Composition including polysiloxane phosphate or phosphonate and method of making a treated article

Patent metadata

Field	Value
Publication number	US-2022017779-A1
Application number	US-201917414828-A
Country	US
Kind code	A1
Filing date	Dec 17, 2019
Priority date	Dec 18, 2018
Publication date	Jan 20, 2022
Grant date	—

Abstract

The composition includes a polysiloxane having at least one of a phosphate or phosphonate group and an amino-functional compound having at least one silane group. The method includes treating the metal surface with a composition including a polysiloxane functionalized with at least one of a phosphate or phosphonate group. The method can include first treating the metal surface with a primer composition including an amino-functional compound having at least one silane group or including an amino-functional compound having at least one silane group in the composition with the polysiloxane. Certain polysiloxanes functionalized with at least one of a phosphate or phosphonate group are also described.

First claim

1 . (canceled)

2 . A method of making a treated article having a metal surface, the method comprising treating at least a portion of the metal surface with a composition comprising a polysiloxane functionalized with at least one of a phosphate or phosphonate group, wherein the polysiloxane comprises first divalent units independently represented by formula:

and at least one of
a second divalent unit represented by formula:

or
a terminal unit represented by formula —R 1 -Q′-(Z) z or —R 1 —(S) y —W;
wherein
each R is independently alkyl having up to 8 carbon atoms, haloalkyl having up to 8 carbon atoms, alkenyl having up to 8 carbon atoms, phenyl that is unsubstituted or substituted by at least one alkyl or alkoxy having up to 4 carbon atoms or halogen, or benzyl that is unsubstituted or substituted by at least one alkyl or alkoxy having up to 4 carbon atoms or halogen;
each R 1 is independently alkylene, arylene, or alkylene interrupted or terminated by arylene;
each Q is independently a bond, alkylene, arylalkylene, alkylarylene, or arylene, wherein the alkylene, arylalkylene, alkylarylene, and arylene are optionally at least one of interrupted or terminated by at least one ether, thioether, amine, amide, ester, thioester, carbonate, thiocarbonate, carbamate, thiocarbamate, urea, thiourea, or a combination thereof;
each Q′ is independently a bond or divalent or multivalent alkylene, arylalkylene, alkylarylene, or arylene, wherein the divalent or multivalent alkylene, arylalkylene, alkylarylene, and arylene are optionally at least one of interrupted or terminated by at least one ether, thioether, amine, amide, ester, thioester, carbonate, thiocarbonate, carbamate, thiocarbamate, urea, thiourea, or a combination thereof;
y is 0 or 1;
z is 1 or 2;
each W independently comprises divalent units represented by formula

 or a combination thereof;
each R′ is independently hydrogen or methyl;
each G is independently selected from the group consisting of —O—, —S—, and —N(R 11 )—;
each R 11 is independently selected from the group consisting of hydrogen and alkyl having from 1 to 4 carbon atoms;
each V is independently alkylene that is optionally interrupted by at least one ether linkage or amine linkage;
each Z is independently —P(O)(OM) 2 or —O—P(O)(OM) 2 ; and
each M is independently hydrogen, alkyl, trialkylsilyl, a counter cation, or a bond to the metal surface.

3 . The method of claim 2 , wherein the polysiloxane comprises the second divalent unit represented by formula:

wherein
each R 1 is independently alkylene;
each Q is independently a bond or alkylene optionally at least one of interrupted or terminated by at least one ether or thioether; and
Z is —P(O)(OM) 2 or —O—P(O)(OM) 2 , wherein each M is independently hydrogen, a counter cation, or a bond to the metal surface.

4 . The method of claim 2 , wherein the polysiloxane comprises one or two terminal units represented by formula —R 1 -Q′-(Z) z ;
wherein
each R 1 is independently alkylene;
each Q′ is independently a bond or divalent alkylene optionally at least one of interrupted or terminated by at least one ether, thioether, amine, ester, or combination thereof;
Z is —P(O)(OM) 2 or —O—P(O)(OM) 2 , wherein each M is independently hydrogen, a counter cation, or a bond to the surface; and
z is 1.

5 . The method of claim 2 , wherein the polysiloxane has a number average molecular weight of at least 900 grams per mole.

