EP1863825A1

EP1863825A1 - Novel surfactants and novel emulsifiers made from disaccharides

Info

Publication number: EP1863825A1
Application number: EP06723701A
Authority: EP
Inventors: Joerg Schreiber; Goetz Milkereit; Sven Gerber; Volkmar Vill
Original assignee: Beiersdorf AG
Current assignee: Beiersdorf AG
Priority date: 2005-03-24
Filing date: 2006-03-24
Publication date: 2007-12-12
Also published as: DE102005014424A1; EP1980567A1; CH698948B1; WO2006100091A1

Abstract

The invention relates to compounds of formula A-(B)x-C where A = a reducing di- or tri-saccharide, B = 2 - 4C polyvalent alcohol or the derivatives thereof, C = a branched or unbranched, saturated or unsaturated, fatty alcohol with 8 to 22, preferably 8 to 14 or 14 to 22, more preferably to 20 carbon atoms, A has a glycosidic link in the 1 position to B, B is etherified with C and x = 1 to 50.

Description

description

New surfactants and new emulsifiers based on disaccharides

The present invention relates to novel surfactants and emulsifiers based on disaccharides. These are characterized in particular by a special foaming behavior and a special mildness when applied to the skin. In addition, a subgroup is suitable as a gelling agent.

The prior art knows ionic surfactants such as lauryl ether sulfate, lauryl sulfate. These are the standard surfactants used in personal care products. They are characterized by high use concentration (of 8-20 wt.%) And are only slightly friendly to the skin, so their properties are optimized by blending, for example with cosurfactants such as cocamidopropyl betaine and cocoamphoacetate. To obtain a hand-foaming preparation usually 10-15 wt.% Of lauryl ether sulfate are used. Furthermore, lauryl ether sulfate or lauryl sulfate is an anionic surfactant. The combination with cationic surfactants is often a major problem due to precipitate formation in aqueous systems (opposite charge of anion and cationic surfactant). Furthermore, cationic polymers for corresponding anionic surfactants are often problematic for the same reason.

To improve the skin compatibility of lauryl ether sulfate formulations, nonionic surfactants such as alkylpolyglycosides (APG) are also used. APG is the standard surfactant for detergents and cosmetic preparations. However, the composition of this surfactant mixture is extremely inhomogeneous. Its properties can not therefore be attributed to a single compound. A known APG (Plantaren 2000 UP, Cognis) contains, for example, 1% by weight of C ₆ -glucosides, 33-40% by weight of Cβ-glucosides, 21-28% by weight of C ₁₀ -glucosides, 27-32% by weight. C ₁₂ glucosides, 9-12 C ₁₄ glucosides, 1 C ₁₅ glucosides and higher polymers and free fatty alcohol. It should also be noted that this is still a mixture of α- and ß-anomers of glucosides. The preparation of the hydrophilic component of the APG takes place a) by hydrolysis of starch or dextrose syrup or b) of anhydrous glucose (or glucose monohydrate). This hydrophilic component is converted in the starch hydrolysis route with butanol in the corresponding glycoside and then umacetalisiert with the long-chain fatty alcohol. The synthetic route via the anhydrous glucose uses the direct acetalization with the long-chain fatty alcohol in the corresponding glycoside. Disaccharide-based surfactants have hitherto been of lesser importance in cosmetics, as detergents or in the food industry. Alkyl glycosides with disaccharide carbohydrate head groups have also been described in the literature, for example maltosides, lactosides or melibiosides having alkyl chain lengths of 10-20 carbon atoms. A disadvantage of these compounds is their poor water solubility due to a high Krafft temperature. They are therefore not suitable as surfactants.

Another disadvantage of alkyl glycosides, such as APGs, is their low foaming property in water, which further requires the use of lauryl ether sulfate, lauryl sulfate or other cosurfactants. Furthermore, these compounds are unable to form gels in aqueous solution when the use concentration in water is less than 15% by weight.

Unexpected and unforeseeable for the skilled person are the disadvantages of

Prior art compounds according to the formula A- (B) _x -C wherein A is a reducing di- or trisaccharide,

B is a polyhydric alcohol having 2 to 4 C atoms or its derivative,

C is a branched or unbranched, saturated or unsaturated fatty alcohol radical having 8 to 22, particularly preferably 10 to 14 or 14 to 22, very particularly preferably up to 20

C atoms is glycosidically linked to B in position 1,

B is etherified with C and x has the value 1 to 50, eliminated.

Such compounds have the following advantages: they are very good foaming agents at room temperature and also at higher temperature, for example at 50 ^° C., they form very stable foams, they form a large amount of foam at low use concentrations, They allow a very good foaming also for mixtures due to the manufacturing process, they are easy to produce, certain compounds allow gelation, they are miscible with cosurfactants, they are good to very well tolerated.

A known method to improve the solubility of amphiphiles is the ethoxylation of hydroxy groups. Thus, e.g. US3640998 the preparation of ethoxylated alkyl polyglucosides in which all free hydroxy groups are ethoxylated. Targeted ethoxylation in the form of ethoxylated alkyl disaccharides has rarely been disclosed. The use of ethylene glycol as a spacer between the alkyl chain of a fatty alcohol and the carbohydrate head group at the anomeric center has hitherto been known only for a few compounds and the properties were investigated only with regard to a possible medical application (Bendas, G., Wilhelm, F., Richter , W., Nuhn, P., Eur. J. Pharm. Sci., 4, 1996, 211ff .; Nuhn, P., Pfaff, T., Bendas, G., Wilhelm, F., Chatterjee, SK, Arch Pharm., 327, 1994, 429ff.). The spacers serve in this case to increase the distance of the carbohydrate head group to the surface of the liposome. Furthermore, phospholipids are used here with the substituted sugars for liposome formation. The advantages of a targeted ethoxylation in the form of ethoxylated alkyl disaccharides based on lactose, maltose, mellibiose without phospholipids is not known. About foaming, gelation or their suitability as a surfactant is not known.

In the present invention, various derivatives having the structure disaccharide spacer alkyl chain have now been investigated:

A - B - C with A = carbohydrate head group

B = spacer C = hydrophobic chain

It was found that by using a spacer, the solubility of the compounds in water could be decidedly improved. Also, solely the use of the anomeric mixtures, which are caused by the manufacturing process or by Mixing of the anomers, leads to an improved solubility. Moreover, it has been found that the use of a glycol spacer allows the gelation of lauryl lactosides. The foam behavior of the compounds is also improved

105 versus a compound without the spacer. Furthermore, a fine foam can be achieved by blending with cosurfactants. The compounds are better tolerated in terms of their skin tolerance than the standard surfactants lauryl sulfate and lauryl ether sulfate. Furthermore, to obtain a foam, a lower use concentration (depending on the selected disaccharide alkyl glycoside about 1-5

110% by weight).

As a particularly advantageous embodiments of the invention, the

Objects of the other claims exposed.

As unit A are glycosidically linked disaccharides and z.T. glycoside

115 linked trisaccharides.

Also suitable are pure anomers and mixtures of the anomers, by physical mixing or due to the manufacturing process, and mixtures of the compounds with each other, so lactosides, melibiosides, maltosides, cellobiose which are used as each pure alpha or beta anomer or even that

120 anomer mixture,

Mixtures of lactosides with melibiosides, mixtures of lactosides with maltosides and / or mixtures of meliosides and maltosides, in each case pure or as anomer mixtures.

125 lactose can be purchased from Sigma, Fucka, Biolac (Aria Food Corporation, 31097 Harbansen). Furthermore, the monolydrate of lactose (Variolac 99 edible, Biolac) can also be used in addition to anhydrous lactose.

Particularly suitable for use as surfactants or emulsifiers disaccharide 130 units are lactose, melibiose and maltose and cellobiose:

Maltose (time)

According to the invention, both their monohydrates and the anhydrous compounds can be used, particularly preferably the monohydrates.

Suitable units B (spacer) include ethylene glycol (EG) _1, diethylene glycol, triethylene glycol, tetraethylene glycol, propylene glycol (PG), dipropylene glycol, glycerol, butylene glycol, pentaerythritol. Particularly suitable units B are the following structures:

140

Very particular preference is given to ethylene glycol, diethylene glycol, triethylene glycol, tetraethylene glycol, propane-1,2-diol, propane-1,3-diol, dipropylene glycol, glycerol, butanediol, pentaerythritol.

Particularly suitable units C for use as a surfactant are generally alkyl chains having 8-14 C atoms, which may be linear, saturated, branched or unsaturated. Especially preferred for surfactants are linear and saturated alkyl chains having 8-12 carbon atoms. Particularly preferred gel formers are as unit C linear, saturated alkyl chains having 150 12 C-atoms and particularly preferably those having a unit B which has on average one in the form of a single EO unit. Products of lactose and the fatty alcohol narrow range ethoxylates such as Berol 260 or Berol 266 (Akzo) can be used with particular preference as gel-forming products according to the invention. Preferred for use as emulsifiers are compounds having chain lengths of 12-155 22 C atoms. Particularly preferred are then C16 to C18 alkyl chains.

It is advantageous if the ratio between spacer (B) and chain (C) is kept constant, in the sense that the chain length grows with the spacer length.

