EP0970168A2 - Savons detersifs synthetiques - Google Patents

Savons detersifs synthetiques

Info

Publication number
EP0970168A2
EP0970168A2 EP97909333A EP97909333A EP0970168A2 EP 0970168 A2 EP0970168 A2 EP 0970168A2 EP 97909333 A EP97909333 A EP 97909333A EP 97909333 A EP97909333 A EP 97909333A EP 0970168 A2 EP0970168 A2 EP 0970168A2
Authority
EP
European Patent Office
Prior art keywords
fatty acid
alkyl
sulfates
ether
carbon atoms
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.)
Withdrawn
Application number
EP97909333A
Other languages
German (de)
English (en)
Inventor
Werner Seipel
Jörg KAHRE
Bernd Fabry
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
BASF Personal Care and Nutrition GmbH
Original Assignee
Cognis Deutschland GmbH and Co KG
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Cognis Deutschland GmbH and Co KG filed Critical Cognis Deutschland GmbH and Co KG
Publication of EP0970168A2 publication Critical patent/EP0970168A2/fr
Withdrawn legal-status Critical Current

Links

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
    • C11D3/0005—Other compounding ingredients characterised by their effect
    • C11D3/0094—High foaming 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
    • 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
    • C11D1/28—Sulfonation products derived from fatty acids or their derivatives, e.g. esters, amides
    • 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

