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US4609574A Expired / Lapsed US ⏱️ 0.0 years remaining

Silicone release coatings containing higher alkenyl functional siloxanes

Assignee: Dow Silicones Corp
•
Filing: 1985-10-03
•
Granted: 1986-09-02
•
Expires: 2005-10-03
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Abstract

Abstract An improved, curable, silicone, release coating composition is provided which cures more rapidly, at lower temperature, and with less residual reactive functionality. The composition contains siloxane polymers bearing higher alkenyl groups with 6 or more carbon atoms and cures by the metal catalyzed reaction of SiH with the alkenyl groups. An improved on-line process for preparing release laminates of substrates and adhesive using the coating composition is further provided.

Inventors

  • 👤 John R. Keryk
  • 👤 Peter Y. K. Lo
  • 👤 LeRoy E. Thayer

Bibliographic Details

Application Number —
Jurisdiction US
Data Source google_patents
Last Synchronized 2026-10-28 10:23
CPC Classifications
C; C08; C08G; C08G77/00; C08G77/04; C08G77/20; C08L; C08L83/00; C08L83/04; C08G77/12; Y; Y10; Y10T; Y10T428/00; Y10T428/31504; Y10T428/31652; Y10T428/31663

Claims Analysis

Total Claims: 33
Claim 1
Independent Claim 197 words
A curable coating composition comprising: (A) a triorganosiloxane-endblocked polydiorganosiloxane polymer having a viscosity at 25° C. of at least 25 centistokes, wherein 90 to 99.5 percent of all organic radicals are methyl, from 0.5 to 10 percent of all organic radicals are unsaturated radicals independently selected from the group consisting of the vinyl radical and higher alkenyl radicals represented by the formula --R(CH 2 ) m CH═CH 2 wherein R denotes --(CH 2 ) n -- or --(CH 2 ) p CH═CH-- and m has the value of 1, 2, or 3; n has the value of 3 or 6; and p has the value of 3, 4, or 5, with the proviso that at least 50 mole percent of the unsaturated radicals are higher alkenyl radicals; (B) a catalytic amount of a metal, hydrosilylation catalyst; (C) a methylhydrogenpolysiloxane cross-linking agent, compatible with (A) and having an average of at least three silicon-bonded hydrogen atoms per molecule with the hydrogen radicals being bonded to separate silicon atoms; (D) an effective amount of an inhibitor for the metal, hydrosilylation catalyst; and wherein the composition contains 0.8 to 1.5 silicon-bonded hydrogen radicals for every unsaturated radical in the composition.
Claim 2
Dependent Claim 197 words
A curable coating composition comprising: (A) a triorganosiloxane-endblocked polydiorganosiloxane polymer having a viscosity at 25° C. of at least 25 centistokes, wherein 90 to 99.5 percent of all organic radicals are methyl, from 0.5 to 10 percent of all organic radicals are unsaturated radicals independently selected from the group consisting of the vinyl radical and higher alkenyl radicals represented by the formula --R(CH 2 ) m CH═CH 2 wherein R denotes --(CH 2 ) n -- or --(CH 2 ) p CH═CH-- and m has the value of 1, 2, or 3; n has the value of 3 or 6; and p has the value of 3, 4, or 5, with the proviso that at least 50 mole percent of the unsaturated radicals are higher alkenyl radicals; (B) a catalytic amount of a metal, hydrosilylation catalyst; (C) a methylhydrogenpolysiloxane cross-linking agent, compatible with (A) and having an average of at least three silicon-bonded hydrogen atoms per molecule with the hydrogen radicals being bonded to separate silicon atoms; (D) an effective amount of an inhibitor for the metal, hydrosilylation catalyst; and wherein the composition contains 0.8 to 1.5 silicon-bonded hydrogen radicals for every unsaturated radical in the composition.
Claim 3
Dependent Claim 93 words
A curable coating composition in accordance with claim 1 wherein (A) has a viscosity at 25° C. of 100 to 1000 centistokes and is a dimethylvinylsiloxane-endblocked polydiorganosiloxane polymer consisting essentially of dimethylsiloxane units and alkenylmethylsiloxane units wherein the alkenyl radicals are represented by the formula --R(CH 2 ) m CH═CH 2 wherein R denotes --(CH 2 ) n -- or --(CH 2 ) p CH═CH-- and m has the value of 1, 2, or 3; n has the value of 3 or 6; and p has the value of 3, 4, or 5.
Claim 4
Dependent Claim 70 words
