2-, 3-, 4-, 5-, 6-, 7-tetradecene, 1-, 2-, 3-, 4-, 5-, 6-, 7-, 8-hexadecene, 1-, 2-, 3-, 4-, 5-, 6-, 7-, 8-, 9-octadecene, 1-, 2-, 3-, 4-, 5-, 6-, 7-, 8-, 9-octadecene, 1-, 2-, 3-, 4-, 5-,
  • the syndet soaps according to the invention can contain non-ionic, anionic, cationic and / or amphoteric or amphoteric surfactants as further optional surfactant additives.
  • anionic surfactants are soaps, alkyl benzene sulfonates, alkane sulfonates, alkyl ether sulfonates, glycerol ether sulfonates, ⁇ -methyl sulfonate sulfonates, ⁇ -methyl sulfonate sulfonates , Fatty alcohol ether sulfates, glycine ether sulfates, fatty acid ether sulfates, hydroxy mixed ether sulfates fatty acid amid (ether) sulfates, mono- and dialkyl sulfosuccinates, mono- and dialkyl sulfosuccinamates, sulphotylglycerols, amide soaps, amide
  • nonionic surfactants contain polyglycol ether chains, they can have a conventional, but preferably a narrow, homolog distribution.
  • cationic surfactants are quaternary ammonium compounds, such as for example the dimethyldistearylammonium chloride, and ester quats, in particular quaternized fatty acid alkanolamine ester salts.
  • amphoteric or zwitt Erionic surfactants are ammopropionates, ammoglycinates, imidazolinium betame and sulfobetaines.
  • Alkyl sulfates, mono and dialkyl sulfosuccinates, alkyl sulfoacetates and / or isothionates are preferably used.
  • the surfactants mentioned are exclusively known compounds. With regard to the structure and preparation of these substances, see the relevant review, for example. Falbe (ed.), “Surfactants in Consumer Products", Springer Verlag, Berlin, 1987, pp. 54-124 or J.Falbe (ed.), "Catalysts, surfactants and mineral oil additives", Thieme Verlag, Stuttgart, 1978, p 123-217 syndet soaps
  • Syndet soaps with a particularly beneficial feeling on the skin and creamy foam contain the ingredients in the following amounts
  • syndet soaps have the following composition
  • fatty acid N-alkylpolyhydroxyalkylamides preferably fatty acid N-al - Kylglucamide
  • monoglycid (ether) sulfates preferably coconut fatty acid monoglycid sulfate, betaines, fatty acid polyglycol ester sulfates and olefin sulfonates, preferably ⁇ -olefin sulfonates, are used
  • fatty alcohols and polyethylene glycol ethers are fatty alcohols and polyethylene glycol ethers.
  • suitable fatty alcohols are lauryl alcohol, mystyl alcohol, cetearyl alcohol, stearyl alcohol and isostearyl alcohol.
  • Suitable polyethylene glycol ethers are those which have an average molecular weight in the range from 5,000 to 20,000 daltons
  • component (a) and, if appropriate, further surfactants are used in anhydrous, granular form, as obtained after drying in a so-called “flash dryer".
  • flash dryer a so-called "flash dryer”.
  • the syndet soaps according to the invention are practically free of free fatty acids or fatty acid salts, that is to say the content of these substances is below 0.5% by weight.
  • the soaps in use provide a surprisingly high amount of a particularly creamy foam and also impart a very pleasant feeling on the skin
  • syndet soaps can also be used as further auxiliaries and additives, mild surfactants (see above), oils, superfatting agents, consistency enhancers, thickeners, polymers, silicone compounds, fats, waxes, lecithins, phospholipids, stabilizers, biogenic agents, film formers, swelling agents, UV Sun protection factors, antioxidants, hydrotropes, insect repellents, solubilizers, perfumes, dyes and the like contain
  • Substances such as, for example, lanolin and lecithin and polyethoxylated or acylated lanolin and lecithin derivatives, polyol fatty acid ester monoglycides and fatty acid alkanolamides can be used as superfatting agents, the latter simultaneously serving as foam stabilizers
  • Possible consistency agents are primarily fatty alcohols or hydroxyfatty alcohols with 12 to 22 and preferably 16 to 18 carbon atoms and also partial glycides, fatty acids or hydroxyfatty acids.
  • Suitable thickeners are, for example, Aerosil types (hydrophilic silicas), polysaccharides, in particular xanthan gum guar guar, agar agar, algmates and tyloses carboxymethyl cellulose and hydroxyethyl cellulose, and also high molecular weight polyethylene glycol mono- and diesters of fatty acid polyacrylates, (e.g.
