# US 2010/0168252 A1 · Sugar derivatives, method for preparation thereof, their use as surface-active agents

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- Number: US 2010/0168252 A1
- Document ID: US20100168252A1
- Status: Published application
- Kind: A1
- Application number: 12/307,629
- Filed: 2007-07-05
- Published: 2010-07-01
- Earliest claimed: 2006-07-10
- Inventors: Jerome Guilbot; Herve Rollan; Daniel Muller
- Web page: https://patentgrep.com/patent/US20100168252A1

## CPC

- C11D 3/2013: {fatty or with at least 8 carbon atoms in the alkyl chain}
- A61K 8/602: {Glycosides, e.g. rutin}
- A61Q 19/00: Preparations for care of the skin
- C07C 41/01: Preparation of ethers
- C07C 43/13: containing hydroxy or O-metal groups (C07C43/11 takes precedence)
- C07C 43/135: {having more than one ether bond}
- C07H 15/08: Polyoxyalkylene derivatives
- C11D 1/662: {Carbohydrates or derivatives}
- C11D 3/2017: {branched}
- C11D 3/202: {fatty or with at least 8 carbon atoms in the alkyl chain}
- C11D 3/2031: {fatty or with at least 8 carbon atoms in the alkenyl chain}
- C11D: DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- A61K: PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES (devices or methods specially adapted for bringing pharmaceutical products into particular physical or administering forms A61J3/00; chemical aspects of, or use of materials for deodorisation of air, for disinfection or sterilisation, or for bandages, dressings, absorbent pads or surgical articles A61L; soap compositions C11D)
- A61Q: SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- C07C: ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07H: SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS (derivatives of aldonic or saccharic acids C07C, C07D; aldonic acids, saccharic acids C07C59/105, C07C59/285; cyanohydrins C07C255/16; glycals C07D; compounds of unknown constitution C07G; polysaccharides, derivatives thereof C08B; DNA or RNA concerning genetic engineering, vectors, e.g. plasmids, or their isolation, preparation or purification C12N15/00; sugar industry C13)

## Abstract

Composition (C) comprising for 100% of its mass: from 0.5% to 30% of one or more alcohols having the formula (IV): R1-OH (IV) wherein R1 represents a saturated or unsaturated, linear or branched aliphatic group, having from 8 to 36 carbon atoms, optionally substituted with one or more hydroxyl and/or groups and by 70% to 99.5% of one or more compounds having the formula (I): wherein R represents a linear or branched aliphatic group having from one to eight carbon atoms optionally substituted by one or more hydroxy groups, n represents a whole number greater than or equal to 1 and less than or equal to 10, R1 is such as defined previously for formula (IV), at least one of the groups Z1 or Z2 represents a group (II) wherein —S— represents the divalent remainder of a reducing sugar and p represents a decimal number greater than or equal to 1 and less than or equal to 10 and the other group Z1 or Z2 represents a hydrogen atom or said group (III). Method for preparation thereof and use of composition (C) as surfactant.

## Claims

### Claim at position 1

1-14. (canceled)

### Claim 15

A composition (C) comprising per 100% of its mass:
from 0.5% to 30% of one or more alcohols of the formula (IV):
R1-OH (IV)
in which R1 represents a saturated or unsaturated, linear or branched aliphatic radical having from 8 to 36 carbon atoms, optionally substituted with one or more hydroxyl groups, and
from 70% to 99.5% of one or more compounds of formula (I):
in which R represents a linear or branched alkyl radical having from one to eight carbon atoms optionally substituted with one or more hydroxyl radicals, n represents an integer greater than or equal to 1 and less than or equal to 10, R1 is as defined previously for formula (IV), at least one of the radicals Z1 or Z2 represents a radical:
in which —S— represents the divalent residue of a reducing sugar and p represents a decimal number greater than or equal to 1 and less than or equal to 10 and the other one of the radicals Z1 or Z2 represents a hydrogen atom or said radical:

### Claim 16 (depends on 15)

The composition (C) of claim 15, wherein in formulas (I) and (IV) R1 represents a radical selected from the radicals octyl, decyl, dodecyl, tetradecyl, hexadecyl, octadecyl, eicosyl, 2-ethylhexyl, 2-butyloctyl, 2-butyldecyl, 2-hexyloctyl, 2-hexyldecyl, 2-hexyldodecyl, 2-octyldecyl, 2-octyldodecyl, 2-decyltetradecyl, isododecyl, isotetradecyl, isohexadecyl, isooctadecyl, 10-undecenyl, oleyl, isooleyl, linoleyl, linolenyl or 10,13-eicosadienyl, 12-hydroxystearyl and 2-propylheptyl.