A curable coating composition in accordance with claim 1 wherein the unsaturated radicals in (A) are alkenyl radicals represented by the formula --R(CH 2 ) m CH═CH 2 wherein R denotes --(CH 2 ) n -- or --(CH 2 ) p CH═CH-- and m has the value of 1, 2, or 3; n has the value of 3 or 6; and p has the value of 3, 4, or 5.
Claim 5
Dependent Claim 49 words
A curable coating composition in accordance with claim 3 wherein the siloxane units of (A) are selected independently from the group consisting of dimethylsiloxane units, trimethylsiloxane units, alkenylmethylsiloxane units, and alkenyldimethylsiloxane units and the composition contains 0.9 to 1.2 silicon-bonded hydrogen radicals for every unsaturated radical in the composition.
Claim 6
Dependent Claim 39 words
A curable coating composition in accordance with claim 4 wherein (A) has a viscosity at 25° C. of 100 to 1000 centistokes and the alkenyl radicals are selected from the group consisting of 5-hexenyl, 7-octenyl, 9-decenyl, and 5,9-decadienyl radicals.
Claim 7
Dependent Claim 30 words
A curable coating composition in accordance with claim 5 wherein (A) has a viscosity at 25° C. of 200 to 600 centistokes and the alkenyl radical is the 5-hexenyl radical.
Claim 8
Dependent Claim 20 words
A curable coating composition in accordance with claim 6 wherein (A) is a 5-hexenyldimethylsiloxane-endblocked copolymer of dimethylsiloxane and 5-hexenylmethylsiloxane units.
Claim 9
Dependent Claim 22 words
A curable coating composition in accordance with claim 7 wherein 1.0 to 4.0 mole percent of the diorganosiloxane units are 5-hexenylmethylsiloxane units.
Claim 10
Dependent Claim 15 words
A curable coating composition in accordance with claim 8 wherein (B) is a platinum-containing catalyst.
Claim 11
Dependent Claim 18 words
A curable coating composition in accordance with claim 9 wherein (B) is a complex of platinum and cyclopolyvinylmethylsiloxane.
Claim 12
Dependent Claim 260 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 release composition on the surface of the substrate wherein the composition comprises (A) a triorganosiloxane-endblocked polydiorganosiloxane polymer having a viscosity at 25° C. of at least 25 centistokes, wherein 90 to 99.5 percent of all organic radicals are methyl, from 0.5 to 10 percent of all organic radicals are unsaturated radicals independently selected from the group consisting of the vinyl radical and higher alkenyl radicals represented by the formula --R(CH 2 ) m CH═CH 2 wherein R denotes --(CH 2 ) n -- or --(CH 2 ) p CH═CH-- and m has the value of 1, 2, or 3; n has the value of 3 or 6; and p has the value of 3, 4, or 5, with the proviso that at least 50 mole percent of the unsaturated radicals are higher alkenyl radicals; (B) a catalytic amount of a metal, hydrosilylation catalyst; (C) a methylhydrogenpolysiloxane cross-linking agent, compatible with (A) and having an average of at least three silicon-bonded hydrogen atoms per molecule with the hydrogen radicals being bonded to separate silicon atoms; (D) an effective amount of an inhibitor for the metal, hydrosilylation catalyst; and wherein the composition contains 0.8 to 1.5 silicon-bonded hydrogen radicals for every unsaturated radical in the composition; (II) curing the silicone release composition with an effective amount of heat; (III) applying, on line, an adhesive to the silicone surface of the substrate.
Claim 13
Dependent Claim 260 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 release composition on the surface of the substrate wherein the composition comprises (A) a triorganosiloxane-endblocked polydiorganosiloxane polymer having a viscosity at 25° C. of at least 25 centistokes, wherein 90 to 99.5 percent of all organic radicals are methyl, from 0.5 to 10 percent of all organic radicals are unsaturated radicals independently selected from the group consisting of the vinyl radical and higher alkenyl radicals represented by the formula --R(CH 2 ) m CH═CH 2 wherein R denotes --(CH 2 ) n -- or --(CH 2 ) p CH═CH-- and m has the value of 1, 2, or 3; n has the value of 3 or 6; and p has the value of 3, 4, or 5, with the proviso that at least 50 mole percent of the unsaturated radicals are higher alkenyl radicals; (B) a catalytic amount of a metal, hydrosilylation catalyst; (C) a methylhydrogenpolysiloxane cross-linking agent, compatible with (A) and having an average of at least three silicon-bonded hydrogen atoms per molecule with the hydrogen radicals being bonded to separate silicon atoms; (D) an effective amount of an inhibitor for the metal, hydrosilylation catalyst; and wherein the composition contains 0.8 to 1.5 silicon-bonded hydrogen radicals for every unsaturated radical in the composition; (II) curing the silicone release composition with an effective amount of heat; (III) applying, on line, an adhesive to the silicone surface of the substrate.
