Patent US5486578A successfully refreshed from Google Patents.
← Back to Patent Explorer
US5486578A Expired / Lapsed US ⏱️ 0.0 years remaining

Curable silicone coatings containing silicone resins

Assignee: Dow Silicones Corp
•
Filing: 1994-12-20
•
Granted: 1996-01-23
•
Expires: 2014-12-20
📄 Original PDF 🌐 Google Patents 🔄 Sync Now

Abstract

Abstract The present invention relates to curable silicone coatings containing silicone resins. More particularly the present invention relates to curable silicone coating compositions comprising an olefinic organopolysiloxane, an organohydrogensiloxane, a platinum catalyst, and silicone resins in which the resins are prepared by a continuous method whereby the ratio of reactants is kept constant thus producing less variation in the final silicone resin that is produced. The silicone resins provide beneficial release properties when added to curable silicone coating compositions.

Inventors

  • 👤 II Leslie E. Carpenter
  • 👤 Robert A. Ekeland

Bibliographic Details

Application Number —
Jurisdiction US
Data Source google_patents
Last Synchronized 2026-11-05 11:02
CPC Classifications
C; C09; C09D; C09D183/00; C09D183/04; C08; C08G; C08G77/00; C08G77/04; C08G77/06

Claims Analysis

Total Claims: 39
Claim 1
Independent Claim 228 words
A curable silicone coating composition comprising: (A) an organosilicon compound having at least two olefinic hydrocarbon radicals per compound; (B) at least one organohydrogensilicon compound; (C) a platinum group metal-containing catalyst; and (D) a silicone resin prepared by the process of: (I) mixing in a continuous manner a silane selected from the group consisting of: (a) a silane having the formula SiX 4 wherein X is a halogen atom or a group having the formula OR wherein R is a group selected from the group consisting of alkyl groups having from 1 to 6 carbon atoms, aryl groups, and arylalkyl groups; (b) alcohol treated halogenated silanes; and (c) alkyl silicates having units of the formula ##STR4## or a partial hydrolysis condensate thereof, wherein R 1 is a group selected from the group consisting of alkyl groups having from 1 to 6 carbon atoms, aryl groups, and arylalkyl groups, and d has a value of from 1 to 3, with a condensation catalyst; (II) adding a quenching agent to the reaction mixture of (I), whereby an aqueous layer or condensation catalyst layer and an organic-silicone resin containing layer are formed; (III) separating the aqueous layer or condensation catalyst layer from the organic-silicone resin containing layer; and (IV) stripping the organic-silicone resin containing layer, wherein the weight ratio of said silane to said condensation catalyst is constant throughout said process.
Claim 2
Dependent Claim 228 words
A curable silicone coating composition comprising: (A) an organosilicon compound having at least two olefinic hydrocarbon radicals per compound; (B) at least one organohydrogensilicon compound; (C) a platinum group metal-containing catalyst; and (D) a silicone resin prepared by the process of: (I) mixing in a continuous manner a silane selected from the group consisting of: (a) a silane having the formula SiX 4 wherein X is a halogen atom or a group having the formula OR wherein R is a group selected from the group consisting of alkyl groups having from 1 to 6 carbon atoms, aryl groups, and arylalkyl groups; (b) alcohol treated halogenated silanes; and (c) alkyl silicates having units of the formula ##STR4## or a partial hydrolysis condensate thereof, wherein R 1 is a group selected from the group consisting of alkyl groups having from 1 to 6 carbon atoms, aryl groups, and arylalkyl groups, and d has a value of from 1 to 3, with a condensation catalyst; (II) adding a quenching agent to the reaction mixture of (I), whereby an aqueous layer or condensation catalyst layer and an organic-silicone resin containing layer are formed; (III) separating the aqueous layer or condensation catalyst layer from the organic-silicone resin containing layer; and (IV) stripping the organic-silicone resin containing layer, wherein the weight ratio of said silane to said condensation catalyst is constant throughout said process.
Claim 3
Dependent Claim 174 words