  • Suitable cationic polymers are, for example, cationic cellulose derivatives, such as, for example, a quaternized hydroxyethyl cellulose, which is available under the name Polymer JR 400® from Amerchol, cationic strong copolymers of diallylammonium salts and acrylamides, quaternized vinylpyrrohdon / vinylidazole polymers such as, for example, Luviquat® (BASF) , Condensation products of polyglycols and amines, quaternized collagen polypeptides, such as, for example, lauryldimonium hydroxypropyl hydrolyzed collagen (Lamequat®L / Grunau), quaternized wheat polypeptides, polyethylene imine, cationic silicone copolymers, such as amidomethicone, copolymers of adipic acid and dimethylaminodehyde hydroxymethyldiamine-hydroxymetaminethyne-hydroxymethylamine-hydroxymethylamine-
  • Suitable silicone compounds are, for example, dimethylpolysiloxanes, methylphenylpolysiloxanes, cychsche silicones and ammo-, fatty acid-, alcohol-, polyether-, epoxy-, fluorine-, glycoside- and / or alkyl-modified silicone compounds, which can be both liquid and resinous at room temperature Simethicones, which are mixtures of dimethicones with an average chain length of 200 to 300 dimethylsiloxane units and hydrogenated silicates, are suitable.
  • Simethicones which are mixtures of dimethicones with an average chain length of 200 to 300 dimethylsiloxane units and hydrogenated silicates
  • fats are glycine, natural waxes such as e.g. Candehllaw wax, carnauba wax, Japanese wax, esparto grass wax, cork wax, guaruma wax, rice germol wax, sugar cane wax, Ou ⁇ cury wax, montan wax, beeswax, shellac wax, walnut, lanolin (wool wax), broom fat, ceresin, ozokent (earth wax), petrolatum, paraffin wax, chemically modified waxes (hard waxes), such as montan ester waxes, sasol waxes, hydrogenated jojoba waxes and synthetic waxes, such as polyalkylene waxes and polyethylene glycol waxes.
  • natural waxes such as e.g. Candehllaw wax, carnauba wax, Japanese wax, esparto grass wax, cork wax, guaruma wax, rice germol wax, sugar cane wax, Ou ⁇ cury wax, montan wax
  • lecithme is understood by the person skilled in the art to mean those glycerophosphides which form from fatty acids, glycines, phosphoric acid and choline by esterification. Lecithms are therefore often referred to in the art as phosphatidylchone (PC) and follow the general formula
  • R typically stands for linear aliphatic hydrocarbon radicals with 15 to 17 carbon atoms and up to 4 cis double bonds.
  • Examples of natural lecithms include the Kepfahne, which are also referred to as phosphatidic acids, and derivatives of 1,2-diacyl-sn-glycine-3 - Represent phosphoric acids
  • phospholipids are usually understood to be mono- and preferably diesters of phosphoric acid with Glyce ⁇ n (Glyce ⁇ nphosphate), which are generally classified as fats.
  • Glyce ⁇ nphosphate Glyce ⁇ nphosphate
  • sphingosines or Sphingo pide are also suitable
  • Metal salts of fatty acids such as magnesium aluminum and / or zinc stearate or - ⁇ cmoleate, can be used as stabilizers
  • Biogenic active substances are, for example, tocopherol tocopherol acetate, tocopheroipalmitate, ascorbic acid, deoxy ⁇ bonucleic acid, retinol, bisabolol, allantom, phytant ⁇ ol, panthenol, AHA acids, amino acids, ceramides, pseudoceramides, essential oils, plant extracts and vitamin complexes
  • Common film formers are, for example, chitosan, microcrystalline chitosan, quaternized chitosan, polyvinylpyrrohdon, vinylpyrrolidone-vinyl acetate copolymers, polymers of the acrylic acid series, quaternary cellulose derivatives, coils, hyaluronic acid or compounds thereof and similar compounds
  • Montmo ⁇ llonite, clay minerals, pemulene and alkyl-modified carbopol types can serve as swelling agents for aqueous phases. Further suitable polymers or swelling agents can be found in the overview by R Lochhead in Cosm.Toil. 108, 95 (1993)
  • UV light protection factors are, for example, organic substances (light protection filters) which are liquid or crystalline at room temperature and which are able to absorb ultraviolet rays and release the absorbed energy in the form of boring radiation, for example heat.
