# US 5,708,046 A · Silicone release coating compostions

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- Number: US 5,708,046 A
- Document ID: US5708046A
- Status: Granted
- Kind: A
- Application number: 08/716,981
- Filed: 1996-09-20
- Granted: 1998-01-13
- Earliest claimed: 1995-09-21
- Assignees: Dow Corning Corporation; Dow Corning Toray Silicone Co., Ltd.
- Inventors: John Darrell Jones; Michael Ward Skinner; Nobuo Kaiya; Atsushi Togashi; Takateru Yamada
- Web page: https://patentgrep.com/patent/US5708046A

## CPC

- C08K 5/05: Alcohols; Metal alcoholates
- C08K 5/0008: {Organic ingredients according to more than one of the "one dot" groups of C08K5/01 - C08K5/59}
- C09D 183/04: Polysiloxanes
- Y10T 428/31663: As siloxane, silicone or silane
- C08K: Use of inorganic or non-macromolecular organic substances as compounding ingredients (paints, inks, varnishes, dyes, polishes, adhesives C09)
- 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)
- Y10T: TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION

## Abstract

The present invention relates to a curable silicone release coating composition comprising a mixture of an organopolysiloxane containing at least two alkenyl groups per compound, an organohydrogensilicon compound, inhibitors having a boiling point of up to 130.degree. C. at atmospheric pressure, inhibitors having a boiling point of at least 170.degree. C. at atmospheric pressure a platinum group metal-containing catalyst, and optionally a diluent. The silicone release coating compositions are stable when stored at room temperature, especially when the composition is used on a coating roll for the production of a thin films. The compositions of this invention also quickly form a cured film having good release properties for adhesive materials at a comparatively low temperatures.

## Claims

### Claim 1

A curable silicone release coating composition comprising a mixture of:
(A) an organopolysiloxane containing at least two alkenyl groups per compound;
(B) an organohydrogensilicon compound;
(C) an inhibitor having a boiling point of up to 130.degree. C. at atmospheric pressure selected from the group consisting of acetylenic alcohols and silylated acetylenic alcohols;
(D) an inhibitor having a boiling point of at least 170.degree. C. at atmospheric pressure selected from the group consisting of vinylcyclosiloxanes, acetylenic alcohols, and silylated acetylenic alcohols;
(E) a platinum group metal-containing catalyst; and optionally (F) a diluent.

### Claim 2 (depends on 1)

A composition according to claim 1, wherein (A) is an organopolysiloxane compound having its formula selected from the group consisting of
R.sup.1.sub.3 SiO(R.sub.2 SiO).sub.x (RR.sup.1 SiO).sub.y SiR.sup.1.sub.3, (i)
R.sup.1.sub.3 SiO(R.sub.2 SiO).sub.x SiR.sup.1.sub.3, (ii)
and
R.sup.1.sub.3 SiO(RR.sup.1 SiO).sub.y SiR.sup.1.sub.3 (iii)
wherein R is independently selected from monovalent hydrocarbon or halohydrocarbon radicals free of aliphatic unsaturation and having from 1 to 20 carbon atoms, R.sup.1 is independently selected from the group consisting of R and an alkenyl group, x has a value of from greater than zero to 7000, and y has a value of from greater than zero to 350 with the proviso that there are at least two alkenyl groups per compound.

### Claim 3 (depends on 2)

A composition according to claim 2, wherein R.sup.1 is a group having the formula --(CH.sub.2).sub.m CH.dbd.CH.sub.2 or --(CH.sub.2).sub.n CH.dbd.CH--(CH.sub.2).sub.p CH.dbd.CH.sub.2 wherein m has a value of 0 to 20, n has the value of 0 to 9, and p has the value of 3, 4, or 5.

### Claim 4 (depends on 2)

A composition according to claim 2, wherein (A) is an organopolysiloxane compound having its formula selected from the group consisting of ViMe.sub.2 SiO(Me.sub.2 SiO).sub.x SiMe.sub.2 Vi, Me.sub.3 SiO(Me.sub.2 SiO).sub.x (MeViSiO).sub.y SiMe.sub.3, Me.sub.3 SiO(MeViSiO).sub.y SiMe.sub.3, ViMe.sub.2 SiO(Me.sub.2 SiO).sub.x (MeViSiO).sub.y SiMe.sub.2 Vi, ViMe.sub.2 SiO(MeViSiO).sub.y SiMe.sub.2 Vi HexMe.sub.2 SiO(Me.sub.2 SiO).sub.x SiMe.sub.2 Hex, Me.sub.3 SiO(Me.sub.2 SiO).sub.x (MeHexSiO).sub.y SiMe.sub.3, Me.sub.3 SiO(MeHexSiO).sub.y SiMe.sub.3, HexMe.sub.2 SiO(Me.sub.2 SiO).sub.x (MeHexSiO).sub.y SiMe.sub.2 Hex, and HexMe.sub.2 SiO(MeHexSiO).sub.y SiMe.sub.2 Hex wherein Me, Vi, and Hex denote methyl, vinyl, and 5-hexenyl, respectively, x has a value of from greater than zero to 7000, and y has a value of from greater than zero to 350.

