Polymeric surfactant

Patent metadata

Field	Value
Publication number	US-2016145382-A1
Application number	US-201414651246-A
Country	US
Kind code	A1
Filing date	Jul 1, 2014
Priority date	Jul 22, 2013
Publication date	May 26, 2016
Grant date	—

Abstract

Surfactant compositions including sulfonated polyester polyethers, and methods of making such compositions, are described. A diol is reacted with an anhydride having residual unsaturation, and the resulting polymer is sulfonated under mild acid-base conditions. Sulfonation occurs at the residual unsaturation. If maleic anhydride is used, sulfonation occurs at locations alpha to carbonyl carbons in the polymer.

First claim

1 . A sulfonated polyether polyester surfactant.

2 . The sulfonated polyether polyester surfactant of claim 1 , wherein each of the sulfonate groups is alpha to an ester group.

3 . The sulfonated polyether polyester surfactant of claim 1 , wherein a ratio of ether linkages to ester linkages is between about 25:1 and about 1:1.

4 . The sulfonated polyether polyester surfactant of claim 2 , wherein the sulfonated polyether polyester surfactant is an anion.

5 . The sulfonated polyether polyester surfactant of claim 4 , wherein a ratio of molecular weight to valence of the surfactant anion is between 1,000 and 10,000.

6 . The sulfonated polyether polyester surfactant of claim 5 , further comprising an alkali metal or alkaline earth metal ion.

7 . The sulfonated polyether polyester surfactant of claim 3 , wherein each ether linkage links two hydrocarbyl chains having between 6 and 24 carbon atoms.

8 . The sulfonated polyether polyester surfactant of claim 7 , wherein each ester linkage is between a sulfonated hydrocarbyl chain and a polyether chain.

9 . A composition comprising a surfactant having the formula
HO(R 1 O) q (R 2 O) r [COXR 3 COO(R 1 O) q (R 2 O) r]s [COR 6 COO(R 4 O) t (R 5 O) u O] w HM v (s+w)/v
Wherein R 1 , R 2 , R 3 , R 4 , R 5 , and R 6 are all, independently, alkylene groups, each occurrence of X is an alkylsulfonate group having the formula C a H 2a-b (SO 3 − ) b , where a and b are integers from 1 to 10, q is an integer from 0 to 20, r is an integer from 0 to 20, s is an integer from 1 to 500, t is an integer from 0 to 20, u is an integer from 0 to 20, w is an integer from 1 to 500, and M is a cation of valence v.

10 . The composition of claim 9 , further comprising water and a solvent.

11 . The composition of claim 10 , wherein R 1 , R 2 , R 4 and R 5 are each, independently, a C 2 to C 24 alkylene group.

12 . The composition of claim 11 , wherein R 1 and R 4 are each, independently, CH 2 , and r and u are 0.

13 . The composition of claim 12 , wherein the surfactant has a molecular weight between about 300 and about 50,000.

14 . The composition of claim 13 , wherein the surfactant has a ratio of weight-average molecular weight to number-average molecular weight between about 2.1 and about 10.0.

15 . The composition of claim 14 , wherein every SO 3 − group is alpha to a carbonyl oxygen atom.

16 . The composition of claim 15 , wherein R 1 , R 2 , R 4 , and R 5 are each selected from the group consisting of ethylene, propylene, butylene, pentylene, and hexylene.

17 . A method of making a a surfactant, comprising:
reacting an ester source having unsaturated carbon and an ether source to form a polyester polyether copolymer having unsaturated carbon; and sulfonating the unsaturated carbon.

18 . The method of claim 17 , wherein the ester source is an anhydride and the ether source is a diol.

19 . The method of claim 18 , wherein reacting the ester source having unsaturated carbon and the ether source comprises mixing the ester source having unsaturated carbon and the ether source in a solvent and adding a polymerization catalyst.

20 . The method of claim 18 , wherein sulfonating the unsaturated carbon comprises forming a reaction mixture of the polyester polyether copolymer having unsaturated carbon and a sulfonating agent and adding a buffer.

Assignees

• Huntsman Petrochemical Llc

Inventors

• Su Wei-Yang
• Champion Donald H

Classifications

• C08G63/916 Primary

  Dicarboxylic acids and dihydroxy compounds · CPC title

• C08L67/025

  containing polyether sequences · CPC title

• C08G63/6886

  Dicarboxylic acids and dihydroxy compounds · CPC title

• C08G63/672 Primary

  Dicarboxylic acids and dihydroxy compounds · CPC title

• C09K23/018

  Mixtures of two or more different organic oxygen-containing compounds · CPC title