A composition according to claim 1, wherein (A) is selected from the group consisting of ViMe 2 SiO(Me 2 SiO) a SiMe 2 Vi, HexMe 2 SiO(Me 2 SiO) a SiMe 2 Hex, Vi 2 MeSiO(Me 2 SiO) a SiMeVi 2 , Hex 2 MeSiO(Me 2 SiO) a SiMeHex 2 , Vi 3 SiO(Me 2 SiO) a SiVi 3 , Hex 3 SiO(Me 2 SiO) a SiHex 3 , PhMeViSiO(Me 2 SiO) a SiPhMeVi, HexMe 2 SiO(Me 2 SiO) a (MeHexSiO) b SiMe 2 Hex, ViMe 2 SiO(Me 2 SiO) a (MeViSiO) b SiMe 2 Vi, Hex 2 MeSiO(Me 2 SiO) a (MeHexSiO) b SiMeHex 2 , Vi 2 MeSiO(Me 2 SiO) a (MeViSiO) b SiMeVi 2 , Hex 3 SiO(Me 2 SiO) a (MeHexSiO) b SiHex 3 , and Vi 3 SiO(Me 2 SiO) a (MeViSiO) b SiVi 3 , wherein Me, Vi, Hex, and Ph denote methyl, vinyl, 5-hexenyl and phenyl, respectively and a has a value of from 0 to 1000, and b has a value of from 0 to 100.
Claim 4
Dependent Claim 27 words
A composition according to claim 21, wherein (B) is selected from the group consisting of bis(trimethylsiloxy)dimethyldihydrogendisiloxane, heptamethylhydrogentrisiloxane, hexamethyldihydrogentrisiloxane, methylhydrogencyclosiloxanes, pentamethylpentahydrogencyclopentasiloxane, pentamethylhydrogendisiloxane, polymethylhydrogensiloxanes, tetramethyltetrahydrogencyclotetrasiloxane, tetramethyldihydrogendisiloxane, and methylhydrogendimethylsiloxane copolymers.
Claim 5
Dependent Claim 17 words
A composition according to claim 1, wherein (C) is selected from chloroplatinic acid or chloroplatinic acid-divinyltetramethyldisiloxane complexes.
Claim 6
Dependent Claim 19 words
A composition according to claim 1, wherein (a) is selected from the group consisting of tetramethoxysilane, tetraethoxysilane, and tetrapropoxysilane.
Claim 7
Dependent Claim 28 words
A composition according to claim 1, wherein the halogenated silane of (b) is selected from the group consisting of trimethylchlorosilane, triethylchlorosilane, trimethylbromosilane, triethylbromosilane, trimethylfluorosilane, triethylfluorosilane, dimethylvinylchlorosilane, and dimethyl-5-hexenylchlorosilane.
Claim 8
Dependent Claim 22 words
A composition according to claim 1, wherein the alcohol of (b) is selected from the group consisting of ethanol, methanol, and isopropanol.
Claim 9
Dependent Claim 10 words
A composition according to claim 1, wherein (c) is ethylpolysilicate.
Claim 10
Dependent Claim 24 words
A composition according to claim 1, wherein the condensation catalyst is selected from the group consisting of hydrochloric acid, sulfuric acid, and sulfonic acids.
Claim 11
Dependent Claim 119 words
A composition according to claim 1, wherein the quenching agent is a silane having the formula R 5 R 6 R 7 SiZ wherein R 5 , R 6 and R 7 are selected from hydrogen, alkyl groups having from 1 to 12 carbon atoms, alkenyl groups having from 2 to 12 carbon atoms, aryl groups, arylalkyl groups, or perfluoroalkylethyl groups having the formula C n F 2n+1 CH 2 CH 2 where n is 1 to 6, and Z is a halogen atom or is a group having the formula OR 8 wherein R 8 is a group selected from the group consisting of alkyl groups having from 1 to 6 carbon atoms, aryl groups, and arylalkyl groups.
Claim 12
Dependent Claim 28 words
A composition according to claim 1, wherein the quenching agent is a disiloxane selected from the group consisting of tetramethyldisiloxane, hexamethyldisiloxane, tetramethyldivinylsiloxane, tetramethyldi-5-hexenylsiloxane, tetramethyl-3,3,3-trifluoropropyldisiloxane, tetramethyldiethylsiloxane, tetramethyldiphenyldisiloxane, and diethyldiphenyldivinyldisiloxane.
Claim 13
Dependent Claim 15 words
A composition according to claim 1, wherein the quenching agent further comprises an organic solvent.
Claim 14
Dependent Claim 20 words
A composition according to claim 12, wherein the organic solvent is selected from the group consisting of heptane and xylene.
Claim 15
Dependent Claim 25 words
A composition according to claim 1, wherein the composition further comprises an inhibitor which inhibits the catalytic activity of the platinum group metal containing catalyst.
Claim 16
Dependent Claim 19 words
A composition according to claim 14, wherein the inhibitor is selected from the group consisting of maleates and fumarates.
Claim 17
Dependent Claim 16 words
A composition according to claim 14, wherein the composition further comprises a bath life extender compound.
Claim 18
Dependent Claim 38 words
A composition according to claim 16, wherein the bath life extender compound is a compound selected from the group consisting of compounds which contain one or more primary or secondary alcohol groups, carboxylic acids, cyclic ethers, and water.