### Claim 5 (depends on 1)

A composition according to claim 1, wherein (B) is a compound having its formula selected from the group consisting of HMe.sub.2 SiO(Me.sub.2 SiO).sub.a (MeHSiO).sub.b SiMe.sub.2 H, HMe.sub.2 SiO(Me.sub.2 SiO).sub.a SiMe.sub.2 H, Me.sub.3 SiO(Me.sub.2 SiO).sub.a (MeHSiO).sub.b SiMe.sub.3, HMe.sub.2 SiO(MeHSiO).sub.b SiMe.sub.2 H, and Me.sub.3 SiO(MeHSiO).sub.b SiMe.sub.3 wherein Me denotes methyl wherein a has a value of from greater than zero to 1000 and b has a value of from greater than zero to 200.

### Claim 6 (depends on 1)

A composition according to claim 1, wherein (C) is selected from the group consisting of 1-butyn-3-ol, 1-propyn-3-ol, 3-methyl-1-butyn-3-ol, 3-methyl-1-pentyn-3-ol, and trimethyl(3-methyl-1-butyn-3-oxy)silane.

### Claim 7 (depends on 1)

A composition according to claim 1, wherein (D) is selected from the group consisting of a vinylcyclosiloxane having the average formula (R.sup.2 CH.sub.2 .dbd.CHSiO).sub.m wherein each m has an integer value of 3 to 9 and R.sup.2 denotes methyl, ethyl, or phenyl, 3-phenyl-1-butyn-3-ol, 4-ethyl-1-octyn-3-ol, 1-ethynyl-1-cyclohexanol, methyltris(3-methyl-1-butyn-3-oxy) silane, dimethyl bis(3-methyl-1-butyn-3-oxy)silane, methylvinylbis(3-methyl-1-butyn-3-oxy)silane, diphenylmethyl(3-methyl-1-butyn-3-oxy)silane, dimethylphenyl(3-methyl-1-butyn-3-oxy)silane, dimethylhexenyl(3-methyl-1-butyn-3-oxy)silane, triethyl(3-methyl-1-butyn-3-oxy)silane, methyltrifluoropropyl bis(3-methyl-1-butyn-3-oxy)silane, trimethyl(3,5-dimethyl-1-hexyn-3-oxy)silane, diphenylmethyl(3-phenyl-1-butyn-3-oxy)silane, dimethylphenyl(3-phenyl-1-butyn-3-oxy)silane, dimethylvinyl(3-phenyl-1-butyn-3-oxy)silane, dimethylhexenyl(3-phenyl-1-butyn-3-oxy)silane, dimethylhexenyl(cyclohexyl-1-ethyn-1-oxy)silane, dimethylvinyl(cyclohexyl-1-ethyn-1-oxy)silane, diphenylmethyl(cyclohexyl-1-ethyn-1-oxy)silane, and trimethyl(cyclohexyl-1-ethyn-1-oxy)silane.

### Claim 8 (depends on 1)

A composition according to claim 1, wherein (E) is selected from the group consisting of chloroplatinic acid and chloroplatinic acid-divinyltetramethyldisiloxane complexes.

### Claim 9 (depends on 1)

A composition according to claim 1, wherein (F) is selected from the group consisting of pentane, hexane, heptane, octane, nonane, benzene, toluene, xylene, acetone, methylethyl ketone, methylisobutyl ketone, trichloroethane, perchloroethylene, and bromobenzene.

### Claim 10

A curable silicone release coating composition obtained by a method comprising homogeneously mixing:
(A) an organopolysiloxane containing at least two alkenyl groups per compound;
(B) an organohydrogensilicon compound;
(C) an inhibitor having a boiling point of up to 130.degree. C. at atmospheric pressure selected from the group consisting of acetylenic alcohols and silylated acetylenic alcohols;
(D) an inhibitor having a boiling point of at least 170.degree. C. at atmospheric pressure selected from the group consisting of vinylcyclosiloxanes, acetylenic alcohols, and silylated acetylenic alcohols;
(E) a platinum group metal-containing catalyst; and optionally (F) a diluent.