Particularly preferred compounds are in particular as foaming compounds:

160

3.) 170

MaI-EHG

175 MaI-EHG

Lac-EnC12 with n = 2-4

180

Lac-α-EnC12 with n = 2-4

Lac-EnC14 with n = 1-4

190 Lac-α-EnC14 with n = 1-4

n = 1

MaI-EC-CI 2

MeI-EG-CI 2

205

Also favorable are lactosides of technical fatty alcohol ethoxylates, in particular the following compounds 13 to 16:

210

Lac-EG _π C10

Fatty alcohol ethoxylate: Lutensol ^® ON 30 n = mainly 3 according to manufacturer

215

Lac-EG _n C9-C11

220 fatty alcohol ethoxylate: Berol 260 n = mainly 4 according to the manufacturer m = C8-C10 according to the manufacturer

225

230

Fatty alcohol ethoxylate: Berol 533

235 n = mainly 2 according to the manufacturer

240

Fatty alcohol ethoxylate: Berol 533 n = mainly 3 according to manufacturer

245

to 1.) (2'-Dodecyloxyethyl) 4-O- (β-D-galactopyranosyl) -β-D-glucopyranoside

(Lac-EC-C12)

250 to 2.) (2'-Dodecyloxypropyl) 4-O- (β-D-galactopyranosyl) -β-D-glucopyranoside (Lac-PG-C12),

to 3.) (2'-Dodecyloxyethyl) 4-O- (β-D-galactopyranosyl) -α-D-glucopyranoside

(Lac-α-EG-C12), 255 to 4.) (2'-Dodecyloxypropyl) 4-O- (β-D-galactopyranosyl) -α-D-glucopyranoside

(Lac-α-PG-C12). to 5.) 1-0- (2'-ethylhexyoxy) -3-0- (4 "-0-α-D-glucopyranosyl) -D-glucopyranosyl) -glycerol

(MaI-EHG) to 6.) 1-0- (2'-ethylhexyoxy) -2-0- (4 "-0-α-D-glucopyranosyl) -D-glucopyranosyl) -glycerol 260 (MaI-EHG) 7.) (2 '- (2 "-Dodecyloxyethyloxy) ethyl) 4-O- (β-D-galactopyranosyl) -β-D-glucopyranoside (Lac-EG2C12)

(2 '- (2 "- (2' '' - Dodecyloxyethyloxy) ethyloxy) ethyl) 4-O- (β-D-galactopyranosyl) -β-D-glucopyranoside (Lac-EG3C12) 265 (2 '- (2 "- (2" '- (2 "" - dodecyloxyethyloxy) ethyloxy) ethyloxy) ethyl) 4-O- (β-D-galactopyranosyl) -β-D-glucopyranoside (Lac-EG4C12) to 8.) ( 2 '- (2 "-dodecyloxyethyloxy) ethyl) 4-O- (β-D-galactopyranosyl) -α-D-glucopyranoside (Lac-α-EG2C12)

270 (2 '- (2 "- (2''' - Dodecyloxyethyloxy) ethyloxy) ethyl) 4-O- (β-D-galactopyranosyl) -α-D-glucopyranoside (Lac-α-EG3C12) (2 '- (2 "- (2'" - (2 "" - Dodecyloxyethyloxy) -ethyloxy) -ethyloxy) -ethyl) 4-O- (β-D-galactopyranosyl) -α-D-glucopyranoside (Lac-α -EG4C12) to 9.) (2'-tetradecyloxyethyl) 4-O- (β-D-galactopyranosyl) -β-D-glucopyranoside 275 (Lac-EG1C14)

(2 '- (2 "-tetradecyloxyethyloxy) ethyl) 4-O- (β-D-galactopyranosyl) -β-D-glucopyranoside

(Lac-EG2C14)

(2 '- (2 "- (2" -tetradecyloxyethyloxy) -ethyloxy) -ethyl) 4-O- (β-D-galactopyranosyl) -β-280 D-glucopyranoside (Lac-EG3C14)

(2 '- (2 "- (2' '' - (2 '' '- Tetradecyloxyethyloxy) ethyloxy) ethyloxy) ethyl) 4-O- (β-D-galactopyranosyl) -β-D-glucopyranoside (Lac-EG4C14 ) to 10.) (2'-Tetradecyloxyethyl) 4-O- (β-D-galactopyranosyl) -α-D-glucopyranoside

(Lac-α-EG1C14) 285 (2 '- (2 "-tetradecyloxyethyloxy) -ethyl) 4-O- (β-D-galactopyranosyl) -α-D-glucopyranoside

(Α-Lac-EG2C14)

(2 '- (2 "- (2" -tetradecyloxyethyloxy) -ethyloxy) -ethyl) 4-O- (β-D-galactopyranosyl) -α-

D-glucopyranoside 290 (Lac-α-EG3C14)

(2 '- (2 "- (2' '' - (2 '' '- tetradecyloxyethyloxy) ethyloxy) ethyloxy) ethyl) 4-O- (β-D-galactopyranosyl) -α-D-glucopyranoside

(Α-Lac-EG4C14)

295 to 10a)

(2 '- (Octyloxyethyl) -4-0- (β-D-galactopyranosyl) -β-D-glucopyranoside (Lac-EGC8)

to 11.) (2'-Dodecyloxyethyl) 4-O- (α-D-glucopyranosyl) -β-D-glucopyranoside 300 (MaI-EG-CI 2) to 12.) (2'-Dodecyloxyethyl) 6-O- (α-D-galactopyranosyl) -β-D-glucopyranoside (MeI-EG-CI 2)

305 To 13.)

Lactoside: Lac-EG ₃ C10 and Lac-α-EG ₃ C10

310

(2- [2- [2- (Decyloxy) ethoxy] ethoxy] ethyl) -4-0- (β-D-galactopyranosyl) -β-D-glucopyranoside (Lac-EGjClO)

315 (2- [2- [2- (decyloxy) ethoxy] ethoxy] ethyl) -4-0- (β-D-galactopyranosyl) -α-D-glucopyranoside

(Α-Lac-EGjCIO)

320 to 14.)

Lactoside: Lac-EG ₄ C9 and Lac-α-EG ₄ C9 Lactoside: Lac-EG ₄ C10 and Lac-α-EG ₄ C10 Lactoside: Lac-EG ₄ C11 and Lac-α-EG ₄ C11

325

(2- [2- [2- [2- (Nonyloxy) ethoxy] ethoxy] ethoxy)] ethyl) -4-O- (β-D-galactopyranosyl) -β-D-glucopyranoside (Lac-EG ₄ C9)

330 (2- [2- [2- [2- (Nonyloxy) ethoxy] ethoxy] ethoxy)] ethyl) -4-O- (β-D-galactopyranosyl) -α-D-glucopyranoside (Lac-α-EG ₄ C9)

335 (2- [2- [2- [2- (decyloxy) ethoxy] ethoxy] ethoxy)] ethyl) -4-0- (β-D-galactopyranosyl) -β-D-glucopyranoside Lac-EG ₄ C10

(2- [2- [2- [2- (Decyloxy) ethoxy] ethoxy] ethoxy)] ethyl) -4-0- (β-D-galactopyranosyl) -α-D-340 glucopyranoside (Lac-α-EG ₄ C10)

(2- [2- [2- [2- (Undecyloxy) ethoxy] ethoxy] ethoxy)] ethyl) -4-0- (β-D-galactopyranosyl) -β-D-glucopyranoside 345 Lac-EG ₄ C11 (2- [2- [2- [2- (undecyloxy) ethoxy] ethoxy] ethoxy)] ethyl) -4-O- (β-D-galactopyranosyl) -α-D-glucopyranoside

(Lac-α-EG ₄ C11)

350

To 15.)

Lactoside: Lac-EG ₂ -C11 and Lac-α-EG ₂ -C11

355

(2- [2- (Ucydecyloxy) ethoxy] ethyl) -4-O- (β-D-galactopyranosyl) -β-D-glucopyranoside (Lac-EG ₂ C11)

(2- [2- (Undecyloxy) ethoxy] ethyl) -4-O- (β-D-galactopyranosyl) -α-D-glucopyranoside 360 (Lac-α-EGzCH)

To 16.)

365 Lactoside: LaC-EG ₃ -CH and Lac-α-EG ₃ -C11

(2- [2- [2- (undecyloxy) ethoxy] ethoxy] ethyl) -4-0- (β-D-galactopyranosyl) -β-D-glucopyranoside (Lac-EGjCH) 370

(2- [2- [2- (undecyloxy) ethoxy] ethoxy] ethyl) -4-O- (β-D-galactopyranosyl) -α-D-glucopyranoside

(Lac-α-EG ₃ C11)

375

380 Lactosides that form gels:

Particularly suitable gelling agents are β-, 4-linked saccharides, e.g.

Lactose and cellobiose. The surfactant forms a gel here and foams in addition. 385

Particularly suitable gelling agents are the β-anomers of Lac-EG-C12 or

Lac-PG-C12 proved.

Also suitable are lactosides, the technical narrow-range ethoxylates such as Berol® 260

(C9-C11 EG _n ; n = 4 according to Akzo). 390

foaming agents:

As sole compounds, the compounds Lac-EG-C12, 395 Mal-EG-C12 and Mel-EG-C12 are distinguished as good foaming agents.

Furthermore, the mixture of Lac-PG-C12 with MaI-EHG shows a very good foaming behavior.

Furthermore, the mixtures are those from the reaction of lactose or lactose monohydrate with short-chain, ethoxylated fatty alcohols such as laureth-2 and laureth-3 (Lac-Laureth-2 or Lac-Laureth-3 or Lac-EG2C12 and Lac-EG3C12 ), particularly good foaming agents.

