IP Library Granted Patent US 8,420,826
Granted Patent B2
US 8,420,826 · App. 13/242,365 · Granted Apr 16, 2013

Fluoroalkyl silanes

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Quick Facts
Patent No.
US 8,420,826
App. No.
13/242,365
Granted
Apr 16, 2013
Kind
B2
Abstract

The present invention is directed to a fluorosilane represented by (L) 3 -Si—(CH 2 ) n —(Z 1 ) a —[C(X 1 )] x —(Z 2 ) l -Q 1 -R f where each n is independently an integer from 1 to 12; L is independently chosen from a hydrolysable or non-hydrolysable monovalent group; R f is chosen from a C 2 -C 12 perfluoroalkyl provided that: i) one fluorine atom of the perfluoroalkyl can be optionally replaced by hydrogen, and/or ii) the perfluoroalkyl can be optionally interrupted by at least one oxygen, methylene, or ethylene; Q 1 is chosen from the group consisting of a C 2 -C 12 hydrocarbylene optionally interrupted by at least one divalent organic group; X 1 is chosen from O or S; —Z 2 is —NH— and Z 1 is from the group consisting of —O—, and —S—; each R 1 is independently chosen from hydrogen, phenyl, or a monovalent C 1 -C 8 alkyl optionally terminated by —C 6 H 5 , preferably H or CH 3 .

Claims (34)

1. A fluorosilane represented by

(L) 3 -Si—(CH 2 ) n —(Z 1 ) a —[C(X 1 )] x —(Z 2 ) l -Q 1 -R f   Formula 1

wherein:

each n is independently an integer from 1 to 12;

L is independently chosen from a hydrolysable or non-hydrolysable monovalent group

R f is chosen from a C 2 -C 12 perfluoroalkyl provided that: i) one fluorine atom of the perfluoroalkyl can be optionally replaced by hydrogen, and/or ii) the perfluoroalkyl can be optionally interrupted by at least one oxygen, methylene, or ethylene;

Q 1 is chosen from the group consisting of a C 2 -C 12 hydrocarbylene optionally interrupted by at least one divalent organic group;

X 1 is chosen from O or S;

Z 2 is —NH— and Z 1 is from the group consisting of —O—, and —S—;

each R 1 is independently chosen from hydrogen, phenyl, or a monovalent C 1 -C 8 alkyl optionally terminated by —C 6 H 5 , preferably H or CH 3 .

2. The fluorosilane of claim 1 being an isocyanate derived fluorosilane wherein:

a=1, x=1, and l=1;

Z 2 is —NH— and Z 1 is from the group consisting of —O—, and —S—;

said isocyanate derived fluorosilane represented by the formula:

(L) 3 -Si—(CH 2 ) n —Z 1 —C(X 1 )—Z 2 -Q 1 -R f ;

provided that when Z 1 is O, Q 1 is a C 2 -C 12 hydrocarbylene interrupted by at least one divalent moiety chosen from the group consisting of —S—, —S(O)—, —S(O) 2 —, —NH—S(O) 2 —, —N(CH) 3 S(O) 2 —, and

3. The isocyanate derived fluorosilane of claim 2 being a carbamate fluorosilane wherein:

Z 1 is —O— and Z 2 is —NH—; and

X 1 is O;

said carbamate represented by the formulae:

(L) 3 Si—(CH 2 ) n —O—C(O)—NH-Q 1 -R f

wherein:

Q 1 is a C 2 -C 12 hydrocarbylene optionally interrupted by at least one divalent moiety chosen from the group consisting of —NH—C(O)—NH—, —NH—C(S)—NH—, —S—, —S(O)—, —S(O) 2 —, —(R 1 )N—S(O) 2 —,

4. The carbamate fluorosilane of claim 3 wherein R f is chosen from a C 2 -C 12 perfluoroalkyl and Q 1 is independently chosen from the group consisting of a C 2 -C 12 hydrocarbylene interrupted by at least one divalent moiety chosen from the group consisting of —S—, —S(O)—, —S(O) 2 —, and —O—C(O)—NH—.

5. The carbamate fluorosilane of claim 3 wherein R f is chosen from a C 2 -C 12 perfluoroalkyl provided that: i) one fluorine atom of the perfluoroalkyl is replaced by hydrogen, and/or ii) the perfluoroalkyl is interrupted by at least one oxygen, methylene, or ethylene; Q is chosen from the group consisting of a C 2 -C 12 hydrocarbylene optionally interrupted by at least one divalent organic group.

6. The isocyanate derived fluorosilane of claim 2 being a thiolcarbamate fluorosilane wherein:

Z 1 is —S— and Z 2 is —NH—; and

X 1 is O;

said thiolcarbamate fluorosilane represented by the formulae:

(L) 3 Si—(CH 2 ) n —S—C(O)—NH-Q 1 -R f

wherein:

Q 1 is independently chosen from the group consisting of a C 2 -C 12 hydrocarbylene optionally interrupted by at least one divalent moiety chosen from the group consisting of —S—, —S(O)—, —S(O) 2 —, —N(R 1 )—C(O)—, —C(O)—N(R 1 )—, —(R 1 )N—S(O) 2 —, and

7. The thiolcarbamate fluorosilane of claim 6 wherein R f is chosen from a C 2 -C 12 perfluoroalkyl and Q 1 is independently chosen from the group consisting of a C 2 -C 12 hydrocarbylene interrupted by at least one divalent moiety chosen from the group consisting of —S—, —S(O)—, —S(O) 2 —, and —O—C(O)—NH —.

8. The thiolcarbamate fluorosilane of claim 6 wherein R f is chosen from a C 2 -C 12 perfluoroalkyl provided that: i) one fluorine atom of the perfluoroalkyl is replaced by hydrogen, and/or ii) the perfluoroalkyl is interrupted by at least one oxygen, methylene, or ethylene; Q is chosen from the group consisting of a C 2 -C 12 hydrocarbylene optionally interrupted by at least one divalent organic group.

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 →