Claim 19
Dependent Claim 13 words
A composition according to claim 1, wherein the composition further comprises a diluent.
Claim 20
Dependent Claim 159 words
A curable silicone coating composition comprising: (A) an organosilicon compound having at least two olefinic hydrocarbon radicals per compound; (B) at least one organohydrogensilicon compound; (C) a platinum group metal-containing catalyst; and (D) a silicone resin prepared by the process of: (I) mixing in a continuous manner a silane selected from the group consisting of: (i) alkoxysilanes, (ii) halogenated silanes, and (iii) alkyl silicates with a silicon compound selected from the group consisting of: (iv) trialkylhalosilanes and (v) disiloxanes; (II) adding an alcohol to the mixture of (I); (III) adding water or a mixture of water and a condensation catalyst to the mixture of (II) whereby an aqueous layer and an organic-silicone resin containing layer are formed; (IV) separating the aqueous layer from the organic-silicone resin containing layer; (V) stripping the organic-silicone resin containing layer; wherein the weight ratio of said silane to said water or to said mixture of water and condensation catalyst is constant throughout said process.
Claim 21
Dependent Claim 159 words
A curable silicone coating composition comprising: (A) an organosilicon compound having at least two olefinic hydrocarbon radicals per compound; (B) at least one organohydrogensilicon compound; (C) a platinum group metal-containing catalyst; and (D) a silicone resin prepared by the process of: (I) mixing in a continuous manner a silane selected from the group consisting of: (i) alkoxysilanes, (ii) halogenated silanes, and (iii) alkyl silicates with a silicon compound selected from the group consisting of: (iv) trialkylhalosilanes and (v) disiloxanes; (II) adding an alcohol to the mixture of (I); (III) adding water or a mixture of water and a condensation catalyst to the mixture of (II) whereby an aqueous layer and an organic-silicone resin containing layer are formed; (IV) separating the aqueous layer from the organic-silicone resin containing layer; (V) stripping the organic-silicone resin containing layer; wherein the weight ratio of said silane to said water or to said mixture of water and condensation catalyst is constant throughout said process.
Claim 22
Dependent Claim 174 words
A composition according to claim 19, wherein (A) is selected from the group consisting of ViMe 2 SiO(Me 2 SiO) a SiMe 2 Vi, HexMe 2 SiO(Me 2 SiO) a SiMe 2 Hex, Vi 2 MeSiO(Me 2 SiO) a SiMeVi 2 , Hex 2 MeSiO(Me 2 SiO) a SiMeHex 2 , Vi 3 SiO(Me 2 SiO) a SiVi 3 , Hex 3 SiO(Me 2 SiO) a SiHex 3 , PhMeViSiO(Me 2 SiO) a SiPhMeVi, HexMe 2 SiO(Me 2 SiO) a (MeHexSiO) b SiMe 2 Hex, ViMe 2 SiO(Me 2 SiO) a (MeViSiO) b SiMe 2 Vi, Hex 2 MeSiO(Me 2 SiO) a (MeHexSiO) b SiMeHex 2 , Vi 2 MeSiO(Me 2 SiO) a (MeViSiO) b SiMeVi 2 , Hex 3 SiO(Me 2 SiO) a (MeHexSiO) b SiHex 3 , and Vi 3 SiO(Me 2 SiO) a (MeViSiO) b SiVi 3 , wherein Me, Vi, Hex, and Ph denote methyl, vinyl, 5-hexenyl and phenyl, respectively and a has a value of from 0 to 1000, and b has a value of from 0 to 100.
Claim 23
Dependent Claim 27 words
A composition according to claim 19, wherein (B) is selected from the group consisting of bis(trimethylsiloxy)dimethyldihydrogendisiloxane, heptamethylhydrogentrisiloxane, hexamethyldihydrogentrisiloxane, methylhydrogencyclosiloxanes, pentamethylpentahydrogencyclopentasiloxane, pentamethylhydrogendisiloxane, polymethylhydrogensiloxanes, tetramethyltetrahydrogencyclotetrasiloxane, tetramethyldihydrogendisiloxane, and methylhydrogendimethylsiloxane copolymers.
Claim 24
Dependent Claim 17 words
A composition according to claim 19, wherein (C) is selected from chloroplatinic acid or chloroplatinic acid-divinyltetramethyldisiloxane complexes.
Claim 25
Dependent Claim 19 words
A composition according to claim 19, wherein (i) is selected from the group consisting of tetramethoxysilane, tetraethoxysilane, and tetrapropoxysilane.
Claim 26
Dependent Claim 10 words
A composition according to claim 19, wherein (ii) is tetrachlorosilane.
Claim 27
Dependent Claim 10 words
A composition according to claim 19, wherein (iii) is ethylpolysilicate.
