Composition including silanes and methods of making a treated article

Patent metadata

Field	Value
Publication number	US-10858540-B2
Application number	US-201615762350-A
Country	US
Kind code	B2
Filing date	Sep 21, 2016
Priority date	Sep 23, 2015
Publication date	Dec 8, 2020
Grant date	Dec 8, 2020

Abstract

A composition that includes an amino-functional compound having at least one silane group, a fluorinated compound represented by formula Rf{—X—[Si(Y) 3-x (R) x ] y } z , and a non-fluorinated organic solvent having a flashpoint of at least 40° C. A method of making a treated article having a metal surface using a composition that includes an amino-functional compound having at least one silane group, a fluorinated compound represented by formula Rf{—X—[Si(Y) 3-x (R) x ] y } z , and an organic solvent having a flashpoint of at least 40° C. is also disclosed. Another method includes treating the metal surface with a primer composition including an amino-functional compound having at least one silane group to provide a primed metal surface and subsequently treating the primed metal surface with a treatment composition including a fluorinated compound represented by formula Rf{—X—[Si(Y) 3-x (R) x ] y } z . The compositions each include up to one percent by weight of an organic solvent having a flashpoint up to 40° C.

First claim

What is claimed is:

1. A composition comprising;
an amino-functional compound having at least one silane group;
a fluorinated compound represented by formula:
Rf{—X—[Si(Y) 3-x (R) x ] y } z

wherein:
Rf is a polyfluoropolyether group;
X is a divalent or trivalent organic linking group;
each Y is independently halogen, alkoxy, hydroxyl, acyloxy, polyalkyleneoxy, or aryloxy;
R is an alkyl group having up to 8 carbon atoms or a phenyl group;
x is 0 or 1 or 2;
y is a value from 1 to 8; and
z is 1 or 2; and

a non-fluorinated organic solvent having a flashpoint of at least 40° C.,

wherein the composition comprises up to one percent by weight of an organic solvent having a flashpoint up to 40° C. and up to five percent by weight of an hydrofluoroether having a flashpoint of at least 40° C.

2. A composition comprising;
an amino-functional compound having at least one silane group;
a fluorinated compound represented by formula:
Rf{—X—[Si(Y) 3-x (R) x ] y } z

wherein:
Rf is a polyfluoropolyether group;
X is a divalent or trivalent organic linking group;
each Y is independently halogen, alkoxy, hydroxyl, acyloxy, polyalkyleneoxy, or aryloxy;
R is an alkyl group having up to 8 carbon atoms or a phenyl group;
x is 0 or 1 or 2;
y is a value from 1 to 8; and
z is 1 or 2; and

a non-fluorinated organic solvent having a flashpoint of at least 40° C.,

wherein the composition comprises up to one percent by weight of an organic solvent having a flashpoint up to 40° C., and wherein the fluorinated compound is present in the composition in an amount up to 0.4 percent by weight, based on the total weight of the composition.

3. The composition of claim 2 , wherein the fluorinated compound is represented by formula
Rf{Q-X′—[Si(Y) 3-x (R) x ] y } z , wherein

Q is a bond, —C(O)—N(R′)—, —C(O)—O—, or —SO 2 N(R′)—, wherein R′ is hydrogen or alkyl having up to 4 carbon atoms; and
X′ is a divalent or trivalent organic linking group comprising at least one of alkylene or arylalkylene, each of which is optionally interrupted by at least one functional group that is independently ether, thioether, sulfone, amine, ester, amide, carbamate, or urea.

4. The composition of claim 3 , wherein Q is —C(O)—N(R′)—, and X′ is divalent or trivalent alkylene that is optionally interrupted by at least one functional group that is independently ether, ester, carbamate, or urea.

5. The composition of claim 1 , wherein the amino-functional compound is a secondary or tertiary amino-functional compound having at least two independently selected silane groups.

