# US 4,398,912 A · Cyclical tensio-active polyethers

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- Number: US 4,398,912 A
- Document ID: US4398912A
- Status: Granted
- Kind: A
- Application number: 06/288,361
- Filed: 1981-07-30
- Granted: 1983-08-16
- Earliest claimed: 1978-03-17
- Assignees: L'oreal
- Inventors: Guy Vanlerberghe; Henry Sebag
- Web page: https://patentgrep.com/patent/US4398912A

## CPC

- C07D 323/00: Heterocyclic compounds containing more than two oxygen atoms as the only ring hetero atoms
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)

## Abstract

Cyclical polyethers having amphiphile groups are derived from the tetramer of epichlorhydrin. These are useful in the solubiliization of various products.

## Claims

### Claim 1

Cyclical tensio-active polyethers of the general formula: ##STR80## in which A is an amphiphile grouping selected from the group consisting of:
(e) the grouping: ##STR81## where R.sub.4 refers to an alkyl radical having from 6 to 20 carbon atoms, u refers to 0 or 1, w refers to 0 or 1, and Z refers to a grouping of atoms with hydrophile characteristics selected from the group consisting of: ##STR82## where x represents 1 or 2, y represents 2 or 3, and n represents a number from 1 to 20;
(e.sub.1) the grouping: ##STR83## where each of j and k refer to a whole number or a fraction lower than 20, the sum j+k being between 1 and 20, u refers to 0 or 1, and R.sub.4 refers to an alkyl radical having from 6 to 20 carbon atoms;
(f) the grouping: ##STR84## where L refers to a hydrogen atom and one of the groupings:
--CH.sub.2 --CHOH--CH.sub.2 --(O).sub.q --R.sub.5
where q refers to 0 or 1, ##STR85## the hydrogen atom and the other grouping being distributed is statistical fashion, R.sub.5 refers to a linear alkyl radical having from 6 to 18 carbon atoms, p refers to a whole number or a fraction from 1 to 10 and represents an average statistical value, and Y refers to: ##STR86## (g) the grouping: ##STR87## where v refers to a whole number or a fraction from 0 to 20, R.sub.6 refers to a hydrogen atom or the radical --SO.sub.3 H, and R.sub.5 has the meaning indicated above;
(h) the grouping (e) or (e.sub.1) wherein the thioether or sulphoxide grouping, or the tertiary amine grouping for (e) is alkylated by an alkylation agent selected from the group consisting of methyl bromide, methyl iodide and dimethyl sulphate; and
(i) the grouping (f) wherein the thioether or sulphoxide grouping of (f) is alkylated by an alkylation agent selected from the group consisting of methyl bromide, methyl iodide and dimethyl sulphate.

### Claim 2 (depends on 42)

The polyethers of claim 42, wherein the amphiphile grouping A is the grouping (i).

### Claim 3 (depends on 1)

The polyethers of claim 1, wherein A is selected from the group consisting of:
(e) the grouping: ##STR88## where R.sub.4 refers to an alkyl radical having from 6 to 20 carbon atoms, u refers to 0 or 1, w refers to 0 or 1, and
Z refers to a grouping of atoms with hydrophile characteristics selected from the group consisting of: ##STR89## where x represents 1 or 2, y represents 2 or 3, and n represents a number from 1 to 20;
(f) the grouping: ##STR90## where L refers to a hydrogen atom and one of the groupings: ##STR91## the hydrogen atom and the other grouping being distributed in statistical fashion, R.sub.5 refers to a linear alkyl radical having from 6 to 18 carbon atoms, p refers to a whole number or a fraction from 1 to 10 and represents an average statistical value, and Y refers to: ##STR92## (g) the grouping: ##STR93## where v refers to a whole number or a fraction from 0 to 20, R.sub.6 refers to a hydrogen atom or the radical --SO.sub.3 H, and R.sub.5 has the meaning indicated above; and
(i) the grouping (f) alkylated by an alkylation agent selected from the group consisting of methyl bromide, methyl iodide and dimethyl sulphate.

### Claim 4 (depends on 1)

The polyethers of claim 1, wherein A is the grouping (f).

### Claim 5 (depends on 1)

The polyethers of claim 1, wherein A is the grouping (g).

### Claim 6 (depends on 1)

The polyethers of claim 1, wherein A is ##STR94## wherein L is hydrogen and the grouping ##STR95## distributed in statistical fashion in the proportions 3/1.