Definitions

  • the invention relates to fatty acid-free syndet soaps containing monoglyceride (ether) sulfates and starch.
  • British Patent GB-B1 954 046 (Colgate) proposes bar soaps which contain 8 to 20% by weight of monoglyceride sulfates, 3 to 10% by weight of fatty acid isethionates and 45 to 65% by weight of fatty acid salts.
  • French so-called FR-B1 12 72 254 (Colgate) discloses bar soaps based on alkylbenzenesulfonates and fatty acid isethionates, which may contain monoglyceride sulfates as further anionic surfactants.
  • transparent bar soaps can contain 40 to 80% by weight of fatty acid salts, 4 to 11% by weight of anionic surfactants, for example monoglyceride sulfates, and glycerol.
  • European patent application EP-A1 0 318 729 (Colgate) describes a process for the production of bar soaps, in which a mixture of monoglyceride sulfate, soap and fatty acid is dissolved in isopropyl alcohol, dried in a falling film evaporator and then shaped into bars of soap.
  • European patent application EP-A1 0 411 220 proposes a "self-heating" soap which consists of two components, namely (a) a mixture of glycerol, surfactants (eg monoglyceride sulfates), fatty acid salts and a catalyst (sulfite + ascorbic acid
  • Non-foaming bar soaps are known from European patent application EP-A1 0 409 856 (McLaughlin), which contain 14 to 38% by weight of monoglyceride sulfates, 40 to 72% by weight of water-insoluble emulsifiers, and 0 to 25 % By weight of fillers and 2 to 12% by weight of water
  • the subject of European patent application EP-A2 0 592 073 is body cleansing agents, for example in the form of combibars or syndet soaps, which contain monoglyceride ether sulfates
  • German patent application DE-A1 43 31 297 Heenkel
  • soap bars 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 leave something to be desired. If free fatty acids are also used as refatting agents, severe corrosion problems can also occur in the manufacturing plants.
  • the object of the invention was therefore to provide bar soaps that are free from the disadvantages described. It was particularly important to take into account that new parts 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 and do not tend to crack during drying.
  • the invention relates to syndet soaps containing
  • bar soaps with improved foaming power and optimized skin feel can be produced in the absence of fatty acids or fatty acid salts if monoglyceride (ether) sulfates are used as the main surfactant component, preferably in anhydrous form, and starch is used as the builder.
  • the invention includes the knowledge that the mixtures are also outstandingly suitable for the industrial production of bar soaps, i.e. they are stable when stored in the air, are not hygrospcopic, deformable, but not too hard, and show no cracking when dried.
  • mixtures of monoglyceride (ether) sulfates with alkyl and / or alkenyl oligoglycosides and / or fatty acid N-alkyl glucamides are used as surfactant components.
  • Monoglyceride sulfates and monoglyceride ether sulfates are known anionic surfactants which can be obtained by the relevant methods of preparative organic chemistry.
  • the usual starting point for their preparation 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 0 561 825, EP-B1 0 561 999 (Henkel)].
  • the neutralized substances can be subjected to ultrafiltration in order to reduce the electrolyte content to a desired level [DE-A1 42 04 700 (Henkel)].
  • Overviews of the chemistry of the monoglyceride sulfates are, for example, by AKBiswas et al. in J.Am.Oil.Chem.Soc. 37, 171 (1960) and FUAhmed J.Am.Oil.Chem.Soc. 67, 8 (1990).
  • the monoglyceride (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 suitable for the purposes of the invention are the reaction products of lauric acid monoglyceride, coconut fatty acid monoglyceride, palmitic acid monoglyceride, stearic acid monoglycend, oleic acid monoglyceride and taig fatty acid monoglyceride as well as their ethylene oxide adducts or their form with sulfuric acid trioxide.
  • Monoglyceride sulfates of the formula (I) are preferably used in which R 1 CO represents a linear acyl radical having 8 to 18 carbon atoms.
  • the monoglyceride (ether) sulfates are preferably used as dry granules or powders, which can be obtained, for example, by drying aqueous pastes in a flash dryer.
  • Alkyl and alkenyl oligoglycosides 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.
  • 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 oligoglucosides.
  • 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, elaidyl alcohol, petroselinyl alcohol, arachyl alcohol, gadoleyl alcohol, behenyl alcohol, erucyl alcohol, brassidyl alcohol and their technical mixtures, as described above, which can be obtained as described above.
  • Fatty acid N-alkylpolyhydroxyalkylamides are nonionic surfactants which follow the formula (III)
  • R 3 CO for an aliphatic acyl radical having 6 to 22 carbon atoms
  • R 4 for hydrogen, 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):
  • the fatty acid N-alkylpolyhydroxyalkylamides used are preferably glucamides of the formula (IV) in which R 4 is methyl and R 3 CO is the acyl radical of caproic acid, caprylic acid, capric acid, lauric acid, myristic acid, palmitic acid, palmoleic acid, stearic acid, isostearic acid, oleic acid , Elaidic acid, petroselinic acid, linoleic acid, linolenic acid, arachic acid, gadoleic acid, behenic acid or erucic acid or their technical mixtures.
  • Fatty acid N-alkylglucamides of the formula (IV) which are obtained by reductive amination of glucose with methylamine and subsequent acylation with lauric acid or C 2 / ⁇ coconut fatty acid or a corresponding derivative are particularly preferred.
  • the polyhydroxyalkylamides can also be derived from maltose and palatinose.