Claim 28
Dependent Claim 24 words
A composition according to claim 19, wherein (iv) is selected from the group consisting of trimethylchlorosilane, triethylchlorosilane, trimethylbromosilane, triethylbromosilane, trimethylfluorosilane, triethylfluorosilane, dimethylvinylchlorosilane, and dimethyl-5-hexenylchlorosilane.
Claim 29
Dependent Claim 24 words
A composition according to claim 19, wherein (v) is selected from the group consisting of tetramethyldisiloxane, hexamethyldisiloxane, tetramethyldivinylsiloxane, tetramethyldi-5-hexenylsiloxane, tetramethyl-3,3,3-trifluoropropyldisiloxane, tetramethyldiethylsiloxane, tetramethyldiphenyldisiloxane, and diethyldiphenyldivinyldisiloxane.
Claim 30
Dependent Claim 20 words
A composition according to claim 19, wherein the alcohol is selected from the group consisting of ethanol, methanol, and isopropanol.
Claim 31
Dependent Claim 24 words
A composition according to claim 19, wherein the condensation catalyst is selected from the group consisting of hydrochloric acid, sulfuric acid, and sulfonic acids.
Claim 32
Dependent Claim 14 words
A composition according to claim 19, further comprising heating the mixture after step (III).
Claim 33
Dependent Claim 25 words
A composition according to claim 19, wherein the composition further comprises an inhibitor which inhibits the catalytic activity of the platinum group metal containing catalyst.
Claim 34
Dependent Claim 16 words
A composition according to claim 31, wherein the composition further comprises a bath life extender compound.
Claim 35
Dependent Claim 13 words
A composition according to claim 19, wherein the composition further comprises a diluent.
Claim 36
Dependent Claim 306 words
A process for preparing a laminate of a substrate and an adhesive wherein the adhesive will release from the substrate, the process comprising the steps of: (I) coating a curable silicone coating composition on the surface of the substrate wherein the composition comprises: (A) an organosilicon compound having at least two olefinic hydrocarbon radicals per compound; (B) at least one organohydrogensilicon compound; (C) a platinum group metal-containing catalyst; and (D) a silicone resin prepared by the process of: (I) mixing in a continuous manner a silane selected from the group consisting of: (a) a silane having the formula SiX 4 wherein X is a halogen atom or a group having the formula OR wherein R is a group selected from the group consisting of alkyl groups having from 1 to 6 carbon atoms, aryl groups, and arylalkyl groups; (b) alcohol treated halogenated silanes; and (c) alkyl silicates having units of the formula ##STR5## or a partial hydrolysis condensate thereof, wherein R 1 is a group selected from the group consisting of alkyl groups having from 1 to 6 carbon atoms, aryl groups, and arylalkyl groups, and d has a value of from 1 to 3, with a condensation catalyst; (II) adding a quenching agent to the reaction mixture of (I), whereby an aqueous layer or condensation catalyst layer and an organic-silicone resin containing layer are formed; (III) separating the aqueous layer or condensation catalyst layer from the organic-silicone resin containing layer; and (IV) stripping the organic-silicone resin containing layer, wherein the weight ratio of said silane to said condensation catalyst is constant throughout said process; (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; and (III) applying a pressure sensitive adhesive on the coating.
Claim 37
Dependent Claim 306 words
A process for preparing a laminate of a substrate and an adhesive wherein the adhesive will release from the substrate, the process comprising the steps of: (I) coating a curable silicone coating composition on the surface of the substrate wherein the composition comprises: (A) an organosilicon compound having at least two olefinic hydrocarbon radicals per compound; (B) at least one organohydrogensilicon compound; (C) a platinum group metal-containing catalyst; and (D) a silicone resin prepared by the process of: (I) mixing in a continuous manner a silane selected from the group consisting of: (a) a silane having the formula SiX 4 wherein X is a halogen atom or a group having the formula OR wherein R is a group selected from the group consisting of alkyl groups having from 1 to 6 carbon atoms, aryl