  • U VB filters can be unsuitable or be water-soluble. Examples of olloic substances are
  • 4-amino benzoic acid derivatives preferably 4- (dimethylamino) benzoic acid 2-ethylhexyiester, 4- (dimethylamino) benzoic acid 2-octyl ester and 4- (dimethylamino) benzoic acid amyl ester,
  • esters of cinnamic acid preferably 2-ethylhexyl 4-methoxyz ⁇ mtsaure, 4-methoxyz ⁇ mtsaurepro- pylester, 4-methoxyz ⁇ mtsaure ⁇ soamylester 2-cyano-3,3-phenylz ⁇ mtsaure-2-ethylhexyl ester (octocrylene),
  • esters of sahcyl acid preferably 2-ethylhexyl sahcylate, 4-isopropylbenzylsylate, homomethyl salicylate,
  • benzophenone preferably 2-hydroxy-4-methoxybenzophenone, 2-hydroxy-4-methoxy-4'-methylben ⁇ zophenone, 2,2'-dihydroxy-4-methoxybenzophenone,
  • esters of benzalmalonic acid preferably 4-methoxybenzmalonic acid 2-ethylhexyl ester, T ⁇ azindenvate, such as 2.4 6-Tr ⁇ an ⁇ l ⁇ no- (p-carbo-2'-ethyl-1 '-hexyloxy) -1, 3,5-t ⁇ az ⁇ n and octyl Tna- zon, as described in EP 0818450 A1 or dioctyl Butamido T ⁇ azone (Uvasorb® HEB),
  • Propane-1,3-dione such as 1- (4-tert-butylphenyl) -3- (4'methoxyphenyl) propane-1,3-dione,
  • Typical UV-A filters include, in particular, derivatives of benzoylmethane, such as 1- (4'-tert-butylphenyl) -3- (4'-methoxyphenyl) propane-1, 3-dione, 4-tert-butyl-4 '-methoxyd ⁇ benzoyl- methane (Parsol 1789), 1-phenyl-3- (4'-isopropyiphenyl) propane-1, 3-dion and enamine compounds as described in DE 19712033 A1 (BASF)
  • the UV-A and UV B filters can of course also be used in mixtures.
  • insoluble light-protection pigments namely finely dispersed metal oxides or salts, are also suitable for this purpose.
  • suitable metal oxides are, in particular, zinc oxide and titanium dioxide and, in addition, oxides of iron, zirconium, silicon, manganese , Aluminum and cerium and their mixtures.
  • Silicates (talc), tree sulfate or zinc stearate can be used as salts.
  • the oxides and salts are used in the form of the pigments for skin-care and skin-protecting emulsions and decorative cosmetics.
  • the particles should have an average diameter of less than 100 nm, preferably between 5 and 50 nm and in particular between 15 and 30 nm.
  • the pigments can also be surface-treated, ie hydrophilized or hydrophobicized Typical examples are coated titanium dioxides, such as titanium dioxide T 805 (Degussa) or Eusolex® T2000 (Merck).
  • the most suitable hydrophobic coating agents are silicones and especially talkoxyoxyctylsilanes or simethicones. So-called micro- or nanopigments are used t Micronized zinc oxide is preferably used. Further suitable UV light protection filters can be found in the overview by P Finkel in S ⁇ FW-Journal 122, 543 (1996)
  • secondary light stabilizers of the antioxidant type can also be used, which interrupt the photochemical reaction chain which is triggered when UV radiation reaches the skin.
  • Typical examples for this are amino acids (e.g. glycine, histidine, tyrosine, tryptophan) and their derivatives, imidazoles (e.g. urocanic acid) and their derivatives, peptides such as D, L-carnosine, D-camosine, L-camosine and their derivatives (e.g. anserine), carotenoids , Carotenes (e.g.
  • ⁇ -carotene, ⁇ -carotene, lycopene and their derivatives, chlorogenic acid and their derivatives, lipoic acid and their derivatives (e.g. dihydroliponic acid), aurothioglucose, propylthiouracil and other thiols (e.g.
  • thioredoxin glutathione, cysteine, cystine, Cystamine and their glycosyl, N-acetyl, methyl, ethyl, propyl, amyl, butyl and lauryl, palmitoyl, oleyl, ⁇ -linoleyl, cholesteryl and glyceryl esters) and their salts, dilauryl thiodipropio ⁇ at , Distearyl thiodipropionate, thiodipropionic acid and their derivatives (esters, ethers, peptides, lipids, nucleotides, nucleosides and salts) as well as sulfoximine compounds (eg buthioninsulfoximines, homocysteine sulfoximine, Butioninsulfone, penta-, hexa-, heptathioninsulfoximine) in very low tolerable do solutions (eg pmol to ⁇ mol
