# US 10,501,657 B2 · Silicone coating composition containing surface sheen modifier

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- Number: US 10,501,657 B2
- Document ID: US10501657B2
- Status: Granted
- Kind: B2
- Application number: 15/453,291
- Filed: 2017-03-08
- Published: 2018-09-13
- Granted: 2019-12-10
- Earliest claimed: 2017-03-08
- Assignees: Momentive Performance Materials Inc.
- Applicants: Momentive Performance Materials Inc.
- Inventors: Gary Morgan Lucas
- Web page: https://patentgrep.com/patent/US10501657B2

## CPC

- C09D 183/04: Polysiloxanes
- C08K 3/22: of metals
- C08K 3/26: Carbonates; Bicarbonates
- C08K 9/04: Ingredients treated with organic substances {(treated with macromolecular compounds C08K9/08)}
- C09D 7/61: inorganic
- C09D 7/62: modified by treatment with other compounds
- C08G 77/16: to hydroxy groups
- C08K 2003/2241: {Titanium dioxide}
- C08K 2003/265: {Calcium, strontium or barium carbonate}
- C09D: COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR (cosmetics A61K; processes for applying liquids or other fluent materials to surfaces, in general, B05D; staining wood B27K5/02; glazes or vitreous enamels C03C; natural resins, French polish, drying-oils, driers, turpentine, per se, C09F; polishing compositions other than French polish, ski waxes C09G; adhesives or use of materials as adhesives C09J; materials for sealing or packing joints or covers C09K3/10; materials for stopping leaks C09K3/12; processes for the electrolytic or electrophoretic production of coatings C25D)
- C08K: Use of inorganic or non-macromolecular organic substances as compounding ingredients (paints, inks, varnishes, dyes, polishes, adhesives C09)
- C08G: MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS

## Abstract

There is provided herein an opaque one-part room temperature vulcanizing silicone polymer composition comprising: (a) a silanol-terminated diorganopolysiloxane, (b) an opaque reinforcing filler; (c) a polyalkoxysilane crosslinking agent; (d) a condensation cure catalyst; (e) an organo-functional alkoxy silane adhesion promoter; and, (f) a cyclic siloxane. There is also provided a method for the continuous production of such a silicone polymer composition, and a paint containing such a silicone polymer composition.

## Claims

### Claim 1

A paint selected from the group consisting of an acrylic paint, an acryl-silicone paint, a polyester paint, a urethane paint, a fluoride paint, a vinyl chloride paint, a latex paint, an acrylic-latex paint, and an alkyl paint, comprising an opaque one-part room temperature vulcanizing silicone polymer composition consisting essentially of:
(a) a silanol-terminated diorganopolysiloxane of the general formula (1):
wherein R1 and R2 are independently monovalent hydrocarbon radicals containing up to about 12 carbon atoms, and the subscript n is of such a value that the viscosity of the silanol-terminated diorganopolysiloxane is from 50 to 1,000,000 cps;
(b) an opaque reinforcing filler which is selected from the group consisting of untreated or stearic acid-treated ground, precipitated or colloidal calcium carbonates, alumina, aluminum hydroxide, titanium hydroxide, clays, diatomaceous earth, iron oxide, carbon black, graphite and combinations thereof;
(c) a polyalkoxysilane crosslinking agent of the general formula (2):
(R1O)4-a(R2)aSi (2)
wherein R1 and R2 are as defined and the subscript a is 0 or 1;
(d) a condensation cure catalyst;
(e) an organo-functional alkoxy silane adhesion promoter of the general formula (6)
(R10O)3-a(R11)aSiX (6)
wherein R10 and R11 are independently monovalent hydrocarbon radicals containing up to about 12 carbon atoms, and subscript a is as defined, and X is an organo group of up to 12 carbon atoms; and,
(f) a cyclic siloxane of the general formula (7):
wherein R12 and R13 are independently linear or branched alkyl radicals of from 1 to 4 carbon atoms, and the subscript x is from about 3 to about 10; and, wherein the composition is in the absence of silica-based matting agents, and wherein the silicone polymer composition is present in an amount of from about 1 to about 50 weight percent of the paint composition.

### Claim 2 (depends on 1)

The paint of claim 1 wherein R1 and R2 of the silanol-terminated polydimethylsiloxane (a) of the general formula (I) are each independently methyl or ethyl and the subscript n is from about 300 to about 4,000.

### Claim 3 (depends on 1)

The paint of claim 1 wherein R1 of the polyalkoxysilane crosslinking agent (c) of the general formula (2) is a linear or branched hydrocarbon radical containing up to about 4 carbon atoms and the subscript a is 0.