Short-chain fatty alcohol ethoxylates, such as laureth-2 and laureth-3, are available from Sasol (Marlipal) and from Akzo Nobel (Berol 260, 266, 533, 532, 840), (Ethylan 405 1005) and from BASF (Lutensol ON 30). Lutensol ON 30 represents decyl alcohol with 3 EO units in a technical mixture. Therefore, there are also molecules with higher and lower numbers of EO units. The fatty alcohol can also be partially or completely present as an iso-fatty alcohol. The same applies to all technical EO-fatty alcohols adducts. Berol 260, 266, 840 and Ethylan 1005 belong to the "narrow-range" fatty alcohol ethoxylates, which are characterized by a particularly narrow distribution of ethoxylation, for example Berol 260 is linked on average to four ethyleneoxy units and the distribution curve is narrower to standard ethoxylates, however, in the Berol 260 compounds with 1 to 16 Be contained ethyleneoxy units. More details can be found in the product data sheet "Berol 260, 415 266, 840, Ethylan 1005" of the manufacturer Akzo Nobel from September 2005.

Among the fatty alcohol ethoxylates available from companies such as Sasol:

The skilled person knows that this is not pure Laureth-2 or Laureth-3, but rather is the ethoxylated lauryl alcohol with 1-5 or more EO units.

Accordingly, disaccharide (e.g., lactose) appropriately reacted with commercially available laureth-x (x = degree of ethoxylation) is not exactly reproduced by the structures described above.

Furthermore, commercially available laureth-x (x = degree of ethoxylation) is not purely related to the fatty alcohol and therefore can be both longer and shorter chain

425 contain fatty alcohols as lauryl alcohol.

Accordingly, the designation for the lactoside "Lac-Laureth-2" or "Lac-Laureth-3" as the reaction product of technical laureth-2 or laureth-3 with lactose should be understood to mean that shorter or longer-chain fatty alcohols ethoxylated here can.

430

Furthermore, pure fatty alcohol ethoxylates can also be used for the reaction with the particular disaccharide.

Furthermore, it could be shown that the foaming power of the invention

435 lactosides, maltosides, melibiosides at high temperatures (eg 50 ⁰ C) on the same

Level as at 25 ° C or even higher (ex 10-11). So are Lac-EG-C12,

MaI-EG-CI 2 and MeI-EG-CI 2 at 50 ⁰ C significantly better foaming agent than

Sodium lauryl ether sulphate (SLES). This property is both instantaneous

Determination (immediate volume) and after 30 minutes (30 min.

440 volume).

This is of particular interest for commercial hot-temperature applications of the surfactants according to the invention, for example for washing powders, liquid detergents, textile washing powders or pellets, dishwasher detergents or also for hot drinks (which are intended to foam, eg Capucchino) or as foods which are prepared or treated in the heat , Furthermore, the surfactants of the invention are interesting as preparations for a hot bubble bath. Furthermore, the inventively substituted disaccharides can also be reacted with glycerol as a spacer and a hydrophobic group.

For example, the corresponding maltoside can be prepared from maltose and ethylhexylglycerol (see later section Foam behavior on hair). The maltosides can be advantageously mixed with lactosides, for example WIaI-EHG with Lac-PG-C12. Further compounds of the invention are (2'-hexadecyloxy-ethyl) 4-O- (β-D-

455 galactopyranosyl) -β-D-glucopyranoside, (2'-dodecyloxyethyl) -4-O- (α-D-glucopyranosyl) -β-D-glucopyranoside, (2'-tetradecyloxy-ethyl) 4-O- (α -D-glucopyranosyl) -β-D-glucopyranoside, (2'-hexadecyloxy-ethyl) -4-O- (α-D-glucopyranosyl) -β-D-glucopyranoside, (2'-dodecyloxyethyl) 6-O- (α-D-galactopyranosyl) -β-D-glucopyranoside, (2-tetradecyloxy-ethyl) 6-O- (α-D-galactopyranosyl) -β-D-glucopyranoside, (2'-hexadecyloxy)

460 ethyl) 6-O- (α-D-galactopyranosyl) -β-D-glucopyranoside, (2'-dodecyloxypropyl) -4-O- (α-D-glucopyranosyl) -β-D-glucopyranoside, (2 ' Hexadecyloxy-ethyl) 4-O- (β-D-galactopyranosyl) -α-D-glucopyranoside, (2'-dodecyloxyethyl) 4-O- (α-D-glucopyranosyl) -α-D-glucopyranoside, ( 2'-tetradecyloxy-ethyl) 4-O- (α-D-glucopyranosyl) -α-D-glucopyranoside, (2'-hexadecyloxy-ethyl) -4-O- (α-D-glucopyranosyl) -α-D-glucopyranoside .

465 (2'-Dodecyloxy-ethyl) 6-O- (α-D-galactopyranosyl) -α-D-glucopyranoside, (2'-tetradecyloxy-ethyl) 6-O- (α-D-galactopyranosyl) -α-D glucopyranoside, (2'-hexadecyloxyethyl) 6-O- (α-D-galactopyranosyl) -α-D-glucopyranoside, (2'-dodecyloxyethyl) 4-O- (β-D-glucopyranosyl) -α -D-glucopyranoside, (2'-dodecyloxypropyl) -4-0- (α-D-glucopyranosyl) -α-D-glucopyranoside, (2'-dodecyloxypropyl) 6-O- (α-D-galactopyranosyl) -α-D-glucopyranoside,

470 1 -0- (Dodecyloxy) -3-0- (4'-O- (β-D-galactopyranosyl) -β-D-glucopyranosyl) -glycerol, 1-O- (Dodecyloxy) -2-0- (4 '-O- (β-D-galactopyranosyl) -β-D-glucopyranosyl) -glycerol, 1-O- (dodecyloxy) -3-0- (4'-O- (β-D-galactopyranosyl) -α-D glucopyranosyl) glycerol, 1-O- (dodecyloxy) -2-0- (4'-O- (β-D-galactopyranosyl) -α-D-glucopyranosyl) -glycerol, 1-O- (dodecyloxy) -3 -0- (4'-O- (α-D-glucopyranosyl) -β-D-glucopyranosyl) -glycerol, 1-O-

475 (dodecyloxy) -2-0- (4'-O- (α-D-glucopyranosyl) -β-D-glucopyranosyl) -glycerol, 1-0- (dodecyloxy) -3-O- (4'-O-) (α-D-glucopyranosyl) -α-D-glucopyranosyl) -glycerol, 1-0- (dodecyloxy) -2-O- (4'-O- (α-D-glucopyranosyl) -α-D-glucopyranosyl) - glycerol, (2 '- (2 "-dodecyloxyethyloxy) ethyl) 4-O- (β-D-galactopyranosyl) -β-D-glucopyranoside, (2' - (2" - (2 '"- dodecyloxyethyloxy) -ethyloxy ) -ethyl) 4-O- (β-D-galactopyranosyl) -β-D-glucopyranoside,

480 (2 '- (2 "- (2''' - (2 '''- dodecyloxyethyloxy) ethyloxy) ethyloxy) ethyl) 4-O- (β-D- galactopyranosyl) -β-D-glucopyranoside, (2 '- (2 "-dodecyloxyethyloxy) -ethyl) 4-O- (β-D-galactopyranosyl) -α-D-glucopyranoside, (2' - (2" - (2 '' -Dodecyloxyethyloxy) -ethyloxy) -ethyl) 4-O- (β-D-galactopyranosyl) -α-D-glucopyranoside, (2 '- (2' - (2 '' - (2 '' - dodecyloxyethyloxy) - ethyloxy) -ethyloxy) -ethyl) 4-O- (β-D-galactopyranosyl) -α-D-glucopyranoside, 1 -O-

485 (ethylhexyl) -3-0- (4'-O- (α-D-glucopyranosyl) -β-D-glucopyranosyl) -glycerol, 1 -O- (ethylhexyl) -2-0- (4'-O) (α-D-glucopyranosyl) -β-D-glucopyranosyl) glycerol, 1-O- (ethylhexyl) -3-0- (4'-O- (α-D-glucopyranosyl) -α-D-glucopyranosyl) - glycerol, 1 -O- (ethylhexyl) -2-0- (4'-O- (α-D-glucopyranosyl) -α-D-glucopyranosyl) -glycerol, 1-O- (ethylhexyl) -3-O- ( 4'-O- (β-D-galactopyranosyl) -β-D-glucopyranosyl) -glycerol, 1-O-

490 (ethylhexyl) -2-0- (4'-O- (β-D-galactopyranosyl) -β-D-glucopyranosyl) -glycerol, 1 -O- (ethylhexyl) -3-0- (4'-O-) (β-D-galactopyranosyl) -α-D-glucopyranosyl) -glycerol, 1-O- (ethylhexyl) -2-0- (4'-O- (β-D-galactopyranosyl) -α-D-glucopyranosyl) - glycerol. According to the invention, a surfactant or emulsifier system is also composed of (a) alkyl ether sulfate, for example sodium, ammonium, magnesium, MIPA, TIPA,

495 rethsulfate, sodium myreth sulfate and sodium C ₁₂ .i ₃ -pareth sulfate, (b) alkyl sulfates, for example sodium, ammonium and TEA lauryl sulfate, (c) sodium alkyl sulfates such as sodium cetearyl sulfate and at least one compound according to the invention, particularly preferably from lauryl ether sulfate. and / or lauryl sulfate and at least one compound of the invention.

500 According to the invention is also a cosmetic preparation such as shampoo, hair conditioner, styling agent, dentifrice, shower gel, shower foam, bath foam, Syndetstück, hair dye, facial cleanser, liquid hand detergent, liquid soap, shaving aid (gel or foam), make-up remover, impregnation medium for wipes and / or tissue containing a compound of the invention or

505 containing a surfactant system according to the invention.

According to the invention is also a cleaning agent for the household or for technical purposes such as household cleaners, window cleaners, liquid detergents for textiles, washing powder for textiles, Textilwaschpulveragglomerat or -pellet, machine dishwashing detergents, hand dishwashing detergents containing an inventive

510 compound or containing a surfactant system according to the invention.