  • Ferulic acid Furfurylidenglucitol, carnosine, butylhydroxytoluene, butylhydroxyanisole, Nordihydroguajak- resin acid, nordihydroguaiaretic acid, trihydroxybutyrophenone, uric acid and derivatives thereof, mannose and derivatives thereof, superoxide dismutase, zinc and derivatives thereof (for example ZnO, ZnS0 4), selenium and derivatives thereof (eg selenium-methionine), stilbenes and their derivatives (eg stilbene oxide, trans-stilbene oxide) and the derivatives (salts, esters, ethers, sugars, nucleotides, nucleosides, peptides and lipids) of these active substances which are suitable according to the invention.
  • ZnO, ZnS0 4 zinc and derivatives thereof
  • selenium and derivatives thereof eg selenium-methionine
  • stilbenes and their derivatives eg stilbene oxide, trans-stil
  • Hydrotropes such as ethanol, isopropyl alcohol, or polyols can also be used to improve the flow behavior.
  • Polyols that come into consideration here preferably have 2 to 15 carbon atoms and at least two hydroxyl groups.
  • the polyols can also contain further functional groups, in particular amino groups, or be modified with nitrogen. Typical examples are
  • Alkylene glycols such as, for example, ethylene glycol, diethylene glycol, propylene glycol, butylene glycol, hexylene glycol and polyethylene glycols with an average molecular weight of 100 to 1,000 daltons;
  • Methyl compounds such as in particular trimethylolethane, trimethylolpropane, trimethylolbutane, pentaerythritol and dipentaerythritol; > Lower alkyl glucosides, especially those with 1 to 8 carbons in the alkyl radical, such as methyl and butyl glucoside;
  • Sugar alcohols with 5 to 12 carbon atoms such as sorbitol or mannitol, sugars with 5 to 12 carbon atoms, such as glucose or sucrose;
  • Dialcohol amines such as diethanolamine or 2-amino-1, 3-propanediol.
  • Natural fragrances are extracts of flowers (lily, lavender, roses, jasmine, neroli, ylang-ylang), stems and leaves (geranium, patchouli, petitgrain), fruits (anise, coriander, caraway, juniper), fruit peel (bergamot, lemon, Oranges), roots (mace, angelica, celery, cardamom, costus, iris, calmus), wood (pine, sandal, guaiac, cedar, rosewood), herbs and grasses (tarragon, lemongrass, sage, thyme), Needles and twigs (spruce, fir, pine, mountain pine), resins and balms (galbanum, elemi, benzoin, myrrh, olibanum, opoponax).
  • Typical synthetic fragrance compounds are products of the ester, ether, aldehyde, ketone, alcohol and hydrocarbon type. Fragrance compounds of the ester type are e.g.
  • the ethers include, for example, benzyl ethyl ether, the aldehydes e.g.
  • the linear alkanals with 8 to 18 carbon atoms citral, citronellal, citronellyloxyacetaldehyde, cyclamenaldehyde, hydroxycitronellal, lilial and bourgeonal, to the ketones e.g. the jonones, ⁇ -isomethylionone and methyl cedryl ketone, the alcohols anethole, citronellol, eugenol, isoeugenol, geraniol, linalool, phenylethyl alcohol and terpineol, the hydrocarbons mainly include the terpenes and balsams.
  • fragrance oils of lower volatility which are mostly used as aroma components, are also suitable as perfume oils, e.g. Sage oil, chamomile oil, clove oil, lemon balm oil, mint oil, cinnamon leaf oil, linden blossom oil, juniper berry oil, vetiver oil, oliban oil, galbanum oil, labolanum oil and lavandin oil.
  • bergamot oil dihydromyrcenol, lilial, lyral, citronellol, phenylethyl alcohol, ⁇ -hexylcinnamaldehyde, geraniol, benzyl acetone, cyclamen aldehyde, linalool, Boisambrene Forte, Ambroxan, indole, hedione, Sandelice, lemon oil, mandarin oil, orange oil, allyl amyl glycolate, Cyclovertal, lavandin oil, muscatel Sage oil, ß-Dar ⁇ ascone, geranium oil bourbon, cyclohexyl salicylate, Vertofix Coeur, Iso-E-Super, Fixolide NP, Evemyl, Iraldein gamma, phenylacetic acid, geranyl acetate, benzyl acetate, rose oxide, romiillate, i
  • the dyes which can be used are those which are suitable and approved for cosmetic purposes, as described, for example, in the publication "Cosmetic Dyes” of commission of the German Research Foundation, Verlag Chemie, Weinheim, 1984, pp. 81-106. These dyes are usually used in concentrations of 0.001 to 0.1% by weight, based on the mixture as a whole.
  • the total proportion of auxiliaries and additives can be 1 to 50, preferably 5 to 40,% by weight, based on the composition.
  • the agents can be produced by customary cold or hot processes; the phase inversion temperature method is preferably used.
  • compositions and properties of bar soaps (quantities as% by weight)

