Formulation containing a metal aprotic organosilanoxide compound

Patent metadata

Field	Value
Publication number	US-10723914-B2
Application number	US-201716316073-A
Country	US
Kind code	B2
Filing date	Jun 7, 2017
Priority date	Jul 13, 2016
Publication date	Jul 28, 2020
Grant date	Jul 28, 2020

Abstract

A curable formulation containing a metal aprotic organosilanoxide compound of formula (I): {R 1 —Si(R 2 )(R 3 )—[O—Si(R 4 )(R 5 )] m —O} n- M 1 (←L) o (X 1 )p (I), wherein M 1 is a metal atom Al, Ce, Fe, Sn, Ti, V, or Zr, a polymerizable organosilicon compound, an organosilicon crosslinker for crosslinking the polymerizable organosilicon compound, and a silicon-based adhesion promoter. Also included is a cured product of curing the curable formulation; a manufactured article containing or prepared from the curable formulation or cured product; and methods of making and using the foregoing. The cured product may be free-standing or disposed on a substrate.

First claim

The invention claimed is:

1. A curable formulation comprising constituents (A), (B), (C) and (D):
(A) a metal aprotic organosilanoxide compound;
(B) a polymerizable organosilicon compound having on average, per molecule, at least 2 silicon-bonded unsaturated aliphatic groups;
(C) an organohydrogensilicon compound having on average, per molecule, at least two silicon-bonded hydrogen atoms; and
(D) an organosilicon adhesion promoter containing at least one silicon atom, at least 3 silicon-bonded aprotic leaving groups, and at least one silicon-bonded curable group other than a leaving group;
wherein the (A) metal aprotic organosilanoxide compound is of formula (I):
{R 1 —Si(R 2 )(R 3 )—[O—Si(R 4 )(R 5 )] m —O} n -M 1 (←L) o (X 1 ) p   (I),

wherein M 1 is a metal atom Al, Fe, Sn, or Zr having a formal positive oxidation state, δ + , of +1 to +3 for Al, +1 to +6 for Fe, +1 to +4 for Sn, subscript n is an integer from 1 to δ + ; subscript o is an integer of 0, 1 or 2; each L independently is an aprotic Lewis base; subscript p=(δ + −n); each X 1 independently is a halide or an aprotic organoheteryl anion; subscript m is an integer from 3 to 100; each of R 1 to R 5 is independently is an aprotic (C 1 -C 20 )hydrocarbyl group or aprotic (C 2 -C 20 ) heterohydrocarbyl group; provided that when M 1 is Zr, subscript n is δ + .

2. The curable formulation of claim 1 wherein none of R 1 to R 5 contain a carbon-carbon double or triple bond.

3. The curable formulation of claim 1 wherein at least one of R 1 to R 5 independently is an aprotic (C 2 -C 20 )alkenyl group or aprotic (C 2 -C 20 )alkynyl group.

4. The curable formulation of claim 1 wherein at least one M 1 is Al, Fe or Sn.

5. The curable formulation of claim 1 wherein subscript n is an integer from 2 to δ + .

6. The curable formulation of claim 1 wherein subscript o is an integer 0 or subscript o is an integer 1 or 2.

7. The curable formulation of claim 1 wherein subscript m is an integer from 3 to 50.

8. The curable formulation of claim 1 wherein the concentration of the (A) metal aprotic organosilanoxide compound of formula (I) is 0.01 to 10 weight percent (wt %) of the curable formulation.

9. The curable formulation of claim 1 wherein
the (B) polymerizable organosilicon compound is selected from an organosilane having on average, per molecule, 1 silicon atom and at least 2 unsaturated aliphatic groups; an oligoorganosiloxane having on average, per molecule, from 2 to 4 silicon atoms and at least 2 unsaturated aliphatic groups; a polyorganosiloxane having on average, per molecule, 5 or more silicon atoms and at least 2 unsaturated aliphatic groups; and a combination of any two or more thereof; or
the (C) organohydrogensilicon compound has on average, per molecule, from 1 to 100 silicon atoms and/or at least 2.2 silicon-bonded hydrogen atoms; or
in the (D) organosilicon adhesion promoter each silicon-bonded aprotic leaving group is independently a silicon-bonded aprotic alkoxy group, a silicon-bonded aprotic aliphatic carboxy group, a silicon-bonded aprotic dialkylamino group, a silicon-bonded halogen, or a silicon-bonded aprotic oximo group; and/or each silicon-bonded curable group other than a leaving group is independently an epoxy-functional hydrocarbyl group, a monovalent unsaturated aliphatic group that is free of an oxo (i.e., ═O) group, a monovalent unsaturated aliphatic carboxylic ester group, a monovalent isocyanate group, a monovalent aldehydic group (i.e., —C(═O)H), or a hybrid group of any two or more thereof; or
a combination of any two thereof.

10. The curable formulation of claim 1 further comprising one or more additional constituent other than the constituents (A) to (D), selected from (E) a cure agent; (F) an inhibitor of a hydrosilylation catalyst; (G) a filler; (H) a treating agent for treating the (G) filler; (I) a vehicle; (J) a colorant.

11. A cured product obtained by curing the curable formulation of claim 1 .

12. A method of making a cured product, the method comprising subjecting the curable formulation of claim 1 to a cure temperature from 30° to 250° C. to give the cured product.

Assignees

• Dow Silicones Corp

Inventors

• Liu Nanguo
• Rhodes Susan
• Shephard Nick Evan

Classifications

• C08G77/58

  Metal-containing linkages · CPC title

• C08K3/36

  Silica · CPC title

• C07F7/28

  Titanium compounds · CPC title

• C08K5/5415

  containing at least one Si—O bond · CPC title

• C08G77/20

  containing silicon bound to unsaturated aliphatic groups · CPC title