  • wheat and / or maize starch is particularly preferred, which can be used untreated or preferably in an open, ie partially hydrolyzed form.
  • compounds of alkyl glucosides and starch are produced by subjecting aqueous slurries of the two components to drying with superheated steam, as is described, for example, in German patent application DE-A1 43 40 015 (Henkel). Reference is hereby expressly made to the teaching of this document. However, it is also possible to carry out the drying, if appropriate together with the glycosides, by another process, for example in a horizontally arranged thin-film evaporator (“flash dryer”). Dilute aqueous preparations with alkyl glucosides and starch are known for example from the publications EP-A1 0 502 616 (Unilever) and DE-A1 40 11 487 (Henkel).
  • the syndet soaps according to the invention can also contain anionic, nonionic, cationic and / or amphoteric or zwitterionic surfactants as minor constituents.
  • anionic surfactants are alkylbenzenesulfonates, alkanesulfonates, olefin sulfonates, alkyl ether sulfonates, glycerol ether sulfonates, ⁇ -methyl ester sulfonates, sulfofatty acids, alkyl sulfates, fatty alcohol ether sulfates, glycerol ether sulfates, hydroxymixed ether sulfates, and sulfate amateo- (fatty acid amide), fatty acid amide (fatty acid amide), fatty acid amide (fatty acid amide), fatty acid amide (fatty acid amide), fatty acid amide (fatty acid amide), fatty acid amide (fatty acid amide), fatty acid
  • anionic surfactants contain polyglycol ether chains, they can have a conventional, but preferably a narrow, homolog distribution.
  • Typical examples of nonionic surfactants are fatty alcohol polyglycol ethers, alkylphenol polyglycol ethers, fatty acid polyglycol esters, fatty acid amide polyglycol ethers, fatty amine polyglycol ethers, alkoxylated triglycerides, mixed ethers or mixed formals, protein hydrolyzates (especially vegetable products based on wheat) and polyol fatty acid sorbate esters, sugar ester, polysorbate sorbate esters, sugar ester.
  • nonionic surfactants contain polyglycol ether chains, they can have a conventional, but preferably a narrow, homolog distribution.
  • Typical examples of cationic surfactants are quaternary ammonium compounds and ester quats, in particular quaternized fatty acid trialkanolamine ester salts.
  • Typical examples of amphoteric or zwitterionic surfactants are alkyl betaines, alkyl amido betaines, amino propionates, aminoglycinates, imidazolinium betaines and sulfobetaines.
  • the surfactants mentioned are exclusively known compounds. With regard to the structure and manufacture of these substances, reference is made to relevant reviews, for example J.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, pp. 123-217.
  • Preferred feedstocks are alkyl sulfates, alkyl ether sulfates, sulfosuccinates, ether carboxylic acids, fatty acid isethionates, protein fatty acid condensates and / or betaines. Syndet soaps
  • Syndet soaps with a particularly beneficial skin feel and creamy foam contain the ingredients in the following amounts:
  • syndet soaps have the following composition:
  • fatty acid N-alkylpolyhydroxyalkylamides preferably fatty acid N-alkylglucamides.
  • fatty alcohols and polyethylene glycol ethers are fatty alcohols and polyethylene glycol ethers.
  • suitable fatty alcohols are lauryl alcohol, myristyl 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.
  • the syndet soaps according to the invention are practically free of free fatty acids or fatty acid salts, ie the content of these substances is below 0.5% by weight. Nevertheless, the soaps ran a surprisingly high amount of a particularly creamy foam and also convey a very pleasant feeling on the skin. Auxiliaries and additives
  • the syndet soaps can contain oil additives, emulsifiers, superfatting agents, stabilizers, waxes, consistency enhancers, cation polymers, silicone compounds, biogenic agents, preservatives, hydrotropes, solubilizers, dyes and fragrances as further auxiliaries and additives.
  • Suitable oil bodies are, for example, Guerbet alcohols preferably containing 8 to 10 carbon atoms, esters of linear C6-C come based on fatty alcohols having 6 to 18, 20 fatty acids with linear C ⁇ -C ⁇ o-fatty alcohols, esters of branched C6-C ⁇ 3-carboxylic acids with linear C6-C20 fatty alcohols, esters of linear C ⁇ -cis-fatty acids with branched alcohols, especially 2-ethylhexanol, esters of linear and / or branched fatty acids with polyhydric alcohols (such as dimer diol or trimer triol) and / or Guerbet alcohols, triglycerides based on C6-C ⁇ 0 fatty acids, vegetable oils, branched primary alcohols, substituted cyclohexanes, Guerbet carbonates, dialkyl ethers and / or aliphatic or naphthenic hydrocarbons.
  • esters of linear C6-C come based
  • Suitable emulsifiers are nonionic surfactants from at least one of the following groups:
  • polyglycerol esters such as e.g. Polyglycerol polyricinoleate or polyglycerol poly-12-hydroxystearate. Mixtures of compounds from several of these classes of substances are also suitable;
  • Partial esters based on linear, branched, unsaturated or saturated C ⁇ 2/2 2 fatty acids
  • Ricinoleic acid and 12-hydroxystearic acid and glycerin polyglycerin, pentaerythritol, dipentaerythritol, sugar alcohols (e.g. sorbitol) and polyglucosides (e.g. cellulose);
  • the adducts of ethylene oxide and / or of propylene oxide with fatty alcohols, fatty acids, alkylphenols, glycerol mono- and diesters as well as sorbitan mono- and diesters of fatty acids or with castor oil are known, commercially available products. These are homolog mixtures, the middle of which Degree of alkoxylation corresponds to the ratio of the amounts of ethylene oxide and / or propylene oxide and substrate with which the addition reaction is carried out.