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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)
  • Health & Medical Sciences (AREA)
  • Molecular Biology (AREA)
  • Emergency Medicine (AREA)
  • Detergent Compositions (AREA)
  • Cosmetics (AREA)

Abstract

Nouveaux savons à base de détergents synthétiques, qui contiennent en tant que constituants tensioactifs des acides carboxyliques alcoxylés et en tant que substance odorante de l'amidon et/ou de la cellulose. Lesdits produits se caractérisent par une mousse particulièrement riche et onctueuse et par une sensation très agréable sur la peau.
PCT/EP2000/007331 1999-08-06 2000-07-28 Savons a base de detergents synthetiques Ceased WO2001010998A1 (fr)

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Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE102006010408A1 (de) * 2006-03-03 2007-09-06 Sebapharma Gmbh & Co. Syndetwaschstück

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2665256A (en) * 1948-01-23 1954-01-05 Atlas Powder Co Solid compositions containing polyoxyethylene ethers and urea
EP0459769A2 (fr) * 1990-06-01 1991-12-04 Unilever Plc Compositions de nettoyage avec une réduction de pâte, amélioration de la douceur ou les deux
DE19545136C1 (de) * 1995-12-04 1997-04-10 Henkel Kgaa Syndetstückseifen
US5756438A (en) * 1996-03-26 1998-05-26 The Andrew Jergens Company Personal cleansing product
WO1999010468A1 (fr) * 1997-08-25 1999-03-04 Cognis Deutschland Gmbh Savons a base de detergents synthetiques contenant des sulfates d'ester de polyglycol d'acide gras

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0777717A2 (fr) * 1994-08-25 1997-06-11 Ciba SC Holding AG Formulations tensioactives
DE19624416A1 (de) * 1996-06-19 1998-01-02 Henkel Kgaa Verfahren zur Herstellung von festen Wasch- oder Reinigungsmitteln

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2665256A (en) * 1948-01-23 1954-01-05 Atlas Powder Co Solid compositions containing polyoxyethylene ethers and urea
EP0459769A2 (fr) * 1990-06-01 1991-12-04 Unilever Plc Compositions de nettoyage avec une réduction de pâte, amélioration de la douceur ou les deux
DE19545136C1 (de) * 1995-12-04 1997-04-10 Henkel Kgaa Syndetstückseifen
US5756438A (en) * 1996-03-26 1998-05-26 The Andrew Jergens Company Personal cleansing product
WO1999010468A1 (fr) * 1997-08-25 1999-03-04 Cognis Deutschland Gmbh Savons a base de detergents synthetiques contenant des sulfates d'ester de polyglycol d'acide gras

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE102006010408A1 (de) * 2006-03-03 2007-09-06 Sebapharma Gmbh & Co. Syndetwaschstück

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