The invention also provides a food preparation such as beer, drink, food, tofu containing a compound according to the invention or containing a surfactant system according to the invention. Also according to the invention is a foam-like or foamable preparation

515, a compound according to the invention or containing a surfactant system according to the invention.

In all the preparations according to the invention it is particularly preferred if the use concentration of the compound according to the invention is 0.3 to 25% by weight. According to the invention is also a use of a compound of the invention or

520 of a surfactant system according to the invention as detergent or cosurfactant in a household cleaner, window cleaner, laundry detergent for textiles, washing powder for textiles, textile washing powder agglomerate or pellet, machine dishwashing detergent, hand dishwashing detergent, hair shampoo, hair conditioner, styling agent, dentifrice, shower gel, shower foam, bath foam, syndet, hair dye,

525 Cream, lotion, facial cleanser, liquid hand wash, liquid soap, shaving aid (gel or foam), make-up remover, impregnation medium for tissues and / or tissues. The invention also provides a use of a compound of the invention or of a surfactant system according to the invention for the preparation of a medicament.

530 According to the invention is also a use of a compound according to the invention or of a surfactant system according to the invention for improving the foamability of a water-containing preparation.

Surfactant or emulsifier systems according to the invention may additionally contain alkylamidopropylbetaines (for example cocamidopropylbetaine), cocoamphoacetate, lauryl ether sulphate,

535 fatty acid salts, sarcosinates, acylglutamates, acyl lactylates, acyl isethionates, sulfosuccinates containing.

Compositions according to the invention can additionally comprise polymers, where the polymer (s) can be nonionic, cationic, anionic or amphoteric. The invention also encompasses the use of ((2'-dodecyloxyethyl) 4-O- (β-D-)

540 galactopyranosyl) -β-D-glucopyranoside) and / or ((2'-dodecyloxypropyl) 4-O- (β-D-galactopyranosyl) -β-D-glucopyranoside) as gelling agents and / or as foaming agents for aqueous systems ,

The invention also encompasses a process for preparing a compound of the invention by reacting a β-peracetate of component A with a Lewis

545 acid and the polyol ether A _x -B.

The invention also encompasses the preparation of the compounds according to the invention by reacting a β-peracetate with boron trifluoride-diethyl ether complex as Lewis acid, 2Ü

according to Example 1, particularly preferably with an α-peracetate and an extended one

Reaction time. 550 The invention also encompasses a process for the preparation of a novel composition

Compound according to one of the preceding claims by trans glycosylation of butyl glycosides, propyl glycosides, ethyl glycosides, methyl glycosides with

Polyolethem A _x -B.

The invention also encompasses the preparation of the compounds according to the invention by way of direct Fischer glycosylation and the preparation of the compounds according to the invention from glycosyl halides, from glycosylimidates,

Orthoestheses, n-pentenyl glycosides, thioglycosides, allyl glycosides, and the like. known

Precursors.

The invention also includes laureth-2-lactoside, laureth-3-lactoside, laureth-2-maltoside, 560 laureth-3-maltoside as well as products of the reaction of a disaccharide with a

Glycerol ethers and / or a diglycerol ether and / or a triglycerol ether, the

Reaction of lactose with ethylhexylglycerol, the reaction of lactose with

Laurylglycerinether, the reaction of maltose with ethylhexylglycerol and the

Reaction of maltose with lauryl glycerol ether. 565 Components according to the invention may furthermore contain surfactants.

A. Anionic surfactants

Advantageously used anionic surfactants are: acylamino acids (and their salts), such as

570 1. acylglutamates, for example, disodium acylglutamate, sodium acylglutamate and sodium caprylic / capric glutamate,

2. Acyl peptides, for example palmitoyl-hydrolyzed milk protein, sodium cocoyl-hydrolysed soy protein and sodium / potassium cocoyl-hydrolyzed collagen, N-cocoyl-hydrolyzed wheat protein, N-cocoyl

575 hydrolyzed amino acids,

3. sarcosinates, for example myristoyl sarcosine, TEA-lauroyl sarcosinate, sodium lauroyl sarcosinate and sodium cocoyl sarcosinate,

4. taurates, for example sodium lauroyl taurate and sodium methyl cocoyl taurate,

5. acyl lactylates, for example, lauroyl lactylate, caproyl lactylate, 580, 6-alaninates,

7. Arginates, for example N-lauroyl arginate, 8. valinates, for example N-lauroyl valinate,

9. Prolinates, for example N-lauroyl prolinate,

10. Glycinate, for example N-lauroyl glycinate, cocoamphopolycarboxyglycinate, 585 11. Aspartates, for example N-lauroyl aspartates, di-TEA-palmitoyl aspartate,

Carboxylic acids and derivatives, such as

1. Carboxylic acids and their alkali and alkaline earth salts, triethanolamine salts, or zinc salts, for example lauric acid, sodium, potassium, magnesium

590 alkoxide and zinc undecylenate,

2. Ester carboxylic acids, for example calcium stearoyl lactylate, laureth-6-citrate and sodium PEG-4-lauramide carboxylate,

3. Ether carboxylic acids, for example sodium laureth-13-carboxylate and sodium PEG-6-cocamide carboxylate,

595 4th sodium PEG-7 olive oil carboxylate,

Phosphoric acid esters and salts, such as, for example, DEA-oleth-10-phosphate and dilaureth-4-phosphate,

600 sulfonic acids and salts, such as

1. Acyl-isethionates, e.g. Sodium / ammonium cocoylisethionate,

2. alkylaryl sulphonates,

3. alkylsulfonates, for example Natriumcocosmoπoglyceridsulfat, sodium _C-12 olefin sulfonate _14, sodium lauryl sulfoacetate and magnesium PEG-3

605 cocamide sulphate,

4. Sulfosuccinates, for example dioctyl sodium sulphosuccinate, disodium laureth sulphosuccinate, disodium lauryl sulphosuccinate and disodium undecylenamido MEA sulphosuccinate, and also 610 sulfuric acid esters, such as

1. alkyl ether sulfate, for example sodium, ammonium, magnesium,

MIPA, TIPA laureth sulfate, sodium myreth sulfate, and sodium C ₁₂ -i ₃ - pareth sulfate,

2. Alkyl sulfates, for example sodium, ammonium and TEA lauryl sulfate, 615 3. Sodium alkyl sulfates such as sodium cetearyl sulfate. B. Cationic surfactants

Advantageously used cationic surfactants are:

1. alkylamines,

2. alkylimidazoles,

620 3. Ethoxylated amines and

4. Quaternary surfactants.

5. Esterquats

Quaternary surfactants contain at least one N-atom, which with 4 alkyl and / or

625 aryl groups is covalently linked. This results in a positive charge regardless of the pH. Advantageous quaternary surfactants are alkyl betaine, alkyl amido propyl betaine and alkyl amidopropyl hydroxysulfain. Cationic surfactants can furthermore preferably be selected for the purposes of the present invention from the group of the quaternary ammonium compounds, in particular

630 cyclic alkylammonium chlorides or bromides, such as, for example, benzyldimethylstearylammonium chloride, furthermore alkylthalkylammonium salts, for example cetyltrimethylammonium chloride or bromide, alkyldimethylhydroxyethylammonium chlorides or bromides, dialkyldimethylammonium chlorides or bromides, dialkyl ethoxylate dimethylammonium chlorides or bromides such as, for example,

635 C18) alkyl (EO) 3-20 dimethylammonium salts or distearyl (EO) 5-dimethyl ammonium chloride and distearyl (EO) 15 dimethyl ammonium chloride. Alkylamidethyltrimethylammonium ether sulfates, alkylpyridinium salts, for example lauryl or cetylpyrimidinium chloride, imidazoline derivatives and compounds having a cationic character, such as amine oxides, for example alkyldimethylamine oxides or alkylamino

640 ethyldimethylamine oxides. Cetyltrimethylammonium salts are particularly advantageous to use.

C. Amphoteric surfactants

Advantageous amphoteric surfactants to be used are:

645 1. acyldialkylethylenediamine, for example sodium acylamphoacetate, disodium acylamphodipropionate, disodium alkylamphodiacetate,

Sodium acylamphohydroxypropylsulfonate, disodium acylamphodiacetate and sodium acylamphopropionate, 2. N-alkylamino acids, for example aminopropylalkylglutamide, alkylamino-650-propionic acid, sodium alkylimidodipropionate and lauroamphocarboxyglycinate.

Furthermore, it is also possible to add cationic polymers to preparations according to the invention. These improve the feeling on the skin and can advantageously influence the foam behavior of the formulations according to the invention. 655

Cationic polymers

1. Quaternary derivatives of cellulose ethers.

For example, Polyquaternium 10, Polyquaterπium 24 is preferred.

2. Quaternary derivatives of gums.

660 Preferably, for example, guar hydroxypropyltrimonium chloride and

Hydroxypropyltrimonium hydroxypropyl guar.

3. Homopolymers and Copolymers of Dimethyl Diallyammonium Chloride (DMDAAC).

For example, polyquaternium 4 and 6 and 7 are preferred.

665 4. Homopolymers and copolymers of methacrylamidopropyl trimethyl ammonium chloride (MAPTAC).

Polyquaternium 28 and polymethacrylamidopropyltrimonium chloride, for example, are preferred.

5. Homopolymers and copolymers of acrylamidopropyl trimethyl ammonium 670 chloride (APTAC).

6. Homopolymers and copolymers of methacryloyloxy ethyl trimethyl ammonium. chloride (METAC).

Preference is given, for example, to Polyquaternium 32 and Polyquaternium 37.

7. Homopolymers and copolymers of acryloyloxy ethyl trimethyl ammonium 675 chloride (AETAC).

For example, polyquaternium 33 is preferred.