6. The composition of claim 5 , wherein the secondary or tertiary amino-functional compound is represented by formula
(R 3 ) 2 N—R 1 —[Si(Y) p (R 2 ) 3-p ] q

wherein
R 1 is a multivalent alkylene group optionally interrupted by one or more —O— groups or up to three —NR 3 — groups;
R 2 is alkyl or arylalkylenyl;
each R 3 is independently hydrogen, alkyl, arylalkylenyl, or —R 1 —[Si(Y) p (R 2 ) 3-p ];
Y is alkoxy, acyloxy, aryloxy, polyalkyleneoxy, halogen, or hydroxyl;
p is 1, 2, or 3; and
q is 1, 2, or 3,

with the provisos that at least two independently selected —Si(Y) p (R 2 ) 3-p groups are present and that both R 3 groups may not be hydrogen.

7. The composition of claim 6 , wherein one R 3 is alkyl or hydrogen, and the other R 3 is —R 1 —[Si(Y) p (R 2 ) 3-p ].

8. The composition of claim 1 , wherein Rf comprises perfluorinated repeating units comprising at least one of —(C n F 2n O)—, —(CF(Z)O)—, —(CF(Z)C n F 2n O)—, or —(C n F 2n CF(Z)O)—; and wherein Z is a perfluoroalkyl group or a perfluoroalkoxy group, each of which is optionally interrupted by at least one ether linkage, and n is an integer from 1 to 12.

9. The composition of claim 8 , wherein z is 2, and Rf is —CF 2 O(CF 2 O) m (C 2 F 4 O) b CF 2 —, —CF 2 O(C 2 F 4 O) b CF 2 —, —(CF 2 ) 3 O(C 4 F 8 O) b (CF 2 ) 3 —, or —CF(CF 3 )—(OCF 2 CF(CF 3 )) b O—Rf′—O(CF(CF 3 )CF 2 O) b CF(CF 3 )—, and wherein Rf′ is a perfluoroalkylene group optionally interrupted by at least one ether or amine linkage, m is 1 to 50, and b is 3 to 40.

10. The composition of claim 1 , wherein Rf is C 3 F 7 O(CF(CF 3 )CF 2 O) a CF(CF 3 )—, C 3 F 7 O(CF 2 CF 2 CF 2 O) a CF 2 CF 2 —, or CF 3 O(C 2 F 4 O) a CF 2 —, wherein “a” has an average value of 3 to 50, and wherein z is 1.

11. The composition of claim 2 , further comprising a hydrofluoroether having a flashpoint of at least 40° C.

12. The composition of claim 1 , wherein the composition is essentially free of an acid catalyst.

13. A method of making a treated article having a metal surface, the method comprising treating the metal surface with the composition of claim 1 .

14. A method of making a treated article having a metal surface, the method comprising treating the metal surface with the composition of claim 2 .

15. The method of claim 13 , wherein the metal surface comprises at least one of chromium, chromium alloys, iron, aluminum, copper, nickel, zinc, tin, stainless steel, or brass.

16. The composition of claim 3 , wherein X′ is

17. The composition of claim 1 , wherein the amino-functional compound is bis(3-trimethoxysilylpropyl)amine, N-methyl-bis(3-trimethoxysilylpropyl)amine, or N,N′-bis[3-trimethoxysilylpropyl]-ethylenediamine.

18. The composition of claim 1 , wherein y is 1 or 2.

19. The composition of claim 1 , wherein the amino-functional compound is present in the composition in a range from 0.01 percent to 2 percent by weight, based on the total weight of the composition.

20. The composition of claim 1 , wherein the fluorinated compound is present in the composition in an amount less than 0.4 percent by weight, based on the total weight of the composition.

Assignees

• 3M Innovative Properties Co

Inventors

• Audenaert Frans A
• Schuell Christoph T R
• Nuyts Inge

Classifications

• B05D2518/10

  Silicon-containing polymers · CPC title

• C23C2222/20

  Use of solutions containing silanes · CPC title

• C08G77/26

  nitrogen-containing groups · CPC title

• C08G77/24

  halogen-containing groups · CPC title

• B05D2506/10

  Fluorinated polymers · CPC title