### Claim 11

A method of making a coated article, the method comprising:
(I) applying a curable silicone coating composition on the surface of a substrate wherein the coating composition is prepared by homogeneously mixing:
(A) an organopolysiloxane containing at least two alkenyl groups per compound;
(B) an organohydrogensilicon compound;
(C) an inhibitor having a boiling point of up to 130.degree. C. at atmospheric pressure selected from the group consisting of acetylenic alcohols and silylated acetylenic alcohols;
(D) an inhibitor having a boiling point of at least 170.degree. C. at atmospheric pressure selected from the group consisting of vinylcyclosiloxanes, acetylenic alcohols, and silylated acetylenic alcohols;
(E) a platinum group metal-containing catalyst; and optionally (F) a diluent; and
(II) exposing the coating and the substrate to an energy source selected from the group consisting of (i) heat and (ii) actinic radiation in an amount sufficient to cure the coating.

### Claim 12 (depends on 11)

A coated article according to claim 11, wherein the method further comprises applying a pressure sensitive adhesive on the coated substrate after step (II).

### Claim 13 (depends on 11)

A coated article produced in accordance with the method of claim 11.

### Claim 14 (depends on 12)

A coated article produced in accordance with the method of claim 12.

### Claim 15

A curable silicone release coating composition comprising a mixture of:
(A') an organopolysiloxane containing at least two alkenyl groups per compound;
(B') an organohydrogensilicon compound;
(C') a conjugated ene-yne inhibitor having a boiling point of up to 130.degree. C. at atmospheric pressure;
(D') an inhibitor having a boiling point of at least 170.degree. C. at atmospheric pressure selected from the group consisting of acetylenic alcohols and silylated acetylenic alcohols;
(E') a platinum group metal-containing catalyst; and optionally (F') a diluent.

### Claim 16 (depends on 15)

A composition according to claim 15, wherein (A') is an organopolysiloxane compound having its formula selected from the group consisting of
R.sup.1.sub.3 SiO(R.sub.2 SiO).sub.x (RR.sup.1 SiO).sub.y SiR.sup.1.sub.3,(i)
R.sup.1.sub.3 SiO(R.sub.2 SiO).sub.x SiR.sup.1.sub.3, (ii)
and
R.sup.1.sub.3 SiO(RR.sup.1 SiO).sub.y SiR.sup.1.sub.3 (iii)
wherein R is independently selected from monovalent hydrocarbon or halohydrocarbon radicals free of aliphatic unsaturation and having from 1 to 20 carbon atoms, R.sup.1 is independently selected from the group consisting of R and an alkenyl group, x has a value of from greater than zero to 7000, and y has a value of from greater than zero to 350 with the proviso that there are at least two alkenyl groups per compound.

### Claim 17 (depends on 16)

A composition according to claim 16, wherein R.sup.1 is a group having the formula --(CH.sub.2).sub.m CH.dbd.CH.sub.2 or --(CH.sub.2).sub.n CH.dbd.CH--(CH.sub.2).sub.p CH.dbd.CH.sub.2 wherein m has a value of 0 to 20, n has the value of 0 to 9, and p has the value of 3, 4, or 5.

### Claim 18 (depends on 16)

A composition according to claim 16, wherein (A') is an organopolysiloxane compound having its formula selected from the group consisting of ViMe.sub.2 SiO(Me.sub.2 SiO).sub.x SiMe.sub.2 Vi, Me.sub.3 SiO(Me.sub.2 SiO).sub.x (MeViSiO).sub.y SiMe.sub.3, Me.sub.3 SiO(MeViSiO).sub.y SiMe.sub.3, ViMe.sub.2 SiO(Me.sub.2 SiO).sub.x (MeViSiO).sub.y SiMe.sub.2 Vi, ViMe.sub.2 SiO(MeViSiO).sub.y SiMe.sub.2 Vi HexMe.sub.2 SiO(Me.sub.2 SiO).sub.x SiMe.sub.2 Hex, Me.sub.3 SiO(Me.sub.2 SiO).sub.x (MeHexSiO).sub.y SiMe.sub.3, Me.sub.3 SiO(MeHexSiO).sub.y SiMe.sub.3, HexMe.sub.2 SiO(Me.sub.2 SiO).sub.x (MeHexSiO).sub.y SiMe.sub.2 Hex, and HexMe.sub.2 SiO(MeHexSiO).sub.y SiMe.sub.2 Hex wherein Me, Vi, and Hex denote methyl, vinyl, and 5-hexenyl, respectively, x has a value of from greater than zero to 7000, and y has a value of from greater than zero to 350.

