# US 5,708,075 A · Silicone release coating compositions > Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt - Number: US 5,708,075 A - Document ID: US5708075A - Status: Granted - Kind: A - Application number: 08/775,037 - Filed: 1996-12-30 - Granted: 1998-01-13 - Earliest claimed: 1996-12-30 - Assignees: Dow Corning Corporation - Inventors: Kyuha Chung; Robert Alan Ekeland; Randall Gene Schmidt - Web page: https://patentgrep.com/patent/US5708075A ## CPC - C09D 183/04: Polysiloxanes - Y10T 428/31663: As siloxane, silicone or silane - 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) an organopolysiloxane having at least two alkenyl groups per molecule, (B) an organohydrogensiloxane having at least two silicon-bonded hydrogen atoms per molecule, (C) a siloxane resin having silicon-bonded hydrogen groups, (D) a platinum group metal-containing catalyst, and optionally (E) an inhibitor. The compositions of this invention are useful as release coatings for pressure sensitive adhesives. ## Claims ### Claim 1 A curable silicone release coating composition comprising: (A) an organopolysiloxane having at least two alkenyl groups per molecule; (B) a linear organohydrogenpolysiloxane having at least two silicon-bonded hydrogen atoms per molecule; (C) a siloxane resin having the formula (R.sub.3 SiO.sub.1/2).sub.a (HR.sub.2 SiO.sub.1/2).sub.b (SiO.sub.4/2).sub.c wherein R is a monovalent hydrocarbon group having from 1 to 10 carbon atoms, a has a value of 1 to 25, b has a value of 2 to 10, c has a value of 1 to 50, and having a molar ratio of M units to Q units of from 0.6/1 to 4/1 wherein M denotes the monovalent (R.sub.3 SiO.sub.1/2).sub.2 units and the monovalent (HR.sub.2 SiO.sub.1/2).sub.b units and Q denotes the tetravalent (SiO.sub.4/2).sub.c units; and (D) a platinum group metal-containing catalyst. ### Claim 2 (depends on 1) A composition according to claim 1, wherein (A) is an organopolysiloxane 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 3 (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.f (MeHSiO).sub.g SiMe.sub.2 H, HMe.sub.2 SiO(Me.sub.2 SiO).sub.f SiMe.sub.2 H, Me.sub.3 SiO(Me.sub.2 SiO).sub.f (MeHSiO).sub.g SiMe.sub.3, HMe.sub.2 SiO(MeHSiO).sub.g SiMe.sub.2 H, and Me.sub.3 SiO(MeHSiO).sub.g SiMe.sub.3 wherein Me denotes methyl wherein f has a value of from greater than zero to 1000 and g has a value of from greater than zero to 200. ### Claim 4 (depends on 1) A composition according to claim 1, wherein b has a value of 3 to 5. ### Claim 5 (depends on 1) A composition according to claim 1, wherein (C) has a molar ratio of M units to Q units of from 1/1 to 2/1. ### Claim 6 (depends on 1) A composition according to claim 1, wherein (D) is selected from the group consisting of chloroplatinic acid, alcohol modified chloroplatinic acids, olefin complexes of chloroplatinic acid, complexes of chloroplatinic acid and divinyltetramethyldisiloxane, fine platinum particles adsorbed on carbon carriers, and platinum black. ### Claim 7 (depends on 1) A composition according to claim 1, wherein the composition further comprises (E) an inhibitor. ### Claim 8 (depends on 7) A composition according to claim 7, wherein (E) is selected from the group consisting of maleates, fumarates, acetylenic alcohols, silylated acetylenic alcohols, conjugated ene-ynes, and cyclic siloxanes. ### Claim 9 (depends on 1) A composition according to claim 1, wherein the composition further comprises at least one ingredient selected from the group consisting of a siloxane resin consisting essentially of at least one R.sup.3.sub.3 SiO.sub.1/2 (M) unit and at least one SiO.sub.4/2 (Q) unit wherein R.sup.3 is independently selected from the group consisting of a monovalent hydrocarbon group having from 1 to 10 carbon atoms and an alkenyl group having from 2 to 10 carbon atoms, and having a molar ratio of M units to Q units ranges from 0.4/1 to 4/1, a bath life extender, and a diluent. ### Claim 10 (depends on 9) A composition according to claim 9, wherein the siloxane resin is selected from the group consisting of a siloxane resin consisting essentially of: Me.sub.3 SiO.sub.1/2 (M) and SiO.sub.4/2 (Q) units, a siloxane resin consisting essentially of: Me.sub.2 ViSiO.sub.1/2 (M) and SiO.sub.4/2 (Q) units, and a siloxane resin consisting essentially of: Me.sub.3 SiO.sub.1/2 (M), Me.sub.2 ViSiO.sub.1/2 (M), and SiO.sub.4/2 (Q) units, wherein Me denotes methyl, Vi denotes vinyl, and the molar ratio of M to Q units is from 0.6/1 to 1.9/1. ### Claim 11 (depends on 9) A composition according to claim 9, wherein the bath life extender is selected from the group consisting of compounds which contain one or more primary or secondary alcohol groups, carboxylic acids, compounds which yield carboxylic acids when exposed to water at room temperature, cyclic ethers, and water. ### Claim 12 (depends on 9) A composition according to claim 9, wherein the diluent is selected from the group consisting of pentane, hexane, heptane, octane, nonane, benzene, toluene, xylene, acetone, methylethyl ketone, and methylisobutyl ketone, trichloroethane, perchloroethylene, and bromobenzene. ### Claim 13 A curable silicone release coating composition obtained by a method comprising (I) mixing: (A) an organopolysiloxane having at least two alkenyl groups per molecule; (B) a linear organohydrogenpolysiloxane having at least two silicon-bonded hydrogen atoms per molecule; (C) a siloxane resin having the formula (R.sub.3 SiO.sub.1/2).sub.a (HR.sub.2 SiO.sub.1/2).sub.b (SiO.sub.4/2).sub.c wherein R is a monovalent hydrocarbon group having from 1 to 10 carbon atoms, a has a value of 1 to 25, b has a value of 2 to 10, c has a value of 1 to 50, and having a molar ratio of M units to Q units of from 0.6/1 to 4/1 wherein M denotes the monovalent (R.sub.3 SiO.sub.1/2).sub.a units and the monovalent (HR.sub.2 SiO.sub.1/2).sub.b units and Q denotes the tetravalent (SiO.sub.4/2).sub.c units; and (D) a platinum group metal-containing catalyst. ### Claim 14 (depends on 13) A composition according to claim 13, wherein (A) is an organopolysiloxane 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 0 to 7000, and y has a value of from greater than 0 to 350. ### Claim 15 (depends on 13) A composition according to claim 13, wherein (B) is a compound having its formula selected from the group consisting of HMe.sub.2 SiO(Me.sub.2 SiO).sub.d (MeHSiO).sub.e SiMe.sub.2 H, HMe.sub.2 SiO(Me.sub.2 SiO).sub.d SiMe.sub.2 H, Me.sub.3 SiO(Me.sub.2 SiO).sub.d (MeHSiO).sub.e SiMe.sub.3, HMe.sub.2 SiO(MeHSiO).sub.e SiMe.sub.2 H, and Me.sub.3 SiO(MeHSiO).sub.e SiMe.sub.3 wherein Me denotes methyl wherein d has a value of from greater than zero to 1000 and e has a value of from greater than zero to 200. ### Claim 16 (depends on 13) A composition according to claim 13, wherein b has a value of 3 to 5. ### Claim 17 (depends on 13) A composition according to claim 13, wherein (C) has a molar ratio of M units to Q units of from 1/1 to 2/1. ### Claim 18 (depends on 13) A composition according to claim 13, wherein (D) is selected from the group consisting of chloroplatinic acid, alcohol modified chloroplatinic acids, olefin complexes of chloroplatinic acid, complexes of chloroplatinic acid and divinyltetramethyldisiloxane, fine