8. Homopolymers and copolymers of methacryloyloxy ethyl trimethyl ammonium methyl sulfate (METAMS).

For example, polyquaternium 5 and polyquaternium 11 and 680 polyquaternium 14 and polyquaternium 15 and polyquaternium 36 and are preferred

Polyquaternium 45.

9. Homopolymers and Copolymers of Vinylpyrrolidone. For example, Luviquat 905 is preferred.

10. Cationic polysaccharides,

685 based on hydroxyalkylcelluloses, starches, hydroxyalkyl starches, polymers based on arabinose monomers, polymers derived from xylose, fucose, fructose, galacturonic acid and glucuronic acid, galactosamine and glucosamine, acetylglucosamine, galactose, mannose. For example, hydroxypropyl trimethyl ammonium chloride are preferred

690 derivatives of starch, which may be from corn, potato, rice, tapioaca, wheat and the like.

11. Ammonium substituted polydimethylsiloxanes.

Preferred are, for example, trimethylsilylamodimethicone (Dow Corning Q2-8220), copolymers of polydimethylsiloxane and poly (C2-C3) alkylene ether (Dow 695 Corning 190, Dow Corning 2-5324, Dow Corning Q2-5220), Abil-Quat 3270.

12. PVP.

13. Polyethyleneimines.

Preference is given, for example, to Lupasol FG (BASF), Lupasol G-35 (BASF), Lupasol P (BASF). 700. 14. Chitosan.

15. Gellan gum.

16. Polymers of ethylene glycol (PEG-150 distearate).

17. Block copolymers (PEG / PPG).

18. Celluloses (hydroxyethylcellulose, cetylhydroxyethylcellulose,

705 hydroxypropylmethylcellulose, sodium carboxymethylcellulose, etc.).

19. Polyacrylic acid and derivatives, acrylic acid copolymers and derivatives, alkyl acrylates, carbopols.

20. Carragenans and derivatives. Hyaluronic acid and derivatives.

710

Compositions according to the present invention may also contain moisturizers such as glycerine, chitosan, fucogel, lactic acid, propylene glycol, dipropylene glycol, butylene glycol, mannitol, sodium pyrollocarboxylic acid, hyaluronic acid and its salts, amino acids such as glycine, urea, sodium and potassium salts.

715 Furthermore, it is also advantageous to use salts for the alkyl glycosides according to the invention. Particularly advantageous are calcium chloride, magnesium sulfate, sodium sulfate, KCl, magnesium chloride and sodium chloride. It is also particularly advantageous to add water-soluble active ingredients.

720

synthesis

The preparation processes for components according to the invention are basically known (ViII, V., Böcker, T., Thiem, J., Fischer, F., Liq. Cryst., 6, 1989, 349 et seq., V. Minden, HM, Brandenburg , K., Seydel, U., Koch, MHJ, Garamus, VM, Willumeit, R., ViII, V.

725 Chem. Phys. Lipids, 106, 2000, 157ff.). These provide the product in the highest purity and only one anomer after purification by column chromatography. The yield is, in the case of Laurylethylenglycolglycoside, between 30 and 45%. Deviating from this, it was found that a longer reaction time (18 hours instead of 5 hours) in the case of the ethylene glycol and propylene glycol ethers leads to significantly higher yields. The

730 desired products could be obtained in yields of 50-60%, while an increase in the proportion of α-anomer was not observed. However, the workup can be simplified, a column chromatography is then no longer necessary. The reaction is stopped after the desired time by neutralization as described above. Salts are washed out with water and the reaction mixture becomes

735 then stirred to remove the protecting groups in basic medium at pH 8-9 (NaOMe in MeOH). After neutralization with acidic ion exchanger, the solvent is removed. Unreacted alcohol is washed out with nonpolar solvent (e.g., petroleum ether 50-70), unreacted sugar is precipitated with polar solvent (e.g., ethanol). The batch size can be chosen much larger. The way

740 describe the β-anomer. The representation of the α-anomer can be carried out similarly only as Lewis acid stannic chloride used in equimolar amount and the reaction time increases to at least 48 hours, the yield is in the case of Laurylethylenglycolglycoside between 25 and 30%. The use of polyhydric alcohols or mixtures of alcohols leads to

745 product mixtures that can not be separated according to the procedures described. However, this is unnecessary in view of the fact that the formation of mixtures is quite desirable and leads to an improved solubility in water. The reaction of maltose peracetate with 1-ethylhexyl glycerol gives the maltoside as a mixture of the 1, 3 and and 1, 2-substituted derivatives of glycerol in one 750 total yield of 44%. Also, the reaction of Laureth-2 (Sasol) with lactose peracetate is easily possible. This gives a mixture of the products, due to the inhomogeneous composition of the alcohol used. The preparation of the compounds is also possible in other known ways. Thus, the use of the above-mentioned Lewis acids is not mandatory, there may be others

755 suitable for glycosylations Lewis acids (eg TMS triflate) can be used. Furthermore, glycosylation with the α-peracetate or a mixture of the α- and β-peracetate of the sugar is possible, it then extends according to the reaction time. The preparation of the glycosyl halides of sugar is also possible, also on

760 other ways than the classical King Knorr synthesis. It is also possible to prepare the compounds by reacting previously prepared glycosylimidates, thioglycosides, n-pentenyl glycosides, allyl glycosides and similar activated sugars.

765 Of technical importance is the direct conversion of the unprotected sugar with the alcohol under acid catalysis in the so-called Fischer glycosylation.

Here, because of the better yields, the variant of the transglycosylation of the

Butyl, propyl, ethyl or methyl glycosides to be preferred.

Reaction of a short chain glycoside provides the desired products under milder reaction conditions 770.

775

780 Examples

Preparation of surfactants (lactosides)

The lactosides are α / ß mixtures. The following lactosides were prepared 785:

example 1

Preparation of Lac-EG-C12

790 6.8 g (10 mmol) of lactose peracetate and 2.40 g (11 mmol) of 2-dodecyloxyethanol are dissolved in 100 mL of anhydrous dichloromethane under a nitrogen atmosphere. 1.99 g (1.76 mL, 14 mmol) of boron trifluoride diethyl etherate are added dropwise and the solution is stirred for 5 hours at room temperature. After complete reaction (TLC) is neutralized with 50 mL of saturated sodium bicarbonate solution. The organic phase becomes

795 separated and the aqueous extracted twice with dichloromethane. The combined organic phases are washed twice with water. After drying over magnesium sulfate, the solvent is removed under reduced pressure. The residue is purified by column chromatography (petroleum ether 50-70 / ethyl acetate 1: 1) and gives the β-product in good yields. The acetylated compound is in

Dissolved 800 anhydrous methanol and treated with sodium methoxide (pH 8-9). Thereafter, it is stirred at room temperature until complete reaction (TLC). The solution is mixed with ion exchanger (Amberlyts IR 120, H ⁺ form), filtered and the solvent removed in vacuo. Yield: 1.6 g, corresponding to 29% of theory

805 Example 2

Preparation of Lac-PG-C12

Lactose peracetate and dodecyloxypropan-1-ol are reacted as described in Example 1, except that the reaction time is 18 hours. It is then neutralized and the solution is concentrated to dryness. The 810 residue is deprotected as described in Example 1 and the β-product is purified by column chromatography (chloroform / methanol 3: 1). Yield: 3.2 g, corresponding to 58% of theory Example 3 815 Preparation of MaI-EG-CI 2

6.8 g (10 mmol) of maltose peracetate and 1.1 eq. (2.4 g, mmol) of 2-dodecyloxyethanol are reacted as described in Example 2, with the exception that the compound is first deprotected and then the β-product is purified by column chromatography (chloroform / methanol 3: 1). Yield: 3.3 g, corresponding to 60% of theory

820

Example 4

Preparation of Lac-PG-C12

34 g (50 mmol) lactose peracetate, 1.1 eq. (13.4 g, 55 mmol) 3-dodecyloxypropan-1-ol,

1.4 eq. (9.9 g, 8.8 mL, 70 mmol) boron trifluoride diethyl ether complex are dissolved in 300 mL

825 anhydrous dichloromethane as described in Example 2, with the exception that a column chromatographic purification is dispensed with. Instead, unreacted alcohol is washed out with petroleum ether (50-70), the remaining residue is then taken up in ethanol and unreacted lactose is filtered off. The solvent is removed in vacuo. You get that

830 product as a mixture of the two anomers. Yield: 16.6 g, corresponding to 60% of theory

Example 5

Preparation of Lac-Laureth-2

34 g (50 mmol) lactose peracetate and 20 mL laureth-II (Marlipal 24/20, Sasol)

835 are reacted as described in Example 4. The product is a mixture of the α- and β-anomers where the β-portion predominates. The product distribution depends on the used

Alcohol off. Typically, a mixture of lactosides of lauryl / myristyl is obtained

Ethylene glycols, lauryl / myristyl diethylene glycols, lauryl / myristyl triethylene glycols and higher ethoxylated adducts, wherein the proportion of diethoxylierten prevails. Yield: 25

840 g.