### Claim 19 (depends on 15)

A composition according to claim 15, wherein (B') is a compound having its formula selected from the group consisting of HMe.sub.2 SiO(Me.sub.2 SiO).sub.a (MeHSiO).sub.b SiMe.sub.2 H, HMe.sub.2 SiO(Me.sub.2 SiO).sub.a SiMe.sub.2 H, Me.sub.3 SiO(Me.sub.2 SiO).sub.a (MeHSiO).sub.b SiMe.sub.3, HMe.sub.2 SiO(MeHSiO).sub.b SiMe.sub.2 H, and Me.sub.3 SiO(MeHSiO).sub.b SiMe.sub.3 wherein Me denotes methyl wherein a has a value of from greater than zero to 1000 and b has a value of from greater than zero to 200.

### Claim 20 (depends on 15)

A composition according to claim 15, wherein (C') is selected from the group consisting of 3,5-dimethyl-3-hexene-1-yne, 3-methyl-3-pentene-1-yne, and 3-methyl-3-hexene-1-yne.

### Claim 21 (depends on 15)

A composition according to claim 15, wherein (D') is selected from the group consisting of 3-phenyl-1-butyn-3-ol, 4-ethyl-1-octyn-3-ol, 1-ethynyl-1-cyclohexanol, methyltris(3-methyl-1-butyn-3-oxy) silane, dimethyl bis(3-methyl-1-butyn-3-oxy)silane, methylvinylbis(3-methyl-1-butyn-3-oxy)silane, diphenylmethyl(3-methyl-1-butyn-3-oxy)silane, dimethylphenyl(3-methyl-1-butyn-3-oxy)silane, dimethylhexenyl(3-methyl-1-butyn-3-oxy)silane, triethyl(3-methyl-1-butyn-3-oxy)silane, methyltrifluoropropyl bis(3-methyl-1-butyn-3-oxy)silane, trimethyl(3,5-dimethyl-1-hexyn-3-oxy)silane, diphenylmethyl(3-phenyl-1-butyn-3-oxy)silane, dimethylphenyl(3-phenyl-1-butyn-3-oxy)silane, dimethylvinyl(3-phenyl-1-butyn-3-oxy)silane, dimethylhexenyl(3-phenyl-1-butyn-3-oxy)silane, dimethylhexenyl(cyclohexyl-1-ethyn-1-oxy)silane, dimethylvinyl(cyclohexyl-1-ethyn-1-oxy)silane, diphenylmethyl(cyclohexyl-1-ethyn-1-oxy)silane, and trimethyl(cyclohexyl-1-ethyn-1-oxy)silane.

### Claim 22 (depends on 15)

A composition according to claim 15, wherein (E') is selected from the group consisting of chloroplatinic acid and chloroplatinic acid-divinyltetramethyldisiloxane complexes.

### Claim 23 (depends on 15)

A composition according to claim 15, wherein (F') is selected from the group consisting of pentane, hexane, heptane, octane, nonane, benzene, toluene, xylene, acetone, methylethyl ketone, methylisobutyl ketone, trichloroethane, perchloroethylene, and bromobenzene.

### Claim 24

A curable silicone release coating composition obtained by a method comprising homogeneously mixing:
(A') an organopolysiloxane containing at least two alkenyl groups per compound;
(B') an organohydrogensilicon compound;
(C') a conjugated ene-yne inhibitor having a boiling point of up to 130.degree. C. at atmospheric pressure;
(D') an inhibitor having a boiling point of at least 170.degree. C. at atmospheric pressure selected from the group consisting of acetylenic alcohols and silylated acetylenic alcohols;
(E') a platinum group metal-containing catalyst; and optionally (F') a diluent.

### Claim 25

A method of making a coated article, the method comprising:
(I) applying a curable silicone coating composition on the surface of a substrate wherein the coating composition is prepared by homogeneously mixing:
(A') an organopolysiloxane containing at least two alkenyl groups per compound;
(B') an organohydrogensilicon compound;
(C') a conjugated ene-yne inhibitor having a boiling point of up to 130.degree. C. at atmospheric pressure;
(D') an inhibitor having a boiling point of at least 170.degree. C. at atmospheric pressure selected from the group consisting of acetylenic alcohols and silylated acetylenic alcohols;
(E') a platinum group metal-containing catalyst; and optionally (F') a diluent; and
(II) exposing the coating and the substrate to an energy source selected from the group consisting of (i) heat and (ii) actinic radiation in an amount sufficient to cure the coating.

### Claim 26 (depends on 25)

A coated article according to claim 25, wherein the method further comprises applying a pressure sensitive adhesive on the coated substrate after step (II).

### Claim 27 (depends on 25)

A coated article produced in accordance with the method of claim 25.

### Claim 28 (depends on 26)

A coated article produced in accordance with the method of claim 26.