Surfactant composition comprising ether compound and catalytic process for manufacturing thereof

• US 9,884,799 B2
• Filed: 10/07/2014
• Issued: 02/06/2018
• Est. Priority Date: 10/11/2013
• Status: Expired due to Fees

• Current Assignee: Centre National De La Recherche Scientifique, Rhodia Operations (Solvac SA)
• Original Assignee: Centre National De La Recherche Scientifique, Rhodia Operations (Solvac SA)
• Inventors: Feng, Xiaoshuang, Decampo, Floryan, Zhao, Yan, Fan, Zhaoyu, Merlo, Luca, Oldani, Claudio
• Primary Examiner(s): Witherspoon, Sikarl
• Application Number:
  US15/027,645
• Publication Number:
  US 20160251290A1
• Time in Patent Office: 1,218 Days
• CPC Class Codes: B01J 31/10 sulfonated
• CPC Class Codes: C07C 41/09 by dehydration of compounds containing hydroxy groups
• CPC Class Codes: C07C 43/13 containing hydroxy or O-metal groups C07C43/11 takes precedence
• CPC Class Codes: C08G 2650/54 Polyglycerols
• CPC Class Codes: C08G 65/34 from hydroxy compounds or their metallic derivatives C08G65/26 takes precedence
• CPC Class Codes: C08L 71/00 Compositions of polyethers obtained by reactions forming an ether link in the main chain of polyacetals C08L59/00; of epoxy resins C08L63/00; of polythioether-ethers C08L81/02; of polyether-sulfones C08L81/06; Compositions of derivatives of such polymers
• CPC Class Codes: C11D 1/72 Ethers of polyoxyalkylene glycols

Abstract

Disclosed is a process for preparing at least one ether compound, comprising reacting at least one alcohol (I) with at least one polyol (II) in the presence of a functional polymer [polymer (F)] as a catalyst (X), wherein: the alcohol (I) is represented by the general formula (1): R1-OH (1) wherein R1 is a hydrocarbon group having 1 to 36 carbon atoms, the polyol (II) is represented by the general formula (2): R2-(OH) m (2) wherein R2 represents the skeleton moiety of the polyol and m is an integer of from 2 to 20, and polymer (F) is a polymer comprising recurring units derived from at least one ethylenically unsaturated monomer [monomer (M)] and bearing at least one cation exchange group. Further disclosed is a surfactant composition obtained by said process, and featuring an excellent detergency performance.

Claims

1. A process for preparing at least one ether compound, the process comprising reacting at least one alcohol (I) with at least one polyol (II) in the presence of a functional polymer [polymer (F)] as a catalyst (X), wherein:

the alcohol (I) is a compound represented by the general formula (1);

R₁—

OH 

 

(1)

wherein R₁ is a hydrocarbon group having 1 to 36 carbon atoms, the polyol (II) is represented by the general formula (2);

R₂—

(OH)_m 

 

(2)

wherein R₂ represents the skeleton moiety of the polyol and m is an integer of from 2 to 20,

and the polymer (F) is a polymer comprising recurring units derived from at least one ethylenically unsaturated monomer [monomer (M)] and bearing at least one cation exchange group;

wherein the reaction of the at least one alcohol (I) with the at least one polyol (II) in the presence of the functional polymer [polymer (F)] as the catalyst is performed in the absence of a solvent, and a medium for the reaction of the at least one alcohol (I) with the at least one polyol (II) in the presence of the functional polymer [polymer (F)] as the catalyst is substantially free of any surfactant at the start of the reaction.

2. The process of claim 1, wherein the at least one cation exchange group in the polymer (F) is selected from the group consisting of:

SO₂X, wherein X is halogen or —

O⁻

M⁺, wherein M⁺ is a cation selected from the group consisting of H⁺, NH₄⁺, K⁺, Li⁺, Na⁺, and mixtures thereof;

COY, wherein Y is halogen;

—

O⁻

M⁺, wherein M⁺ is a cation selected from the group consisting of H⁺, NH₄⁺, K⁺, Li⁺, and Na⁺;

—

OR_Hy wherein R_Hy is a C₁-C₆ hydrocarbon group;

—

OR_Hf wherein R_Hf is a C₁-C₆ fluorocarbon or per(halo)fluorocarbon group;

—

N(R_Hy*)₂, wherein R_Hy*, equal or different at each occurrence, is hydrogen or a C₁-C₆ hydrocarbon group, or mixtures thereof; and

PO₂Z, wherein Z is halogen;

—

O⁻

M⁺, wherein M⁺ is a cation selected from the group consisting of H⁺, NH₄⁺, K⁺, Li⁺, and Na⁺;

—

OR_Hy wherein R_Hy is a C₁-C₆ hydrocarbon group, —

OR_Hf′

wherein R_Hf is a C₁-C₆ fluorocarbon or per(halo)fluorocarbon group, or mixture thereof.

3. The process of claim 2, wherein each of X, Y and Z is independently —

O⁻

H⁺.

4. The process of claim 2, wherein the cation exchange group complies with formula —

SO₂X.

5. The process of claim 2, wherein the polymer (F) comprises recurring units derived from styrene.

6. The process of claim 4, wherein the polymer (F) is selected from a group consisting of sulfonated styrene-divinylbenzene copolymers, sulfonated crosslinked styrene polymers, phenol-formaldehyde-sulfonic acid copolymers, and benzene-formaldehyde-sulfonic acid copolymers.

7. The process of claim 1, wherein the polymer (F) consists essentially of:

recurring units derived from one or more than one ethylenically unsaturated monomer comprising at least one fluorine atom and free from hydrogen atoms; and

recurring units derived from one or more than one ethylenically unsaturated monomer comprising at least one fluorine atom and at least one cation exchange group, and free from hydrogen atoms (except those optionally in the cation exchange group).

8. The process of claim 7, wherein the polymer (F) consists essentially of:

from 5 to 25% by moles of recurring units derived from (perfluoro-2-(2-fluorosulfonylethoxy)propylvinyl ether) (PSEPVE) and/or perfluoro-5-sulphonylfluoride-3-oxa-1-pentene (SFVE), in their —

SO₂F or —

SO₂X″

form, wherein X″

is halogen or —

O⁻

M⁺, wherein M⁺ is a cation selected from the group consisting of H⁺, NH₄⁺, K⁺, Li⁺, Na⁺, or mixtures thereof; and

from 95 to 75% by moles of recurring units derived from tetrafluoroethylene (TFE).

9. The process of claim 1, wherein the polymer (F) is used as a supported catalyst (X).

10. The process of claim 1, wherein the polymer (F) is grafted to or supported on solid particles having a medium diameter between 2 and 200 nm.

11. The process of claim 9, wherein the polymer (F) comprises recurring units derived from styrene.

13. The process of claim 1, wherein the process comprises the following steps:

a) mixing the at least one alcohol (I), the at least one polyol (II), and the catalyst (X);

b) proceeding to the reaction of the ether compound by setting a temperature (T); and

c) isolating the ether compound,

wherein the ether compound includes at least one MAGE compound of formula (4)

14. The process of claim 2, wherein the halogen is Cl, F, Br, or I.

15. The process of claim 8, wherein M⁺ is H⁺.

16. The process of claim 10, wherein the solid particles having a medium diameter between 10 and 50 nm.

12. A surfactant composition [composition (S)] consisting of:

(i) more than one ether compound of formula (3) [ether (E1)],

17. An application for home care or personal care comprising the composition (S) of claim 12.