### Claim 17 (depends on 15)

The composition (C) of claim 15, wherein in formula (I), —S— represents a divalent glucose residue.

### Claim 18 (depends on 15)

The composition (C) of claim 15, wherein in formula (I), S represents a divalent xylose residue.

### Claim 19 (depends on 15)

The composition (C) of claim 15, wherein in formula (I), p is between 1.005 and 5.

### Claim 20 (depends on 16)

The composition (C) of claim 16, wherein in formula (I), p is between 1.05 and 2.

### Claim 21 (depends on 15)

The composition (C) of claim 15, wherein in formula (I), R is selected from the methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl and hydroxymethyl radicals.

### Claim 22 (depends on 16)

The composition (C) of claim 16, for which in formula (I), —S— represents a divalent glucose residue.

### Claim 23 (depends on 16)

The composition (C) of claim 16, for which in formula (I), S represents a divalent xylose residue.

### Claim 24 (depends on 16)

The composition (C) of claim 16, for which in formula (I), p is between 1.005 and 5.

### Claim 25 (depends on 22)

The composition (C) of claim 22, for which in formula (I), p is between 1.005 and 5.

### Claim 26 (depends on 23)

The composition (C) of claim 23, for which in formula (I), p is between 1.005 and 5.

### Claim 27 (depends on 16)

The composition (C) of claim 16, for which in formula (I), R is selected from the methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl and hydroxymethyl radicals.

### Claim 28 (depends on 22)

The composition (C) of claim 22, for which in formula (I), R is selected from the methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl and hydroxymethyl radicals.

### Claim 29 (depends on 23)

The composition (C) of claim 23, for which in formula (I), R is selected from the methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl and hydroxymethyl radicals.

### Claim 30

A method of preparing a composition (C) comprising per 100% of its mass:
from 0.5% to 30% of one or more alcohols of the formula (IV):
R1-OH (IV)
in which R1 represents a saturated or unsaturated, linear or branched aliphatic radical having from 8 to 36 carbon atoms, optionally substituted with one or more hydroxyl groups, and
from 70% to 99.5% of one or more compounds of formula (I):
in which R represents a linear or branched alkyl radical having from one to eight carbon atoms optionally substituted with one or more hydroxyl radicals, n represents an integer greater than or equal to 1 and less than or equal to 10, R1 is as defined previously for formula (IV), at least one of the radicals Z1 or Z2 represents a radical:
in which —S— represents the divalent residue of a reducing sugar and p represents a decimal number greater than or equal to 1 and less than or equal to 10 and the other one of the radicals Z1 or Z2 represents a hydrogen atom or said radical:
comprising the following successive stages of chemical reactions:
a) the reaction of an alcohol of formula (IV):
R1-OH (IV)
in which R1 represents a saturated or unsaturated, linear or branched aliphatic radical having from 8 to 36 carbon atoms, optionally substituted with one or more hydroxyl groups or of a mixture of alcohols of formula (IV), with a 3,3-disubstituted oxetane of formula (V):
in which R represents a linear or branched alkyl radical having from one to eight carbon atoms optionally substituted with one or more hydroxyl radicals, leading to a mixture (M) comprising the alcohol of formula (IV) that had not reacted and one or more compounds of formulas (II):
in which R and R1 are as defined previously and n represents an integer greater than or equal to 1 and less than or equal to 10; and
b) the reaction of said mixture (M) with a reducing sugar of formula (III):
S—H (III)
to obtain said composition (C).

### Claim 31 (depends on 30)

The method of claim 30, wherein said method additionally comprises an additional step c) the dehydration of a compound of formula (VII):
in which R is as defined previously, to obtain the compound of formula (V).