### Claim 7 (depends on 1)

The polyether of claim 1, wherein A is ##STR96## wherein L is hydrogen and the grouping --CH.sub.2 --CHOH--C.sub.10 H.sub.21 distributed in statistical fashion in the proportions 6/1.

### Claim 8 (depends on 1)

The polyethers of claim 1, wherein A is ##STR97## wherein R.sub.5 is C.sub.14 H.sub.29.

### Claim 9 (depends on 1)

The polyethers of claim 1, wherein A is ##STR98##

### Claim 10 (depends on 1)

The polyethers of claim 1, wherein A is ##STR99## where L is a hydrogen atom and one of the groupings: ##STR100## the hydrogen atom and the other grouping being distributed in statistical fashion, and R.sub.5 refers to an alkyl linear radical having from 6 to 18 carbon atoms.

### Claim 11 (depends on 1)

The polyethers of claim 1, wherein A is ##STR101## wherein R.sub.5 is a linear alkyl radical having from 6 to 18 carbon atoms.

### Claim 12 (depends on 1)

The polyethers of claim 1, wherein A is the group (e.sub.1).

### Claim 13 (depends on 1)

The polyethers of claim 1, wherein A is the group (h).

### Claim 14 (depends on 1)

Composition for shampooing hair comprising at least 0.5.times.10.sup.-3 weight percent based on the total weight of the composition of a polyether of claim 1 in solution in a solvent selected from the group consisting of water and water-alcohol, wherein said alcohol is an alcohol having from 1 to 4 carbon atoms, said alcohol comprising 5 to 70% of the total weight of the composition.

### Claim 15 (depends on 14)

The composition of claim 14 wherein said alcohol is selected from the group consisting of ethanol and isopropanol.

### Claim 16 (depends on 14)

The composition of claim 14 further containing adjuvants usually employed in compositions for shampoos.

### Claim 17 (depends on 16)

The composition of claim 16 wherein said adjuvants are selected from the group consisting of anionic, cationic, amphoteric, zwitterionic or ion-ionic surface active agents, perfumes, preservatives, foam synergists, foaming agents, foaming stabilizers and cosmetic resins.

### Claim 18 (depends on 1)

Composition for dyeing hair comprising at least 0.5.times.10.sup.-3 weight percent based on the total weight of the composition of a polyether of claim 1 in solution in a solvent selected from the group consisting of water and water-alcohol, wherein said alcohol is an alcohol having from 1 to 4 carbon atoms, said alcohol comprising 5 to 70% of the total weight of the composition, as well as 0.001 to 1% by weight of the total weight of the composition of one or several dyes selected from the group consisting of anthraquinone dyes, azoic dyes, nitrobenzene dyes, indoanilines, indophenols and indamines.

### Claim 19 (depends on 18)

The composition of claim 18 wherein said alcohol is selected from the group consisting of ethanol and isopropanol.

### Claim 20 (depends on 18)

The composition of claim 18 further containing adjuvants usually employed in compositions for dyeing hair.

### Claim 21 (depends on 20)

The composition of claim 20 wherein said adjuvants are selected from the group consisting of anionic, cationic, non-ionic, or amphoteric surface active agents, perfumes, preservatives, thickeners, softeners, sequestering agents, swelling agents and cosmetic resins.

### Claim 22 (depends on 1)

A procedure for shampooing hair comprising the application, on human hair, of an effective quantity of a composition, having in solution in a solvent selected from the group consisting of water and water-alcohol, wherein said alcohol is an alcohol having from 1 to 4 carbon atoms, said alcohol comprising 5 to 70% of the total weight of the composition, at least 0.5.times.10.sup.-3 weight percent based on the total weight of the composition of a polyether of claim 1.

### Claim 23 (depends on 1)

A procedure for dyeing hair comprising the application on human hair of an effective quantity of a composition having, in solution in a solvent selected from the group consisting of water and water-alcohol, wherein said alcohol is an alcohol having from 1 to 4 carbon atoms, said alcohol comprising 5 to 70% of the total weight of the composition, of at least 0.5.times.10.sup.-3 weight percent based on the total weight of the composition of a polyether of claim 1, as well as 0.001 to 1% by weight of the total weight of the composition of one or several dyes selected from the group consisting of anthraquinone dyes, azoic dyes, nitrobenzene dyes, indoanilines, indophenols and indamines.