Claim 14
Dependent Claim 91 words
A process in accordance with claim 11 wherein (A) has a viscosity at 25° C. of 100 to 1000 centistokes and is a dimethylvinylsiloxane-endblocked polydiorganosiloxane polymer consisting essentially of dimethylsiloxane units and alkenylmethylsiloxane units wherein the alkenyl radicals are represented by the formula --R(CH 2 ) m CH═CH 2 wherein R denotes --(CH 2 ) n -- or --(CH 2 ) p CH═CH-- and m has the value of 1, 2, or 3; n has the value of 3 or 6; and p has the value of 3, 4, or 5.
Claim 15
Dependent Claim 68 words
A process in accordance with claim 11 wherein the unsaturated radicals in (A) are alkenyl radicals represented by the formula --R(CH 2 ) m CH═CH 2 wherein R denotes --(CH 2 ) n -- or --(CH 2 ) p CH═CH-- and m has the value of 1, 2, or 3; n has the value of 3 or 6; and p has the value of 3, 4, or 5.
Claim 16
Dependent Claim 47 words
A process in accordance with claim 13 wherein the siloxane units of (A) are selected independently from the group consisting of dimethylsiloxane units, trimethylsiloxane units, alkenylmethylsiloxane units, and alkenyldimethylsiloxane units and the composition contains 0.9 to 1.2 silicon-bonded hydrogen radicals for every unsaturated radical in the composition.
Claim 17
Dependent Claim 37 words
A process in accordance with claim 14 wherein (A) has a viscosity at 25° C. of 100 to 1000 centistokes and the alkenyl radicals are selected from the group consisting of 5-hexenyl, 7-octenyl, 9-decenyl, and 5,9-decadienyl radicals.
Claim 18
Dependent Claim 28 words
A process in accordance with claim 15 wherein (A) has a viscosity at 25° C. of 200 to 600 centistokes and the alkenyl radical is the 5-hexenyl radical.
Claim 19
Dependent Claim 18 words
A process in accordance with claim 16 wherein (A) is a 5-hexenyldimethylsiloxane-endblocked copolymer of dimethylsiloxane and 5-hexenylmethylsiloxane units.
Claim 20
Dependent Claim 20 words
A process in accordance with claim 17 wherein 1.0 to 4.0 mole percent of the diorganosiloxane units are 5-hexenylmethylsiloxane units.
Claim 21
Dependent Claim 13 words
A process in accordance with claim 18 wherein (B) is a platinum-containing catalyst.
Claim 22
Dependent Claim 16 words
A process in accordance with claim 19 wherein (B) is a complex of platinum and cyclopolyvinylmethylsiloxane.
Claim 23
Dependent Claim 256 words
In a process for preparing a laminate of a substrate and adhesive wherein the adhesive will release from the substrate, the process comprising coating a curable silicone release composition on a surface of the substrate, thereafter curing the silicone composition, and applying an adhesive to the silicone surface of the substrate, the improvement comprising coating as the curable silicone release composition, a composition comprising (A) a triorganosiloxane-endblocked polydiorganosiloxane polymer having a viscosity at 25° C. of at least 25 centistokes, wherein 90 to 99.5 percent of all organic radicals are methyl, from 0.5 to 10 percent of all organic radicals are unsaturated radicals independently selected from the group consisting of the vinyl radical and higher alkenyl radicals represented by the formula --R(CH 2 ) m CH═CH 2 wherein R denotes --(CH 2 ) n -- or --(CH 2 ) p CH═CH-- and m has the value of 1, 2, or 3; n has the value of 3 or 6; and p has the value of 3, 4, or 5, with the proviso that at least 50 mole percent of the unsaturated radicals are higher alkenyl radicals; (B) a catalytic amount of a metal, hydrosilylation catalyst; (C) a methylhydrogenpolysiloxane cross-linking agent, compatible with (A) and having an average of at least three silicon-bonded hydrogen atoms per molecule with the hydrogen radicals being bonded to separate silicon atoms; (D) an effective amount of an inhibitor for the metal, hydrosilylation catalyst; and wherein the composition contains 0.8 to 1.5 silicon-bonded hydrogen radicals for every unsaturated radical in the composition.
Claim 24
Dependent Claim 256 words