### Claim 4 (depends on 1)

The paint of claim 1 wherein the condensation cure catalyst (d) is of the general formula (3):
wherein Me is a metal selected from the group consisting of lead, tin, zirconium, antimony, iron, cadmium, barium, manganese, zinc, cobalt, nickel, aluminum, gallium, geranium and titanium, the subscripts is from about 0.7 to about 1.3, and the subscript t is from 0.8 to 1.2, R7 is a divalent hydrocarbon radical containing from 2 to about 20 carbon atoms, optionally substituted with a hydrocarbon group containing up to 8 carbon atoms, R3 is hydrogen or an organic radical selected from the group consisting of hydrocarbyl, halohydrocarbyl and acyl each containing up to 8 carbon atoms, R4 is the same as R3 or part of a cyclic hydrocarbon group formed by a bond to a carbon atom of the adjacent R3 and/or R5 groups wherein the cyclic hydrocarbon group contains up to 12 carbon atoms, and optionally substituted with one or more functional groups selected from the group consisting of chloro, nitro, ester, cyano, and carboxy ester substituents, R5 is defined the same as R3; R6 is a monovalent organic radical selected from the group consisting of hydrocarbyl, halohydrocarbyl and ether containing up to 60 carbon atoms, cyanoalkyl containing up to 12 carbon atoms, amino and polyether groups of the formula (CqH2qO)vR8, where q is from 2 to 4, and v is from 1 to 20, and R8 is a monovalent hydrocarbon radical of from 1 to 30 carbon atoms.

### Claim 5 (depends on 1)

The paint of claim 1 wherein the condensation cure catalyst (d) is of the general formula (4):
wherein R9 is methyl or —OC2H5.

### Claim 6 (depends on 1)

The paint of claim 1 wherein the condensation cure catalyst (d) is of the formula (5):

### Claim 7 (depends on 1)

The paint of claim 1 wherein the organo-functional alkoxy silane adhesion promoter (e) of the general formula (6) is selected from the group consisting of methacryloxypropyltrimethoxysilane, glycidoxypropylethyldimethoxysilane, γ-glycidoxypropyltrimethoxysilane, γ-glycidoxyethyltrimethoxysilane, β-(3,4-epoxycyclohexyl)propyltrimethoxysilane, β-(3,4-epoxycyclohexyl) ethylmethyldimethoxysilane, isocyanatopropyltriethoxysilane, isocyanatopropylmethyldimethoxysilane, β-cyanoethyltrimethoxysilane, γ-acryloxypropyltrimethoxysilane, γ-methacryloxypropylmethyldimethoxysilane, n-2-aminoethyl-3-aminopropyltrimethoxysilane, n-2-aminoethyl-3-aminopropyltriethoxysilane, γ-aminopropyltriethoxysilane, γ-aminopropyltrimethoxysilane, aminopropyltrimethoxysilane, N-Phenyl-γ-aminopropyltrimethoxysilane, triaminofunctionaltrimethoxysilane, γ-aminopropylmethyldiethoxysilane, γ-aminopropylmethyldiethoxysilane, methylaminopropyltrimethoxysilane and combinations thereof.

### Claim 8 (depends on 1)

The paint of claim 1 wherein the cyclic siloxane of the general formula (7) is selected from the group consisting of hexamethylcyclotrisiloxane, octamethylcyclotetrasiloxane, dodecamethylcyclohexasiloxane and combinations thereof.

### Claim 9 (depends on 1)

The paint of claim 1 further comprising at least one of a pigment, plasticizer, thixotrope, antioxidant, ultraviolet stabilizer, moisture scavenger, surfactant, solvent or biocide.

### Claim 10 (depends on 1)

The paint of claim 1 which has a VOC level not exceeding about 50 gm/L.

### Claim 11 (depends on 1)

The paint of claim 1 having a gloss level of from about 4 to about 80 as measured by a 60° angle KSM MG-6-S1 gloss meter.

### Claim 12 (depends on 1)

The paint of claim 1 having a semi-gloss, satin or matte appearance.

### Claim 13 (depends on 1)

The paint of claim 1 having a gloss level of from about 15 to about 70 as measured by a 60° angle KSM MG-6-S1 gloss meter.

### Claim 14 (depends on 1)

The paint of claim 1 wherein the paint is an exterior silicone trim paint.

### Claim 15 (depends on 1)

A method for the continuous production of the paint of claim 1 consisting essentially of:
(I) mixing a silanol-terminated organopolysiloxane (a) and reinforcing filler (b) in a densifier;
(II) adding the mixed contents of the densifier to an extruder apparatus;
(III) adding the polyalkoxysilane crosslinking agent (c), condensation cure catalyst (d), organo-functional alkoxy silane adhesion promoter (e) and cyclic siloxane (f) to the extruder apparatus at a point downstream of the addition step (II);
(IV) extruding the contents of step (III); and,
(V) applying a de-airing vacuum at a point following step (III) but prior to step (IV) or at a point during and/or after step (IV) to produce the silicone polymer composition of claim 1,
wherein steps (I)-(V) are conducted for a period of time sufficient to repeat steps (I)-(V) at least twice, and adding the silicone polymer composition to a paint composition to form a paint composition comprising the silicone polymer composition.

### Claim 16 (depends on 15)

The paint produced by the method of claim 15, wherein the paint has a VOC level not exceeding about 50 g/L.

### Claim 17 (depends on 15)

The method of claim 15 wherein the paint composition has a gloss appearance of semi-gloss, satin or matte.

### Claim 18 (depends on 15)

The method of claim 15 wherein the paint composition has a gloss level of from about 4 to about 80 as measured by a 60° angle KSM MG-6-S1 gloss meter.

### Claim 19 (depends on 1)

The paint of claim 1 wherein the paint is a silicone exterior paint.