  • C 2 / i8 fatty acid monoesters and diesters of adducts of ethylene oxide with glycerol are known from DE-PS 20 24 051 as refatting agents for cosmetic preparations.
  • Zwitterionic surfactants can also be used as emulsifiers.
  • Zwitterionic surfactants are surface-active compounds that contain at least one quaternary ammonium group and at least one carboxylate and one sulfonate group in the molecule.
  • Particularly suitable zwitterionic surfactants are the so-called betaines, such as the N-alkyl-N, N-dimethylammonium glycinate, for example coconut alkyldimethylammonium glycinate, N-acylamino propyl-N, N-dimethylammonium glycinate, for example coconut acylaminopropyldimethylammonium glycinate, and 2-alkyl-3-carboxyl -3-hydroxyethylimidazolines each having 8 to 18 carbon atoms in the alkyl or acyl group and the cocoacylaminoethylhydroxyethylcarboxymethylglycinate.
  • betaines such as the N-alkyl-N, N-dimethylammonium glycinate, for example coconut alkyldimethylammonium glycinate, N-acylamino propyl-N, N-dimethylammonium glycinate, for
  • fatty acid amide derivative known under the CTFA name Cocamidopropyl Betaine is particularly preferred.
  • Suitable emulsifiers are ampholytic surfactants.
  • Ampholytic surfactants are surface-active compounds which, in addition to a C ⁇ -alkyl or -acyl group, contain at least one free amino group and at least one -COOH or -SO3H group in the molecule and are capable of forming internal salts.
  • ampholytic surfactants are N-alkylglycines, N-alkylpropionic acids, N-alkylaminobutyric acids, N-alkyliminodipropionic acids, N-hydroxyethyl-N-alkylamidopropylglycines, N-alkyltaurines, N-alkylsarcosines, 2-alkylaminopropionic acids and alkylaminoacetic acids, each with about 8 to 18 carbon atoms in the alkyl group.
  • Particularly preferred ampholytic surfactants are N-coconut alkyl aminopropionate, coconut acylaminoethyl aminopropionate and C 2 / i8 acyl sarcosine.
  • quaternary emulsifiers are also suitable, those of the ester quat type, preferably methyl-quaternized difatty acid triethanolamine ester salts, being particularly preferred.
  • Substances such as, for example, lanolin and lecithin and polyethoxylated or acylated lanolin and lecithin derivatives, polyol fatty acid esters, monoglycerides and fatty acid alkanolamides can be used as superfatting agents, the latter simultaneously serving as foam stabilizers.
  • As consistency agents primarily fatty alcohols with 12 to 22 and preferably 16 to 18 carbon atoms come into consideration. A combination of these substances with alkyl oligoglucosides and / or fatty acid N-methyl glucamides of the same chain length and / or polyglycerol poly-12-hydroxystearates is preferred.
  • Suitable cationic polymers are, for example, cationic cellulose derivatives, cationic starch, copolymers of diallylammonium salts and acrylamides, quaternized vinylpyrrolidone / vinylimidazole polymers such as e.g. Luviquat® (BASF AG, Ludwigshafen / FRG), condensation products of polyglycols and amines, quaternized collagen polypeptides such as lauryldimonium hydroxypropyl hydrolyzed collagen (Lamequat ⁇ L, Grünau GmbH), quaternized wheat polypeptides,
  • cationic silicone polymers such as e.g. Amidomethicone or Dow Corning, Dow Corning Co./US, copolymers of adipic acid and dimethylaminohydroxypropyldiethylenetrimamine (Cartaretine®, Sandoz / CH), polyaminopolyamides such as e.g. described in FR-A 22 52 840 and its crosslinked water-soluble polymers, cationic chitin derivatives such as quaternized chitosan, optionally microcrystalline, condensation products of dihaloalkylene such as e.g.
  • Dibromobutane with bisdialkylamines such as Bis-dimethylamino-1, 3-propane, cationic guar gum such as e.g. Jaguar® CBS, Jaguar® C-17, Jaguar® C-16 from Celanese / US, quaternized ammonium salt polymers such as e.g. Mirapol® A-15, Mirapol® AD-1, Mirapol® AZ-1 from Miranol / US.
  • Suitable silicone compounds are, for example, dimethylpolysiloxanes, methylphenylpolysiloxanes, cyclic silicones and amino-, fatty acid-, alcohol-, polyether-, epoxy-, fluorine- and / or alkyl-modified silicone compounds, which can be both liquid and resinous at room temperature.
  • Typical examples of fats are glycerides; beeswax, paraffin wax or microwaxes may be used as waxes, if appropriate in combination with hydrophilic waxes, for example cetylstearyl alcohol.
  • Metal salts of fatty acids such as magnesium, aluminum and / or zinc stearate can be used as stabilizers.
  • Biogenic active substances are understood to mean, for example, bisabolol, allantoin, phytantriol, panthenol, AHA acids, plant extracts and vitamin complexes.
  • Suitable preservatives are, for example, phenoxyethanol, formaldehyde solution, parabens, pentanediol or sorbic acid.
  • the dyes which can be used are those substances which are suitable and approved for cosmetic purposes, as compiled, for example, in the publication "Cosmetic Dyes” by the Dye Commission of the German Research Foundation, Verlag Chemie, Weinheim, 1984, pp. 81-106. These dyes are commonly used in Concentrations of 0.001 to 0.1 wt .-%, 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.
  • compositions water ad 100 wt .-%) and properties of bar soaps
  • Titanium dioxide 1.0 1.0
  • Example and comparative example show clear advantages for the syndetbar formulation according to the invention according to all test criteria: the syndetbar has a very pleasant feeling on the skin (+++) and develops a large amount of creamy friction foam (+++). It shows no tendency to absorb water (-) or crack after drying (-), but it is very malleable (+++). In contrast, the skin feel and foaming power of the Combibar formulation are only average (+), the pieces are comparatively difficult to deform (+) and show both a tendency to crack (+) and water absorption (+).