6 . The method of claim 2 , wherein the composition further comprises an amino-functional compound having at least one silane group, wherein amino-functional compound is represented by formula:
(R 6 ) 2 N—[R 4 —Z′] a —R 4 —[Si(X) b (R 5 ) 3-b ]
wherein
R 4 is arylene or alkylene optionally interrupted or terminated by arylene;
each Z′ is independently —O— or —NR 6 —;
R 5 is alkyl, aryl, or alkylenyl interrupted or terminated by aryl;
each R 6 is independently hydrogen, alkyl, aryl, arylalkylenyl, or —R 4 —[Si(Y) p (R 5 ) 3-p ];
each X is independently hydroxyl, alkoxy, acetoxy, aryloxy, or halogen;
a is 0, 1, 2, or 3; and
b is 1, 2, or 3.

7 . The method of claim 2 , further comprising:
treating the metal surface with a primer composition comprising an amino-functional compound having at least one silane group to provide a primed metal surface before treating the metal surface with a composition comprising a polysiloxane having at least one of a phosphate or phosphonate group, wherein the amino-functional compound having at least silane group is represented by formula:
(R 6 ) 2 N—[R 4 —Z′] a —R 4 —[Si(X) b (R 5 ) 3-b ]

wherein
each R 4 is independently arylene or alkylene optionally interrupted or terminated by arylene;
each Z′ is independently —O— or —NR 6 —;
R 5 is alkyl, aryl, or alkylenyl interrupted or terminated by aryl;
each R 6 is independently hydrogen, alkyl, aryl, arylalkylenyl, or —R 4 —[Si(Y) p (R 5 ) 3-p ];
each X is independently hydroxyl, alkoxy, acetoxy, aryloxy, or halogen;
a is 0, 1, 2, or 3; and
b is 1, 2, or 3.

8 . The method of claim 6 , wherein the amino-functional compound having at least one silane group is bis(3-trimethoxysilylpropyl)amine, N-methyl-bis(3-trimethoxysilylpropyl)amine, N,N′-bis[3-trimethoxysilylpropyl]-ethylenediamine, bis(3-triethoxysilylpropyl)amine, N-methyl-bis(3-triethoxysilylpropyl)amine, N,N′-bis[3-triethoxysilylpropyl]-ethylenediamine, or a combination thereof.

9 . The method of claim 2 , wherein the metal surface comprises at least one of chromium, chromium alloys, iron, aluminum, copper, nickel, titanium, zinc, tin, stainless steel, mild steel, or brass.

10 . A composition comprising:
a polysiloxane having at least one of a phosphate or phosphonate group; and an amino-functional compound having at least one silane group.

11 . The composition of claim 10 , wherein the polysiloxane comprises first divalent units independently represented by formula:

and at least one of
a second divalent unit represented by formula:

 or
a terminal unit represented by formula —R 1 -Q′-(Z) z or —R 1 —(S) y —W;
wherein
each R is independently alkyl having up to 8 carbon atoms, haloalkyl having up to 8 carbon atoms, alkenyl having up to 8 carbon atoms, phenyl that is unsubstituted or substituted by at least one alkyl or alkoxy having up to 4 carbon atoms or halogen, or benzyl that is unsubstituted or substituted by at least one alkyl or alkoxy having up to 4 carbon atoms or halogen;
each R 1 is independently alkylene, arylene, or alkylene interrupted or terminated by arylene;
each Q is independently a bond, alkylene, arylalkylene, alkylarylene, or arylene, wherein the alkylene, arylalkylene, alkylarylene, and arylene are optionally at least one of interrupted or terminated by at least one ether, thioether, amine, amide, ester, thioester, carbonate, thiocarbonate, carbamate, thiocarbamate, urea, thiourea, or a combination thereof;
each Q′ is indep

Assignees

• 3M Innovative Properties Co

Inventors

• Audenaert Frans A
• Fan Wayne W
• Nuyts Inge
• Colak Atan Semra
• Sgolastra Federica
• Griesgraber George W

Classifications

• C09D183/08 Primary

  containing silicon bound to organic groups containing atoms other than carbon, hydrogen, and oxygen · CPC title

• C08G77/30

  phosphorus-containing groups · CPC title

• B05D2202/15

  Stainless steel · CPC title

• B05D1/18

  performed by dipping · CPC title

• C08K5/544

  containing nitrogen · CPC title