Example 6

Production of MaI-EHG

6.8 g (10 mmol) of maltose peracetate and 4.1 g (4.3 mL, 20 mmol) of (2-ethylhexyl) -glycerol 845 (Sensiva SC50, Schülke & Mayr) are reacted as described in Example 1. Yield: 2.3 g, corresponding to 44% of theory Example 7

Preparation of Lac-α-EG-C12

850 6.8 g (10 mmol) lactose peracetate and 1.1 eq. (2.54 g, 1 1 mmol) of 2-dodecyloxyethanol are dissolved under nitrogen atmosphere in 100 ml of anhydrous dichloromethane. 10 mmol (2.6 g, 1.14 ml) tin tetrachloride are within 30 min. dropwise. The solution is then stirred for 72 hours at room temperature. The reaction is stopped by adding saturated sodium bicarbonate solution and the

855 organic phase is separated. The aqueous phase is extracted once with dichloromethane. The combined organic phases are washed with water, dried over magnesium sulfate and the solvent removed under reduced pressure. The residue is taken up in 50 ml of anhydrous methanol and deprotected as described in Example 1. The α-anomer becomes after column chromatographic separation

860 (chloroform / methanol 3: 1). Yield: 1.7 g, corresponding to 30% of theory

Examples 7a

General procedure for the preparation of octaacetyl-β-lactose:

865 Preparation of 1,2,3,4-tetra-O-acetyl-4-O- (2 ^' , 3 ^' , 4 ^' , 5 ^' -tetra-O-acetyl-β-D-galactopyranosyl) -β-D-glucopyranoside ; (Octaacetyl-.beta.-lactose) Lac-OAc (.beta.-anomer)

40.0 g (0.117 mol) of anhydrous lactose (or lactose monohydrate) were dissolved in 1 10 mL (1.17 mol) of acetic anhydride. The mixture was cooled to -5 ⁰ C and it

In 870, a mixture of 4 drops of concentrated sulfuric acid in 1 mL of acetic anhydride was added slowly and dropwise. After completion of the addition was stirred for 10 minutes at -5 ° C, then stirred for 2 hours at 60 ° C. The solution was poured onto ice and treated with dichloromethane. The phases were separated and the aqueous phase was extracted twice with 50 mL dichloromethane.

875 The combined organic phases were added dropwise to 600 mL of saturated sodium bicarbonate solution. The solution was filtered to remove the excess solid sodium hydrogen carbonate. The aqueous phase was extracted twice with 50 mL dichloromethane. The combined organic phases were washed with 100 mL H ₂ O, dried over MgSO ₄ and the solvent was concentrated under reduced pressure

880 pressure removed.

The product was recrystallized in freshly distilled ethanol. General instructions Lactosides from fatty alcohol ethoxylates and lactose: [Lutensol ^® ON 30 (C10-alcohol +3 EO); Berol 260 (C9-C11 alcohol ethoxylate (4)); Berol 532 (C11 alcohol ethoxylate (2)); Berol 533 (C11 alcohol ethoxylate (3))]:

885

6.8 g (10 mmol) 1, 2,3,4-tetra-O-acetyl-4-O- (2 ^', ^3', 4 ^', ^5' tetra-O-acetyl-ß-D-galactopyranosyl) - ß-D-glucopyranoside and (14 mmol) of the corresponding alcohol ethoxylate [Lutensol ON 30 ^® (C10-alcohol + 3 EO); Berol 260 (C9-C11 alcohol ethoxylate (4)); or Berol 532 (C1 1 alcohol ethoxylate (2)); Berol 533 (C11 alcohol ethoxylate (3))] in 10O mL

890 abs. Dichloromethane was dissolved with stirring. For this purpose, 1.99 g (14 mmol) of boron trifluoride etherate were slowly added dropwise. Subsequently, the reaction mixture was stirred overnight at room temperature. For working up the product, 100 ml of saturated sodium bicarbonate solution were added and the mixture was stirred for a further 30 min. touched. The aqueous phase was extracted twice with 30 mL each of dichloromethane, the

895 combined organic phases were washed twice with 60 mL of saturated sodium bicarbonate solution and once with 60 mL of distilled water. After subsequent drying over magnesium sulfate, the solvent was removed under reduced pressure. The product was purified by column chromatography (petroleum ether (50-70), ethyl acetate 2: 1).

900

DC:

Eluent (petroleum ether (50-70), ethyl acetate 1/1). ^'

The peracetylated lactosides were each treated with about 8O mL of anhydrous methanol and

905 3 Spatelspitzen Natiummethylat (pH test (pH: 10)) stirred for three hours. The

Solutions were stirred for about 15 minutes after addition of Dowex 50 WX 4 ion exchanger. After a subsequent pH test (pH: 4), the ion exchanger was filtered off and the solvent was removed under reduced pressure. The products were purified by column chromatography (chloroform, methanol 3: 1). The products are for

910 part α / ß mixtures.

The following products 13 to 16 were produced according to the general work instruction just mentioned:

915 Product 13.)

(2- [2- [2- (Decyloxy) ethoxy] ethoxy] ethyl) -4-O- (β-D-galactopyranosyl) -β-D-glucopyranoside 920 (LaC-EG ₃ CIO), and

(2- [2- [2- (decyloxy) ethoxy] ethoxy] ethyl) -4-O- (β-D-galactopyranosyl) -α-D-glucopyranoside (Lac-α-EG ₃ C10),

925 Implementation of Lutensol ^® ON 30 with lactose

The Lutensol ^® ON 30 (C10-alcohol +3 EO) was purchased from BASF Ludwigshafen, 67056 Germany. A mixture of Lac-EG ₃ C10 and Lac-α-EG ₃ CIO 930 is obtained

Product 14.1

(2- [2- [2- [2- (Nonyloxy) ethoxy] ethoxy] ethoxy) ethyl) -4-0- (β-D-galactopyranosyl) -β-D-935 glucopyranoside (Lac-EG ₄ C9)

(2- [2- [2- (Nonyloxy) ethoxy] ethoxy] ethoxy) ethyl) -4-0- (β-D-galactopyranosyl) -α-D-glucopyranoside 940 (Lac-σ-EG ₄ C9)

(2- [2- [2- [2- (Decyloxy) ethoxy] ethoxy] ethoxy)] ethyl) -4-O- (β-D-galactopyranosyl) -β-D-glucopyranoside

(LaC-EC ₄ CIO)

945

(2- [2- [2- [2- (Decyloxy) ethoxy] ethoxy] ethoxy)] ethyl) -4-O- (β-D-galactopyranosyl) -α-D-glucopyranoside

(Lac-α-EG ₄ C10)

950

(2- [2- [2- [2- (undecyloxy) ethoxy] ethoxy] ethoxy)] ethyl) -4-O- (β-D-galactopyranosyl) -β-D-glucopyranoside

Lac-EC ₄ C11

955 (2- [2- [2- [2- (undecyloxy) ethoxy] ethoxy] ethoxy)] ethyl) -4-O- (β-D-galactopyranosyl) -α-D-glucopyranoside

(Lac-α-ECCH)

960

Lactoside: Lac-EG ₄ C9 and Lac-α-EG ₄ C9 Lactoside: Lac-EG ₄ C10 and Lac-α-EG ₄ C10 Lactoside: Lac-EG ₄ C11 and Lac-α-EG ₄ C11 965

Implementation of Berol 260 (Akzo) with lactose

The Berol 260 (C11 Alcohol Ethoxylate (4) was obtained from Akzo Nobel Surface Chemistry AB SE 44485 Stenungsund, Sweden, Mainly a 970 blend of Lac-EG ₄ C 9, Lac-α-EG ₄ C 9, Lac-EG ₄ C10, Lac-α-EG ₄ C10, Lac-EG ₄ C11 and Lac-α-EG ₄ C11.

Product 15.)

975 Lactoside: Lac-EG ₂ -C11 and Lac-α-EG ₂ -C11

(2- [2- (N -decyloxy) ethoxy] ethyl) -4-0- (β-D-galactopyranosyl) -β-D-glucopyranoside (Lac-EG ₂ C11) 980

(2- [2- (Undecyloxy) ethoxy] ethyl) -4-O- (β-D-galactopyranosyl) -α-D-glucopyranoside (Lac-α-EG ₂ C11)

Reaction of Berol 532 with lactose.

985

The Berol 532 (C11 alcohol ethoxylate (2)) was purchased from Akzo Nobel Surface Chemistry AB SE 44485 Stenungsund, Sweden. Mainly a mixture of Lac-EG ₂ -C11 and Lac-α-EG ₂ -C 11 is obtained.

990 product 16.)

Lactoside: Lac-EG ₃ -C11 and Lac-α-EG ₃ -C11

995 (2- [2- [2- (undecyloxy) ethoxy] ethoxy] ethyl) -4-0- (β-D-galactopyranosyl) -β-D-glucopyranoside (LaC-EG ₃ CH) (2- [2- [2- (Undecyloxy) ethoxy] ethoxy] ethyl) -4-O- (β-D-galactopyranosyl) -α-D-1000 glucopyranoside (Lac-α-EG ₃ C11)

Reaction of Berol 533 (C11 alcohol ethoxylate (3)) with lactose

1005 The Berol 533 (C11 alcohol ethoxylate (3)) was purchased from Akzo Nobel Surface Chemistry AB SE 44485 Stenungsund, Sweden. Mainly a mixture of Lac-EG ₃ -C11 and Lac-α-EG ₃ -C 11 is obtained.

Dr + nl_mi7R Quick test to investigate the foaming behavior:

1010 The measurements were carried out in 5 ml specimen jars. Solutions are prepared by weighing 0.05 g of surfactant and adding 0.95 g of distilled water to a total weight of 1 g (about 1 mL). To foam, the test tube is shaken 20 times within 10 sec. The foam volumes are immediately after shaking the specimen jars (foaming power) and after 20 minutes

1015 (foam stability).

