Fluorinated ethoxylated polyurethanes

• US 9,464,160 B2
• Filed: 08/27/2010
• Issued: 10/11/2016
• Est. Priority Date: 08/27/2010
• Status: Active Grant

• Current Assignee: The Chemours Company FC, LLC (The Chemours Company)
• Original Assignee: The Chemours Company FC, LLC (The Chemours Company)
• Inventors: Ober, Michael Henry, Kanetsky, Kathleen L., Yake, Allison Mary
• Primary Examiner(s): RICCI, CRAIG D
• Application Number:
  US12/869,897
• Publication Number:
  US 20120053252A1
• Time in Patent Office: 2,237 Days
• Field of Search: None
• US Class Current: 1/1
• CPC Class Codes: C08G 18/2885 containing halogen atoms
• CPC Class Codes: C08G 18/73 acyclic
• CPC Class Codes: C08G 18/755 and at least one isocyanate or isothiocyanate group linked to a secondary carbon atom of the cycloaliphatic ring, e.g. isophorone diisocyanate
• CPC Class Codes: C08G 18/7831 containing biuret groups
• CPC Class Codes: C08G 18/792 formed by oligomerisation of aliphatic and/or cycloaliphatic isocyanates or isothiocyanates
• CPC Class Codes: C09K 13/00 Etching, surface-brightening or pickling compositions for glass C03C15/00, C03C25/66; for mortars, concrete, artificial or natural stone or ceramics C04B41/5338 ; for metallic material C23F, C23G1/00, C25F1/00; for semi-conductors H01L
• CPC Class Codes: C09K 8/035 Organic additives
• CPC Class Codes: C09K 8/52 Compositions for preventing, limiting or eliminating depositions, e.g. for cleaning
• CPC Class Codes: C09K 8/602 containing surfactants
• CPC Class Codes: C09K 8/68 containing organic compounds
• CPC Class Codes: C11D 3/3726 Polyurethanes

Abstract

The present invention comprises fluorinated ethoxylated polyurethanes of formula [R_f—(X)_n—(CH₂CHR¹—O)_m—CH₂CH₂—O—C(O)—NH]_p-A, wherein R_f is a C₁ to C₆ perfluoroalkyl; X is a divalent radical; n is 0 or 1; R1 is H or C₁ to C₄ 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

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—

(CH₂CHR¹—

O)_m—

CH₂CH₂—

O—

C(O)—

NH]_p-A 

 

Formula 1

wherein

R_f is a C₁ to C₆ perfluoroalkyl;

X is —

O—

, —

CH₂O—

, —

CH₂—

,

—

CH₂CH₂O—

, or —

S(O)₂N(R²)CH₂CH₂O—

wherein R² is C₁ to C₄ alkyl;

n is 0 or 1;

R1 is H or C₁ to C₄ 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);

2. The compound of claim 1 wherein R_f is a C₄ to C₆ 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 —

CH₂CH₂O—

.