# US 2010/0168318 A1 · Fluorobetaine copolymer and fire fighting foam concentrates therefrom

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- Number: US 2010/0168318 A1
- Document ID: US20100168318A1
- Status: Published application
- Kind: A1
- Application number: 12/531,757
- Filed: 2008-03-14
- Published: 2010-07-01
- Earliest claimed: 2007-03-21
- Assignees: E.I. du Pont de Nemours and Company
- Inventors: Romain Severac; Martial Jean-Jacques Pabon; Isabelle Deguerry; Guillaume Gamblin
- Web page: https://patentgrep.com/patent/US20100168318A1

## CPC

- C08F 214/18: Monomers containing fluorine
- C08F 214/20: Vinyl fluoride
- C08F 220/24: containing perhaloalkyl radicals
- C08F 220/387: {and containing nitrogen and oxygen}
- C08F: MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS

## Abstract

It has been discovered by in present invention that, compared with a fluorosurfactant having only one betaine group per molecule, a fluorosurfactant having a plurality of betaine groups per molecule is superior in its ability to undergo electrostatic interaction with other components of a fire fighting composition thereby improving the performance of the fire fighting composition. Previously known fluorosurfactants comprise only one betaine group per molecule. In contrast, the present invention provides for a fluorobetaine copolymer containing a plurality of betaine groups.

## Claims

### Claim 1

A fluorocopolymer comprising units represented by the following formula:
wherein Rf represents a perfluorinated alkyl group, optionally interrupted by oxygen, having at least 3 carbon atoms; each R1 is independently chosen from a C1-C20 hydrocarbylene; R8 is chosen from a C1-C20 hydrocarbyl or hydrogen; R2 is chosen from hydrogen, fluorine, or a C1-C4; s is 0 or 1; Y is benzyl or carbonyl, preferably carbonyl; RB is a group with the formula CaNbOcSfH2(a−e+b+1−2d having a structure which incorporates at least one betaine group of the formula (N+—CnH2n—CO2−) or (N+—CnH2n—SO3−) wherein a is an integer from 4-25, b is an integer from 1 to 4, c is an integer from 2 to 15, d is an integer from 0 to 3, e is an integer from 0 to 4, f is an integer from 0 to 4, the sum of e and f is from 1 to 4; n is independently chosen from an integer from 1 to 5; and R3 is chosen from hydrogen or a C1-C4 hydrocarbyl; and x is an integer from 1 to 10, y is an integer from 4 to 200, and the ratio of y:x is at least 1:1.

### Claim 2 (depends on 1)

The fluorocopolymer of claim 1 wherein s is 1.

### Claim 3 (depends on 1)

The fluoropolymer of claim 1 wherein Rf has from 1 to 6 carbon atoms; each R1 is independently a C1-C5 hydrocarbylene; R8 is chosen from C1-C5 hydrocarbyl or hydrogen; R2 is chosen from hydrogen or methyl; Y is carbonyl; R3 is chosen from hydrogen or methyl; and the ratio of y:x is at least 1:35.

### Claim 4 (depends on 1)

A method for making the fluorocopolymer of claim 1 comprising the steps of:
A) polymerizing monomers comprising at least one fluorinated acrylate monomer and at least one amino vinyl monomer represented respectively by Formula (1) and Formula (2) as follows:
wherein Rf represents a perfluorinated alkyl group, optionally interrupted by oxygen, having at least 3 carbon; each R1 is independently chosen from a C1-C20 hydrocarbylene, preferably C1-C5; R8 is chosen from a C1-C20 hydrocarbyl; R2 is chosen from hydrogen, fluorine, or a C1-C4 alkyl; R8 is chosen from a C1-C20 hydrocarbyl or hydrogen; RN is a group incorporating at least one tertiary amine said group having the formula CaNbOcH2a+b+1−2d where a is an integer from 3 to 20, b is a positive integer from 1 to 4, and c is an integer from 0 to 4, and d is an integer from 0 to 4; and Y is carbonyl or benzyl; and R3 is chosen from hydrogen or a C1-C4 hydrocarbyl; and
B) reacting the polymer obtained in step A) with at least one betaine forming compound chosen from:
i) an aliphatic halocarboxylic acid having the formula X-A-COOH wherein X is a halogen, A is a C1 to C4 alkylene;
ii) an aliphatic halosulfonic acid having the formula X-A-SO3H wherein X is a halogen; A is a C1 to C4 alkylene; or
iii) a lactone.

### Claim 5 (depends on 4)

The method of claim 4 wherein s is 1.

### Claim 6 (depends on 4)

The method of claim 4 wherein the aliphatic halocarboxylic acid or aliphatic halosulfonic acid is used in the form of its neutral alkaline earth metal salt.

### Claim 7 (depends on 1)

A fire fighting foam concentrate comprising the fluorocopolymer of claim 1.

### Claim 8 (depends on 7)

The fire fighting foam concentrate of claim 7 further comprising a polyethyleneimine.

### Claim 9 (depends on 7)

The fire fighting foam concentrate of claim 7 further comprising a hydrocarbon surfactant.

### Claim 10 (depends on 8)

The fire fighting foam concentrate of claim 8 further comprising a monobasic acid, polybasic acid or mixtures thereof

### Claim 11 (depends on 1)

The use of the fluorocopolymer of claim 1 as a fire fighting foam concentrate.