Abstract

L'invention concerne de nouveaux savons détersifs synthétiques contenant des monoglycéride(éther)sulfates comme composants tensioactifs et de l'amidon comme adjuvant. Ces produits se distinguent par leur mousse particulièrement abondante et crémeuse et leur sensation optimale sur la peau.
EP97909333A 1996-10-07 1997-09-29 Savons detersifs synthetiques Withdrawn EP0970168A2 (fr)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
DE19641277 1996-10-07
DE1996141277 DE19641277C2 (de) 1996-10-07 1996-10-07 Syndetseifen
PCT/EP1997/005346 WO1998015606A2 (fr) 1996-10-07 1997-09-29 Savons detersifs synthetiques

Publications (1)

Publication Number Publication Date
EP0970168A2 true EP0970168A2 (fr) 2000-01-12

Family

ID=7808058

Family Applications (1)

Application Number Title Priority Date Filing Date
EP97909333A Withdrawn EP0970168A2 (fr) 1996-10-07 1997-09-29 Savons detersifs synthetiques

Country Status (4)

Country Link
EP (1) EP0970168A2 (fr)
JP (1) JP2002512642A (fr)
DE (1) DE19641277C2 (fr)
WO (1) WO1998015606A2 (fr)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE10015000A1 (de) * 2000-03-25 2001-09-27 Cognis Deutschland Gmbh Syndetseifen
DE10035210A1 (de) * 2000-07-20 2002-01-31 Beiersdorf Ag Geformtes Seifenprodukt, enthaltend Talkum, eine oder mehrere Fettsäuren in Form ihrer Alkaliseifen und ein oder mehrere kationische Tenside bei gleichzeitiger Abwesenheit von Alkyl-(oligo)-glycosiden
US11479743B2 (en) 2020-02-17 2022-10-25 Ji Min SON Natural soap composition having elasticity viscoelasticity and ductility without containing polyvinyl alcohol and borax and method of preparing the same

Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
NL254807A (fr) * 1959-08-12
DE3011813C2 (de) * 1980-03-27 1984-12-06 Zschimmer & Schwarz Gmbh & Co Chemische Fabriken, 5420 Lahnstein Stückförmiges Reinigungsmittel
US4808322A (en) * 1988-03-10 1989-02-28 Mclaughlin James H Skin cleansing-cream conditioning bar
GB2277325A (en) * 1993-04-23 1994-10-26 Unilever Plc Detergent bar
DE4331297A1 (de) * 1993-09-15 1995-03-16 Henkel Kgaa Stückseifen

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
See references of WO9815606A3 *

Also Published As

Publication number Publication date
WO1998015606A3 (fr) 1998-06-18
DE19641277C2 (de) 1998-11-05
WO1998015606A2 (fr) 1998-04-16
DE19641277A1 (de) 1998-04-30
JP2002512642A (ja) 2002-04-23

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