Figure 1 shows the foam immediately after shaking. Shown are lactosides from lactose and corresponding ethoxylated fatty alcohol. Here, 1) Lutensol ON 30 ^® (CIO alcohol +3 EO), 2.) Berol 533 (C1 1 alcohol ethoxylate (3)), 3.) Berol 260 (C9-C11 alcohol ethoxylate 1020 (4)); 4. ) Berol 532 (C 11 Alcohol ethoxylate (2))

Figure 2 shows the foam after 20 minutes. Shown are lactosides from lactose and corresponding ethoxylated fatty alcohol. 1.) Lutensol ON 30 ^® (C10-alcohol + 3 EO), 2.) Berol 533 (C11 alcohol ethoxylate (3)), 3.) Berol 260 (C9-C11 alcohol ethoxylate 1025 (4)), 4.) Berol 532 (C1 1 alcohol ethoxylate (2))

Results:

1030 The lactosides 1-4 show very good foaming properties at this concentration. The foaming power is very good in all. The foam is optically fine-pored. After 20 minutes, hardly any changes in the foam pattern, this indicates a pronounced foam stability.

1035 materials:

The starting materials used were the following substances:

The disaccharide used was the lactose monohydrate Variolac 99 edible G800 from Biolac GmbH & Co. KG, 31097 Harbamsen.

1040 Lactose monohydrate or anhydrous lactose can be used to prepare the compounds. Gel formation by surfactants according to the invention:

1045 The gelation of the laurylglycol compounds Lac-EG-C12 and Lac-PG-C12 is unusual in that the compounds according to the invention have no structure normally customary for gelling agents. Accordingly, gel formation is highly dependent on the ratio between the hydrophilic and hydrophobic moieties. The use of a spacer when connecting Lac-EG-C12

1050 ethylene glycol and in the case of Lac-PG-12 propylene glycol, leads to the formation of a stable gel.

Particularly advantageous are the substances Lac-EG-C12 and Lac-PG-C12. Thus, for example, Lac-EG-C12 forms a gel at a concentration of 0.1% by weight up to a transition temperature of 43 ^° C. and Lac-PG-C12 at 0.1% by weight to 41 ^° C. Above this transition temperature, the gel becomes liquid. The structure Lac-EG-C12 is above

1055 also particularly advantageous as a gelling agent, since the gel is mechanically stable. A more detailed list of transition temperatures at various concentrations can be found in Example 1 and Figure 2. Interesting for medical applications is gel formation in mixtures of water and dimethylsulfoxide (DMSO). Again, the compound Lac-EG-C12 proves to be particularly advantageous. The

1060 gelation behavior is exemplified for a concentration of 0.1% by weight in Table 2.

Furthermore, it has been found that Lac-EG-C12 can also be used in mixtures with other surfactants, e.g. Lauryl ether sulfate and cosurfactants, e.g. Cocoamphoacetate, cocamidoproyl betaine, cocoylglutamate is able to form gels.

1065

A person skilled in the art knows that the viscosity is increased in conventional lauryl ether sulfate-based surfactant system by addition of high concentrations of common salt or by addition of water-soluble polymers or both. Furthermore, pure surfactant formulations containing APGs are free of

1070 anionic surfactants such as lauryl ether sulfate, thickeners are added because APGs in low concentrations have no thickening effect. Example 8

Gelation of Lac-EG-C12 in water

1075 Table 1: Phase transition temperatures (T _ge ι) from the gel to the isotropic solution for different concentrations of lipid (deviation ± 0.5 ⁰ C). The compound forms a stable gel and above T _ge ι a clear solution. T _ge ι is defined as the temperature at which the gel begins to dissolve. The temperature range of the transition is normally 2 to 5 ⁰ C.

1080

Concentration concentration Tgel

Wt.% MM [ ⁰ C]

10 180.40 51

5 90.20 51

1 18.04 50

0.5 9.02 48

0.2 3.61 46

0.13 2.41 45

0.1 1.80 43

0.08 1.44 40

0.07 1.20 38

0.06 1.03 35

0.05 0.90 30

0.04 0.72 21

0.03 0 60 10

Phase diagram of the compound Lac-EG-C12 in water,

1085 (see Fig. 1)

Example 8a

The lactoside from Berol 260 and lactose (product 14)) is capable of gelation. The resulting gel is exceptionally clear, for example, at a level of 5% by weight in water 1090. See Figure 3.

Example 9

Gel Formation of Lac-EG-C12 in Dimethylsulfoxide (DMSO) / Water - Mixtures 1095 Table 2: Phase transition temperatures (T _ge ) from gel to isotropic solution for different solvent composition (dimethyl sulfoxide, DMSO and water,

H ₂ O) with a constant lipid concentration (0.1 wt.%) (Deviation ± 0.5 ⁰ C). The

Compound forms clear gels or gels only partially, above the

Transition temperature makes them a clear solution. T _ge ι is defined as the temperature at 1100 which the gel begins to dissolve. The temperature range of the transition is in

Normal case 2 to 5 ⁰ C.

G = GeI

G _p = partially gelled

I = isotropic solution 1105 S = solid on cooling (due to frozen solvent)

Surfactants / surfactant mixtures without gelation

Gel formation can also be reversed by admixing other compounds. This can be achieved by using mono-, di- and triethylene glycol alkyl ethers

Lactoside mixes with each other.

The mixtures which are obtained by reacting laureth-2 or laureth-3 with lactose (Lac-Laureth-2 and Lac-Laureth-3) are particularly advantageous.

Furthermore, the α-anomer of Lac-EG-C12 is particularly preferred since it also does not form a gel. In addition, it has been found that, from a proportion of α-anomer in a concentration of more than 80% by weight, gelation by the β-anomeric lactone

EC-C12 is lifted. It was also observed that a mixture of 13% by weight.

Laurylethersulfat with 2 wt.% Of ß-anomer of Lac-EG-C12 no longer forms gel, but at a ratio of 11 wt.% Laurylethersulfat to 4 wt.% Of the ß-anomer of Lac-1120 EG-C12 gelation but again starts. In this way it is possible the

Gelation by the ratio (and the selection) of lactoside to control cosurfactant.

Foaming behavior of aqueous preparations with surfactants according to the invention

Some of the substances were examined by way of example for their foam properties in water 1125.

method

Measurements are carried out in 100 ml_ measuring cylinders. Before use, the measuring cylinder is filled with concentrated nitrating acid and stored for 24 hours, then with

1130 distilled water for a further 24 hours. Solutions are prepared by weighing the lipid and adding bidistilled water to a total weight of 10 g (about 10 mL). Solutions of the lower concentration are prepared by dilution of the first. Before the measurement, the measuring cylinder is stored at the desired temperature. To foam the measuring cylinder is 20 times

1135 within 30 seconds. The measurement is repeated up to a deviation of not more than 5%. Foam volumes are determined immediately after swirling the cylinder (foaming power) and after 30 minutes (foam stability). 1140 results

Very good foam properties compared to e.g. ionic surfactants (e.g.

Sodium lauryl ether sulfate, SLES or sodium lauryl sulfate, SDS) were determined, especially at higher temperatures, the foaming power and the stability of the foams is significantly better. 1145 When the concentration is reduced by a factor of 10, ionic surfactants are in fact no longer able to foam, whereas the lipids examined still show a pronounced foaming power.

Example 10

1150 Foaming power and foam stability of selected compounds at a surfactant concentration of 0.1 wt.%, And a temperature of 25 ⁰ C and 50 ⁰ C (Lac-EG-C12: lauryl ethylene glycol-ß-lactoside, MaI-EG-CI 2: Laurylethylenglycol-ß Maltoside, MeI-EG-CI 2: lauryl ethylene glycol β-melibioside, SDS: sodium dodecyl sulfate, SLES: lauryl ether sulfate).

1 155 See Figure 4.

Example 11

. Foamability and foam stability of selected compounds at a surfactant concentration of 0.01 wt% and a temperature of 25 ⁰ C and 50 ⁰ C (Lac- 1160 EC C12: Laurylethylenglycol-ß-lactoside, time-EC C12: Laurylethylenglycol-.beta. Maltoside, MeI-EG-CI 2: lauryl ethylene glycol β-melibioside, SDS: sodium dodecyl sulfate, SLES: lauryl ether sulfate). See Figure 5.

1165 Foaming behavior on hair

Another important property is the foaming power on skin or hair. The Ross Miles foam test data often can not be correlated with hair and skin foam.

Here, surprisingly, the compounds according to the invention showed a comparable foam formation on the skin or the hair, such as, for example, lauryl ether sulfate, but in significantly lower use concentrations. From the data for Lac-EG-C12 (Table 10), it was not necessarily expected that water in triturating the surfactant in hand would be a good foaming agent. Also in In the presence of hair, scum formation 1175 is observed when triturating the surfactant. For this purpose, 1% by weight of the substance according to the invention was dissolved in water in the presence of hair strands and rubbed in the hand.

The foam is much finer than comparable foams of lauryl ether sulfate. The best foaming agent in the form of its individual component according to the invention was the β-anomeric Lac-EG-C12 or also Lac-Laureth-2 or Lac-Laureth-3. 1180

However, the foaming behavior of the other surfactants according to the invention can be described in terms of foaming power and fine-poredness of the foam by adding classical cosurfactants, such as, for example, Control lauryl ether sulfate, betaines, amphoacetates and acyl glutamates. This showed that e.g. in the case of mixtures of lactosides of laureth-2 and 1185 laureth-3, the addition of 0.5 and 1% by weight of cosurfactant (sodium cocoamphoacetate, cocamidopropylbetaine, disodium cocoylglutamate, at 3% by weight total content) improves the foaming behavior.

A cosurfactant according to the invention is the maltose glycoside of ethylhexylglycerol.

