IP Library Granted Patent US 9,464,160
Granted Patent B2
US 9,464,160 · App. 12/869,897 · Granted Oct 11, 2016

Fluorinated ethoxylated polyurethanes

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Quick Facts
Patent No.
US 9,464,160
App. No.
12/869,897
Granted
Oct 11, 2016
Kind
B2
Abstract

The present invention comprises fluorinated ethoxylated polyurethanes of formula [R f —(X) n —(CH 2 CHR 1 —O) m —CH 2 CH 2 —O—C(O)—NH] p -A, wherein R f is a C 1 to C 6 perfluoroalkyl; X is a divalent radical; n is 0 or 1; R1 is H or C 1 to C 4 alkyl; m is 1 to 20; p is a positive integer of at least 2; and A is the residue of a polyisocyanate, and methods for altering surface behavior of liquids using such compounds.

Claims (18)

1. A composition comprising a compound of Formula 1, where the compounds present fitting Formula 1 have no reaction in the composition;

[R f —(X) n —(CH 2 CHR 1 —O) m —CH 2 CH 2 —O—C(O)—NH] p -A  Formula 1

wherein

R f is a C 1 to C 6 perfluoroalkyl;

X is —O—, —CH 2 O—, —CH 2 —,

—CH 2 CH 2 O—, or —S(O) 2 N(R 2 )CH 2 CH 2 O— wherein R 2 is C 1 to C 4 alkyl;

n is 0 or 1;

R1 is H or C 1 to C 4 alkyl;

m is 1 to 20;

p is a positive integer of at least 2; and

A is the residue of a polyisocyanate selected from the group consisting of a hexamethylene diisocyanate, hexamethylene diisocyanate trimer, hexamethylene diisocyanate homopolymer; isophorone diisocyanate; hydrocarbon diisocyanate-derived isocyanurate trimers; isocyanurate trimer of toluene diisocyanate; isocyanurate trimer of 3-isocyanatomethyl-3,4,4-trimethylcyclohexyl isocyanate; methane-tris-(phenylisocyanate); bis-(4-isocyanatocyclohexyl)methane; 2,4-toluene diisocyanate; 2,6-toluene diisocyanate; diphenylmethane 4,4′-diisocyanate; diphenylmethane 2,4′-diisocyanate; 3-isocyanatomethyl-3,4,4-trimethylcyclohexyl isocyanate; bis-(4-isocyanatocyclohexyl)methane and diisocyanate trimers of formula (IIa), (IIb), (IIc), and (IId):

wherein the residue contains no active isocyanate groups;

wherein the compound is the reaction product of reagents consisting essentially of a fluorinated alcohol of Formula 2

[R f —(X) n —(CH 2 CHR 1 —O) m —CH 2 CH 2 —OH  Formula 2

and a polyisocyanate, where R f , X, n, R 1 , and m are defined as above.

2. The compound of claim 1 wherein R f is a C 4 to C 6 perfluoroalkyl.

3. The compound of claim 2 wherein A is a residue of isophorone diisocyanate, hexamethylene diisocyanate, hexamethylene diisocyanate trimer, or a diisocyanate trimer of formula (IIa), (IIb), (IIc), and (IId):

4. The compound of claim 2 wherein X is —CH 2 CH 2 O—.

Assignments (4)
RELEASE OF SECURITY INTEREST Recorded Apr 4, 2018
From: JPMORGAN CHASE BANK, N.A., AS ADMINISTRATIVE AGENT
To: THE CHEMOURS COMPANY FC, LLC
Reel/Frame 045845/0913 →
SECURITY INTEREST Recorded Apr 4, 2018
From: THE CHEMOURS COMPANY FC, LLC
To: JPMORGAN CHASE BANK, N.A., AS ADMINISTRATIVE AGENT
Reel/Frame 045846/0011 →
SECURITY AGREEMENT Recorded Jun 10, 2015
From: THE CHEMOURS COMPANY FC LLC; THE CHEMOURS COMPANY TT, LLC
To: JPMORGAN CHASE BANK, N.A.
Reel/Frame 035839/0675 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Apr 15, 2015
From: E. I. DU PONT DE NEMOURS AND COMPANY
To: THE CHEMOURS COMPANY FC, LLC
Reel/Frame 035432/0023 →