groups, and arylalkyl groups; (b) alcohol treated halogenated silanes; and (c) alkyl silicates having units of the formula ##STR5## or a partial hydrolysis condensate thereof, wherein R 1 is a group selected from the group consisting of alkyl groups having from 1 to 6 carbon atoms, aryl groups, and arylalkyl groups, and d has a value of from 1 to 3, with a condensation catalyst; (II) adding a quenching agent to the reaction mixture of (I), whereby an aqueous layer or condensation catalyst layer and an organic-silicone resin containing layer are formed; (III) separating the aqueous layer or condensation catalyst layer from the organic-silicone resin containing layer; and (IV) stripping the organic-silicone resin containing layer, wherein the weight ratio of said silane to said condensation catalyst is constant throughout said process; (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; and (III) applying a pressure sensitive adhesive on the coating.
Claim 38
Dependent Claim 237 words
A process for preparing a laminate of a substrate and an adhesive wherein the adhesive will release from the substrate, the process comprising the steps of: (I) coating a curable silicone coating composition on the surface of the substrate wherein the composition comprises: (A) an organosilicon compound having at least two olefinic hydrocarbon radicals per compound; (B) at least one organohydrogensilicon compound; (C) a platinum group metal-containing catalyst; and (D) a silicone resin prepared by the process of: (I) mixing in a continuous manner a silane selected from the group consisting of: (i) alkoxysilanes, (ii) halogenated silanes, and (iii) alkyl silicates with a silicon compound selected from the group consisting of: (iv) trialkylhalosilanes and (v) disiloxanes; (II) adding an alcohol to the mixture of (I); (III) adding water or a mixture of water and a condensation catalyst to the mixture of (II) whereby an aqueous layer and an organic-silicone resin containing layer are formed; (IV) separating the aqueous layer from the organic-silicone resin containing layer; (V) stripping the organic-silicone resin containing layer; wherein the weight ratio of said silane to said water or to said mixture of water and condensation catalyst is constant throughout said process; (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; and (III) applying a pressure sensitive adhesive on the coating.
Claim 39
Dependent Claim 237 words
A process for preparing a laminate of a substrate and an adhesive wherein the adhesive will release from the substrate, the process comprising the steps of: (I) coating a curable silicone coating composition on the surface of the substrate wherein the composition comprises: (A) an organosilicon compound having at least two olefinic hydrocarbon radicals per compound; (B) at least one organohydrogensilicon compound; (C) a platinum group metal-containing catalyst; and (D) a silicone resin prepared by the process of: (I) mixing in a continuous manner a silane selected from the group consisting of: (i) alkoxysilanes, (ii) halogenated silanes, and (iii) alkyl silicates with a silicon compound selected from the group consisting of: (iv) trialkylhalosilanes and (v) disiloxanes; (II) adding an alcohol to the mixture of (I); (III) adding water or a mixture of water and a condensation catalyst to the mixture of (II) whereby an aqueous layer and an organic-silicone resin containing layer are formed; (IV) separating the aqueous layer from the organic-silicone resin containing layer; (V) stripping the organic-silicone resin containing layer; wherein the weight ratio of said silane to said water or to said mixture of water and condensation catalyst is constant throughout said process; (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; and (III) applying a pressure sensitive adhesive on the coating.

USPTO Annuity & Maintenance Windows

Annuity Stage Window Opens Payment Deadline Surcharge Period Until Estimated Fee Status
3.5 Years (Year 4) 1999-01-22 1999-07-24 2000-01-23 $2000.00 Window Closed / Lapsed
7.5 Years (Year 8) 2003-01-22 2003-07-24 2004-01-23 $3760.00 Window Closed / Lapsed
11.5 Years (Year 12) 2007-01-22 2007-07-24 2008-01-23 $7700.00 Window Closed / Lapsed

Assigned Categories & Tags

No categories assigned to this patent yet.

Assign Category Tag