platinum particles adsorbed on carbon carriers, and platinum black. ### Claim 19 (depends on 13) A composition according to claim 13, wherein the method further comprises adding, during step (I), (E) an inhibitor. ### Claim 20 (depends on 19) A composition according to claim 19, wherein (E) is selected from the group consisting of maleates, fumarates, acetylenic alcohols, silylated acetylenic alcohols, conjugated ene-ynes, and cyclic siloxanes. ### Claim 21 (depends on 13) A composition according to claim 13, wherein the method further comprises adding, during step (I), at least one ingredient selected from the group consisting of a siloxane resin consisting essentially of at least one R.sup.3.sub.3 SiO.sub.1/2 (M) unit and at least one SiO.sub.4/2 (Q) unit wherein R.sup.3 is independently selected from the group consisting of hydrogen, a monovalent hydrocarbon group having from 1 to 10 carbon atoms, and an alkenyl group having from 2 to 10 carbon atoms, and having a molar ratio of M Units to Q units ranges from 0.4/1 to 4/1, a bath life extender, and a diluent. ### Claim 22 (depends on 21) A composition according to claim 21, wherein the siloxane resin is selected from the group consisting of a siloxane resin consisting essentially of: Me.sub.3 SiO.sub.1/2 (M) and SiO.sub.4/2 (Q) units, a siloxane resin consisting essentially of: Me.sub.2 ViSiO.sub.1/2 (M) and SiO.sub.4/2 (Q) units, and a siloxane resin consisting essentially of: Me.sub.3 SiO.sub.1/2 (M), Me.sub.2 ViSiO.sub.1/2 (M), and SiO.sub.4/2 (Q) units, wherein Me denotes methyl, Vi denotes vinyl, and the molar ratio of M to Q units is from 0.6/1 to 1.9/1. ### Claim 23 (depends on 21) A composition according to claim 21, wherein the bath life extender is selected from the group consisting of compounds which contain one or more primary or secondary alcohol groups, carboxylic acids, compounds which yield carboxylic acids when exposed to water at room temperature, cyclic ethers, and water. ### Claim 24 (depends on 21) A composition according to claim 21, wherein the diluent is selected from the group consisting of pentane, hexane, heptane, octane, nonane, benzene, toluene, xylene, acetone, methylethyl ketone, and methylisobutyl ketone, trichloroethane, perchloroethylene, and bromobenzene. ### Claim 25 A coated substrate obtained by a method comprising (I) applying a curable silicone composition on the surface of a substrate wherein the curable silicone composition is obtained by mixing: (A) an organopolysiloxane having at least two alkenyl groups per molecule; (B) a linear organohydrogenpolysiloxane having at least two silicon-bonded hydrogen atoms per molecule; (C) a siloxane resin having the formula (R.sub.3 SiO.sub.1/2).sub.a (HR.sub.2 SiO.sub.1/2).sub.b (SiO.sub.4/2).sub.c wherein R is a monovalent hydrocarbon group having from 1 to 10 carbon atoms, a has a value of 1 to 25, b has a value of 2 to 10, c has a value of 1 to 50, and having a molar ratio of M units to Q units of from 0.6/1 to 4/1 wherein M denotes the monovalent (R.sub.3 SiO.sub.1/2).sub.a units and the monovalent (HR.sub.2 SiO.sub.1/2).sub.b units and Q denotes the tetravalent (SiO.sub.4/2).sub.c units; and (D) a platinum group metal-containing catalyst. ### Claim 26 (depends on 25) A coated substrate according to claim 25, wherein the method further comprises (II) exposing the coating and the substrate to heat in an amount sufficient to cure the coating. ### Claim 27 (depends on 26) A coated article according to claim 26, wherein the method further comprises applying a pressure sensitive adhesive on the coated substrate after step (II).