1190 sugar derivatives of 1-O- (2-ethylhexyl) -glycerol are still unknown. Only the use of 1-O- (2-ethylhexyl) glycerol in personal care products is described in DE414047, DE4240674, EP599433 and US5516510. Especially preferred as cosurfactants are glycosides of 1-O- (2-ethylhexyl) -glycerol based on maltose. Both the glycoside at the primary and at the secondary hydroxy group

1195 of glycerol, as well as the mixture enhance the foaming of the compounds of the invention. The stability of the foams and the fine pores are also increased. Particularly advantageous proved a 1: 1 mixture of Lac-PG-C12 and the cosurfactant MaI-EHG described here. Furthermore, the use of the surfactants according to the invention as cosurfactants in

1200 mixtures with lauryl ether sulfate to improve the foam properties or allows to improve the skin compatibility compared to a formulation containing only lauryl ether sulfate.

Example 12

1205 Foam pattern and size distribution of the gas bubbles after 0 min. (Fig. 2 and 3) and after 10 min. (Figures 4 and 5) of Lac-EG-C12 in a total concentration of 1% by weight. in water. It can be seen that the foam at the beginning almost exclusively from bubbles with a pore size of less than 10,000 microns ² . After 10 min. The size distribution is somewhat flatter, with still around one quarter of the bubbles has a size of less than 1210 10000 microns ² .

Example 13

Foam pattern and size distribution of the gas bubbles after 0 min. (Fig. 6 and 7) and after 10 min. (Figures 8 and 9) of a mixture of Lac-PG-C12 / MaI-EHG in the ratio 1: 1 and 1215 of a total concentration of 1% by weight. in water. It can be seen in this example, which is also formed as in the previous example, at the beginning of a very fine-pored foam, in which after 10 min. also dominate the bubbles with a size of less than 10000 microns ² .

1220 Example 14

Foam pattern and size distribution of the gas bubbles after 0 min. (Figures 10 and 11) and after 10 min. (FIGS. 12 and 13) of a lauryl ether sulfate-containing surfactant mixture in a total concentration of 15% by weight. in water. In contrast to the two previous examples, you can see that already immediately formed foam a very

1225 wide size distribution of the gas bubbles, so it is coarse-pored. After 10 min. the size distribution has even shifted to sizes in excess of 100,000 μm ² .

1230

compatibility

Surprisingly, some of the compounds of the invention are characterized by a significantly better skin compatibility and a significantly lower irritation of the mucous membrane compared to lauryl ether sulfate, lauryl sulfate and even APG. The 1235 compatibility studies were carried out by methods known from the literature (Pape, W., Pfannenbecker, U., Hoppe, U .: Validation of the red blood cell test as an in vitro assay for the rapid screening of irritation potential of surfactants, Molecular Toxicology 1, 525 -536 1987)

1240 Example 15

Hemolysis test ,. H50 value after 10 min., For lauryl ether sulfate, APG (Plantaren 2000UP, Cognis) and Lac-EG-C12. See Figure 6.

1245 Example 16

Denaturation, D1 (in%), for lauryl ether sulfate, APG (Plantaren 2000UP, Cognis) and

Lac-EC-12th

See Figure 7.

1250

Example 17

Quotient L / D from H50 and Dl, for lauryl ether sulfate, APG and Lac-EG-C12.

1255 See Figure 8.

Examples of surfactant mixtures

1260 Preparation of the mixture in Example 18:

The surfactant is suspended in water and heated until a clear solution is obtained, but not above 60 ^° C. Subsequently, the 50 ° C. warm solution is adjusted to a pH of 5.5 with citric acid. Upon cooling, a gel is formed.

1265 Example 18

Gesichtsreinigungsgel

Preparation of the mixture in Example 19:

1270 To a solution of lauryl ether sulfate in water sugar surfactant according to the invention is added and the mixture heated to the setting of a clear solution, but does not exceed 60 ⁰ C. Subsequently, the 50 ⁰ C warm solution is adjusted with citric acid to pH 5.5.

1275 Example 19

shower preparation

Preparation of the mixtures in Examples 20 and 21:

To a solution of lauryl ether sulfate in water, the inventive

1280 sugar surfactant is added and the mixture is heated until a clear solution is obtained, but not above 60 ^° C. The citric acid is then adjusted to a pH of 5.5 by adding the solution at 50 ° C. A gel forms on cooling

1285

Preparation of the mixtures in Example 22-30:

1290 To a solution of the cosurfactant in water sugar surfactant according to the invention is added and the mixture heated to the setting of a clear solution, but does not exceed 60 ⁰ C. Subsequently, the 50 ⁰ C warm solution is adjusted with citric acid to pH 5.5. Upon cooling, a gel forms.

1295 Example 22

Make-up remover

Example 23 Handwashing Preparation

1300 Example 24

Dental care preparation

Example 25

1305 Example 26

1310 Example 27

1315

1320 Preparation of the mixture in Example 31:

1325 The surfactant mixture according to the invention is dissolved in water at room temperature and adjusted to pH 5.5 with citric acid.

Example 31 Cloth impregnation medium

1330

Preparation of the mixtures in Example 32-34:

The surfactant mixture according to the invention is dissolved at room temperature in a solution of lauryl ether sulfate and adjusted to pH 5.5 with citric acid.

1335 Example 32 Machine dishwashing detergent

1340 Example 34

1345 window cleaner

Preparation of the mixtures in Example 35-43:

The surfactant mixture according to the invention is dissolved at room temperature in a solution of

Dissolved 1350 cosurfactants and adjusted to pH 5.5 with citric acid.

Example 35

1355

Example 38

1360 Example 39

Example 40

Example 41

1365

Example 42

Example 43

Preparation of the mixtures in Example 44 and 45:

1370 To a solution of the cosurfactant MaI-EHG according to the invention, the surfactant Lac-PG-C12 according to the invention is added and heated until a clear solution is established, but not above 60 ° C. The 50 ⁰ C warm solution is adjusted to pH 5.5 with citric acid. Upon cooling, a gel forms.

1375 Example 44

Preparation of the mixture in Example 46:

1380 The surfactants of the invention are suspended in water and heated to a clear solution, but not above 60 ° C. The solution is adjusted to pH 5.5 with citric acid. 1385 Example 46

Preparation of the mixture in Example 47:

The surfactant of the invention is dissolved in water at room temperature and adjusted to pH 5.5 with 1390 citric acid.

Example 47

1395 Preparation of the mixtures in Example 48-50:

The surfactant of the invention is dissolved in a solution of the cosurfactant in water and adjusted to pH 5.5 with citric acid.

Example 48

1400 Example 49

1405

1410

Claims

claims:

1. Compounds according to the formula

1415 A- (B) _x -C

in which

A is a reducing di- or trisaccharide,

B is a polyhydric alcohol having 2 to 4 carbon atoms or its derivative, 1420 C is a branched or unbranched, saturated or unsaturated

Fatty alcohol radical having 8 to 22, particularly preferably 8 to 14 or 14 to 22, very particularly preferably up to 20 C atoms,

A glycosidically linked to B in position 1,

B is etherified with C and 1425 x has the value 1 to 50.

2. Compounds according to claim 1, characterized in that the reducing di- or trisaccharide A is selected from the group of maltose, lactose, melibiose, cellobiose.

1430

3. Compounds according to one of the preceding claims, characterized in that and B is selected from the group of ethylene glycol, diethylene glycol, triethylene glycol, tetraethylene glycol, propane-1, 2-diol, propane-1, 3-diol, dipropylene glycol, glycehne, butanediol, pentaerythritol.

1435

4. Compounds according to one of the preceding claims, characterized in that C is a linear fatty alcohol radical.

5. Compounds according to one of the preceding claims characterized 1440 characterized in that C is a saturated fatty alcohol residue.

6. Compounds according to one of the preceding claims, characterized in that are used for the application as a surfactant fatty alcohols having C8 to C14 atoms

1445 7. Compounds according to one of the preceding claims, characterized in that are used for use as an emulsifier fatty alcohols having C12 to C22 atoms

8. surfactant or emulsifier system

1450 - alkyl ether sulfate, for example sodium, ammonium, magnesium,

MIPA, TIPA laureth sulfate, sodium myrethsulfate and sodium C _12-I3 pareth sulfate,

Alkyl sulfates, for example sodium, ammonium and TEA lauryl sulfate,

Sodium alkyl sulfates such as sodium cetearyl sulfate

1455 and at least one compound according to any one of the preceding

Claims.

9. Cosmetic preparation containing a compound according to one of the claims 1 to 7 or containing a surfactant system according to claim

1460 8.

10. Cleaning agent for household or for technical purposes comprising a compound according to one of the claims 1 to 7 or containing a surfactant system or emulsifier system according to claim 8.

1465

11. Food preparation containing a compound according to one of the claims 1 to 7 or containing a surfactant system or emulsifier system according to claim 8.

12. A foamable or foamable preparation containing a compound according to one of the claims 1 to 7 or containing a surfactant system according to claim 8.

13. Use of a compound according to any one of claims 1 to 7 or 1475 of a surfactant system according to claim 8 for the manufacture of a medicament.

14. Use of a compound according to any one of claims 1 to 7 for improving the foamability of a water-containing preparation.

15. Use of product 14 according to Example 7a, ((2'-dodecyloxyethyl) 4-O- (β-D-1480 galactopyranosyl) -β-D-glucopyranoside) and / or ((2'-dodecyloxypropyl) 4-O-LSS

D-galactopyranosyl) -β-D-glucopyranoside) as a gelling agent and / or as a foaming agent for aqueous systems.

16. A process for preparing a compound according to any one of the preceding 1485 claims by reacting a ß-peracetate of component A with a Lewis acid and the polyol A _x -B.

17. Process for the preparation of a compound according to one of the preceding claims by trans glycosylation from butyl glycosides, propyl glycosides,

1490 Ethyl glycosides, methyl glycosides with polyol ethers A _x -B.