In a process for preparing a laminate of a substrate and adhesive wherein the adhesive will release from the substrate, the process comprising coating a curable silicone release composition on a surface of the substrate, thereafter curing the silicone composition, and applying an adhesive to the silicone surface of the substrate, the improvement comprising coating as the curable silicone release composition, a composition comprising (A) a triorganosiloxane-endblocked polydiorganosiloxane polymer having a viscosity at 25° C. of at least 25 centistokes, wherein 90 to 99.5 percent of all organic radicals are methyl, from 0.5 to 10 percent of all organic radicals are unsaturated radicals independently selected from the group consisting of the vinyl radical and higher alkenyl radicals represented by the formula --R(CH 2 ) m CH═CH 2 wherein R denotes --(CH 2 ) n -- or --(CH 2 ) p CH═CH-- and m has the value of 1, 2, or 3; n has the value of 3 or 6; and p has the value of 3, 4, or 5, with the proviso that at least 50 mole percent of the unsaturated radicals are higher alkenyl radicals; (B) a catalytic amount of a metal, hydrosilylation catalyst; (C) a methylhydrogenpolysiloxane cross-linking agent, compatible with (A) and having an average of at least three silicon-bonded hydrogen atoms per molecule with the hydrogen radicals being bonded to separate silicon atoms; (D) an effective amount of an inhibitor for the metal, hydrosilylation catalyst; and wherein the composition contains 0.8 to 1.5 silicon-bonded hydrogen radicals for every unsaturated radical in the composition.
Claim 25
Dependent Claim 91 words
A process in accordance with claim 21 wherein (A) has a viscosity at 25° C. of 100 to 1000 centistokes and is a dimethylvinylsiloxane-endblocked polydiorganosiloxane polymer consisting essentially of dimethylsiloxane units and alkenylmethylsiloxane units wherein the alkenyl radicals are represented by the formula --R(CH 2 ) m CH═CH 2 wherein R denotes --(CH 2 ) n -- or --(CH 2 ) p CH═CH-- and m has the value of 1, 2, or 3; n has the value of 3 or 6; and p has the value of 3, 4, or 5.
Claim 26
Dependent Claim 68 words
A process in accordance with claim 21 wherein the unsaturated radicals in (A) are alkenyl radicals represented by the formula --R(CH 2 ) m CH═CH 2 wherein R denotes --(CH 2 ) n -- or --(CH 2 ) p CH═CH-- and m has the value of 1, 2, or 3; n has the value of 3 or 6; and p has the value of 3, 4, or 5.
Claim 27
Dependent Claim 47 words
A process in accordance with claim 23 wherein the siloxane units of (A) are selected independently from the group consisting of dimethylsiloxane units, trimethylsiloxane units, alkenylmethylsiloxane units, and alkenyldimethylsiloxane units and the composition contains 0.9 to 1.2 silicon-bonded hydrogen radicals for every unsaturated radical in the composition.
Claim 28
Dependent Claim 37 words
A process in accordance with claim 24 wherein (A) has a viscosity at 25° C. of 100 to 1000 centistokes and the alkenyl radicals are selected from the group consisting of 5-hexenyl, 7-octenyl, 9-decenyl, and 5,9-decadienyl radicals.
Claim 29
Dependent Claim 28 words
A process in accordance with claim 25 wherein (A) has a viscosity at 25° C. of 200 to 600 centistokes and the alkenyl radical is the 5-hexenyl radical.
Claim 30
Dependent Claim 18 words
A process in accordance with claim 26 wherein (A) is a 5-hexenyldimethylsiloxane-endblocked copolymer of dimethylsiloxane and 5-hexenylmethylsiloxane units.
Claim 31
Dependent Claim 20 words
A process in accordance with claim 27 wherein 1.0 to 4.0 mole percent of the diorganosiloxane units are 5-hexenylmethylsiloxane units.
Claim 32
Dependent Claim 13 words
A process in accordance with claim 28 wherein (B) is a platinum-containing catalyst.
Claim 33
Dependent Claim 16 words
A process in accordance with claim 29 wherein (B) is a complex of platinum and cyclopolyvinylmethylsiloxane.

References Cited (Backward Citations)

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GB1518371A Cited
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USPTO Annuity & Maintenance Windows

Annuity Stage Window Opens Payment Deadline Surcharge Period Until Estimated Fee Status
3.5 Years (Year 4) 1989-09-01 1990-03-03 1990-09-02 $2000.00 Window Closed / Lapsed
7.5 Years (Year 8) 1993-09-01 1994-03-03 1994-09-02 $3760.00 Window Closed / Lapsed
11.5 Years (Year 12) 1997-09-01 1998-03-03 1998-09-02 $7700.00 Window Closed / Lapsed

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