### Claim 32 (depends on 15)

A compound of formula (Ia):
wherein R1 represents a saturated or unsaturated, linear or branched aliphatic radical having from 8 to 36 carbon atoms, optionally substituted with one or more hydroxyl groups, R represents a linear or branched alkyl radical having from one to eight carbon atoms optionally substituted with one or more hydroxyl radicals, n represents an integer greater than or equal to 1 and less than or equal to 10, —S— represents the divalent residue of a reducing sugar and p represents a decimal number greater than or equal to 1 and less than or equal to 10, said compound of formula (Ia) corresponding to formula (I) of claim 15, in which one of the radicals Z1 or Z2 represents a hydrogen atom and the other one the radical:

### Claim 33 (depends on 32)

The compound of claim 32, wherein the compound is of the formula (Ia1):
said compound corresponding to formula (Ia) of claim 32 in which n is equal to 1.

### Claim 34 (depends on 33)

The compound of claim 33, said compound having the formula (Ia3):
Said compound corresponding to formula (Ia1) of claim 33, in which R represents an ethyl radical.

### Claim 35 (depends on 33)

The compound of claim 33, said compound having the formula (Ia4):
Said compound corresponding to formula (Ia1) of claim 33, in which R represents a hydroxymethyl radical.

### Claim 36 (depends on 15)

A compound of formula (Ic):
wherein R1 represents a saturated or unsaturated, linear or branched aliphatic radical having from 8 to 36 carbon atoms, optionally substituted with one or more hydroxyl groups, R represents a linear or branched alkyl radical having from one to eight carbon atoms optionally substituted with one or more hydroxyl radicals, n represents an integer greater than or equal to 1 and less than or equal to 10, each —S— represents the divalent residue of a reducing sugar and each p represents a decimal number greater than or equal to 1 and less than or equal to 10, said compound of formula (Ic) corresponding to formula (I) of claim 15, in which each of the radicals Z1 or Z2 represents the radical:

### Claim 37 (depends on 15)

The composition (C) of claim 15, wherein said composition is a surfactant.

### Claim 38 (depends on 15)

The composition (C) of claim 15, wherein said composition is a foaming agent, an emulsifier, a wetting agent, a dispersant or a detergent.

### Claim 39 (depends on 32)

The compound of claim 32, wherein said compound is a surfactant.

### Claim 40 (depends on 32)

The compound of claim 32, wherein said compound is a foaming agent, an emulsifier, a wetting agent, a dispersant or a detergent.

### Claim 41 (depends on 36)

The compound of claim 36, wherein said compound is a surfactant.

### Claim 42 (depends on 36)

The compound of claim 36, wherein said compound is a foaming agent, an emulsifier, a wetting agent, a dispersant or a detergent.

### Claim 43

A cosmetic or pharmaceutical composition, wherein said cosmetic or pharmaceutical composition contains as a surfactant a composition (C) comprising per 100% of its mass:
from 0.5% to 30% of one or more alcohols of the formula (IV):
R1-OH (IV)
in which R1 represents a saturated or unsaturated, linear or branched aliphatic radical having from 8 to 36 carbon atoms, optionally substituted with one or more hydroxyl groups, and
from 70% to 99.5% of one or more compounds of formula (I):
in which R represents a linear or branched alkyl radical having from one to eight carbon atoms optionally substituted with one or more hydroxyl radicals, n represents an integer greater than or equal to 1 and less than or equal to 10, R1 is as defined previously for formula (IV), at least one of the radicals Z1 or Z2 represents a radical:
in which —S— represents the divalent residue of a reducing sugar and p represents a decimal number greater than or equal to 1 and less than or equal to 10 and the other one of the radicals Z1 or Z2 represents a hydrogen atom or said radical:

### Claim 44 (depends on 15)

A cosmetic or pharmaceutical composition, wherein said cosmetic or pharmaceutical composition contains as a surfactant at least one compound of the formula (Ia):
corresponding to formula (I) of claim 15, in which one of the radicals Z1 or Z2 represents a hydrogen atom and the other one the radical: