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US4603168A Expired / Lapsed US ⏱️ 0.0 years remaining

Method for curing organopolysiloxane compositions and the compositions

Assignee: DuPont Toray Specialty Materials KK
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Filing: 1985-02-19
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Granted: 1986-07-29
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Expires: 2005-02-19
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Abstract

Abstract A method of curing certain organopolysiloxane compositions by a combination of heat and exposure to ultraviolet radiation or electron beam provides the ability to use lower temperatures than heat cures alone and shorter cure times than ultraviolet radiation or electron beam alone. The organopolysiloxane compositions are addition-curable and are made up of alkenyl-containing organopolysiloxane, organohydrogensiloxane, a platinum catalyst, an addition-reaction inhibitor selected from alkynol, 3-methyl-3-pentene-1-yne, 3,5-dimethyl-3-hexene-1-yne, methylvinylsiloxane cyclics, benzotriazole, and mixtures thereof, and a photosensitizer.

Inventors

  • 👤 Shosaku Sasaki
  • 👤 Yuji Hamada

Bibliographic Details

Application Number —
Jurisdiction US
Data Source google_patents
Last Synchronized 2026-11-04 01:26
CPC Classifications
C; C08; C08J; C08J3/00; C08J3/28; C08L; C08L83/00; C08L83/04; C08G; C08G77/00; C08G77/04; C08G77/12; C08G77/14; C08G77/16; C08G77/20; C08G77/22; C08G77/24; C08G77/42; C08G77/44; C08G77/70; C08J2383/00; C08J2383/04

Claims Analysis

Total Claims: 24
Claim 1
Independent Claim 134 words
A method for curing organopolysiloxane compositions consisting essentially of heating and exposing to ultraviolet radiation of an electron beam a photosensitizer-containing organopolysiloxane composition which consists essentially of (A) 100 parts by weight of addition-curable organopolysiloxane composition which consists essentially of (1) organopolysiloxane containing at least two silicon-bonded alkenyl groups per molecule and other organic groups when present are selected from the group consisting of alkyl groups, halogenated alkyl groups, aryl groups, aralkyl groups, and alkaryl groups, (2) organohydrogenpolysiloxane containing at least two organohydrogensiloxane or hydrogensiloxane units per molecule, (3) a platinum catalyst selected from the group consisting of chloroplatinic acid-vinyl-siloxane coordination compound and alcohol-modified chloroplatinic acid, (4) an addition-reaction retarder selected from the group consisting of alkynol, 3-methyl-3-pentene-1-yne, 3,5-dimethyl-3-hexene-1-yne, methylvinylsiloxane cyclics, benzotriazole, and mixtures thereof, and (B) 0.001 to 30 parts by weight photosensitizer.
Claim 2
Independent Claim 134 words
A method for curing organopolysiloxane compositions consisting essentially of heating and exposing to ultraviolet radiation of an electron beam a photosensitizer-containing organopolysiloxane composition which consists essentially of (A) 100 parts by weight of addition-curable organopolysiloxane composition which consists essentially of (1) organopolysiloxane containing at least two silicon-bonded alkenyl groups per molecule and other organic groups when present are selected from the group consisting of alkyl groups, halogenated alkyl groups, aryl groups, aralkyl groups, and alkaryl groups, (2) organohydrogenpolysiloxane containing at least two organohydrogensiloxane or hydrogensiloxane units per molecule, (3) a platinum catalyst selected from the group consisting of chloroplatinic acid-vinyl-siloxane coordination compound and alcohol-modified chloroplatinic acid, (4) an addition-reaction retarder selected from the group consisting of alkynol, 3-methyl-3-pentene-1-yne, 3,5-dimethyl-3-hexene-1-yne, methylvinylsiloxane cyclics, benzotriazole, and mixtures thereof, and (B) 0.001 to 30 parts by weight photosensitizer.
Claim 3
Dependent Claim 38 words
The method according to claim 1 in which (1) and (2) are present in amounts sufficient to provide from 0.1 to 10 moles of organohydrogensiloxane and hydrogensiloxane units in (2) per one mole of alkenyl group in (1).
Claim 4
Dependent Claim 33 words
The method according to claim 1 in which (3) the platinum catalyst is present in an amount of from 0.1 to 1000 parts by weight per million parts by weight of platinum element.
Claim 5
Dependent Claim 29 words
The method according to claim 1 in which (4) is present in an amount of from 0.05 to 10 parts by weight per 100 parts by weight of (1).
Claim 6
Dependent Claim 22 words
The method according to claim 1 in which (B) is present in an amount of from 0.05 to 20 parts by weight.
Claim 7
Dependent Claim 196 words
The method according to claim 2 in which (1) is a polydiorganosiloxane consisting essentially of diorganosiloxane units selected from the group consisting of dimethylsiloxane units, methylphenylsiloxane units, methylvinylsiloxane units, and mixtures thereof, said polydiorganosiloxane is endblocked with dimethylvinylsiloxy units, trimethylsiloxy units, or silicon-bonded hydroxyl groups, and has a vinyl content of from 0.5 to 3 weight percent; (2) is a trimethylsiloxy endblocked polysiloxane containing methylhydrogensiloxane units and optionally dimethylsiloxane units, has a viscosity of from 0.005 to 0.05 Pa·s at 25° C., and is present in an amount of from 2 to 10 parts by weight based on 100 parts by weight of (1); (3) is present in an amount of from 50 to 200 parts by weight of platinum element per million parts by weight of (1); (4) is an alkynol or 3-methyl-3-pentene-1-yne and is present in an amount of from 0.1 to 1.0 part by weight per 100 parts by weight of (1); and (B) is a photosensitizer selected from the group consisting of 4-allylacetophenone, benzophenone, benzoin ethyl ether, and benzil dimethyl ketal, and is present in an amount of from 0.1 to 5 parts by weight per 100 parts by weight of (A).
Claim 8
Dependent Claim 12 words
The method according to claim 6 in which (4) is an alkynol.
Claim 9
Dependent Claim 12 words
The method according to claim 7 in which the alkynol is 3-methyl-1-butyne-3-ol.
Claim 10
Dependent Claim 12 words
The method according to claim 7 in which the alkynol is phenylbutynol.
Claim 11
Dependent Claim 12 words
The method according to claim 7 in which the alkynol is 3,5-dimethyl-1-hexyne-3-ol.
Claim 12
Dependent Claim 11 words
The method according to claim 6 in which (4) is 3-methyl-3-pentene-1-yne.
Claim 13
Independent Claim 135 words
A method for curing organopolysiloxane compositions comprising a combination of heating and exposing to ultraviolet radiation or an electron beam a photosensitizer-containing organopolysiloxane composition which consists essentially of (A) 100 parts by weight of addition-curable organopolysiloxane composition which consists essentially of (1) organopolysiloxane containing at least two silicon-bonded alkenyl groups per molecule and other organic groups when present are selected from the group consisting of alkyl groups, halogenated alkyl groups, aryl groups, aralkyl groups, and alkaryl groups, (2) organohydrogenpolysiloxane containing at least two organohydrogensiloxane or hydrogensiloxane units per molecule, (3) a platinum catalyst selected from the group consisting of chloroplatinic acid-vinylsiloxane coordination compound and alcohol-modified chloroplatinic acid, (4) an addition-reaction retarder selected from the group consisting of alkynol, 3-methyl-3-pentene-1-yne, 3,5-dimethyl-3-hexene-1-yne, methylvinylsiloxane cyclics, benzotriazole, and mixtures thereof, and (B) 0.001 to 30 parts by weight photosensitizer.
Claim 14
Independent Claim 135 words
A method for curing organopolysiloxane compositions comprising a combination of heating and exposing to ultraviolet radiation or an electron beam a photosensitizer-containing organopolysiloxane composition which consists essentially of (A) 100 parts by weight of addition-curable organopolysiloxane composition which consists essentially of (1) organopolysiloxane containing at least two silicon-bonded alkenyl groups per molecule and other organic groups when present are selected from the group consisting of alkyl groups, halogenated alkyl groups, aryl groups, aralkyl groups, and alkaryl groups, (2) organohydrogenpolysiloxane containing at least two organohydrogensiloxane or hydrogensiloxane units per molecule, (3) a platinum catalyst selected from the group consisting of chloroplatinic acid-vinylsiloxane coordination compound and alcohol-modified chloroplatinic acid, (4) an addition-reaction retarder selected from the group consisting of alkynol, 3-methyl-3-pentene-1-yne, 3,5-dimethyl-3-hexene-1-yne, methylvinylsiloxane cyclics, benzotriazole, and mixtures thereof, and (B) 0.001 to 30 parts by weight photosensitizer.
Claim 15
Independent Claim 136 words
A method for curing organopolysiloxane compositions consisting of a combination of heating and exposing to ultraviolet radiation or an electron beam a photosensitizer-containing organopolysiloxane composition which consists essentially of (A) 100 parts by weight of addition-curable organopolysiloxane composition which consists essentially of (1) organopolysiloxane containing at least two silicon-bonded alkenyl groups per molecule and other organic groups when present are selected from the group consisting of alkyl groups, halogenated alkyl groups, aryl groups, aralkyl groups, and alkaryl groups, (2) organohydrogenpolysiloxane containing at least two organohydrogensiloxane or hydrogensiloxane units per molecule, (3) a platinum catalyst selected from the group consisting of chloroplatinic acid-vinylsiloxane coordination compound and alcohol-modified chloroplatinic acid, (4) an addition-reaction retarder selected from the group consisting of alkynol, 3-methyl-3-pentene-1-yne, 3,5-dimethyl-3-hexene-1-yne, methylvinylsiloxane cyclics, benzotriazole, and mixtures thereof, and (B) 0.001 to 30 parts by weight photosensitzer.
Claim 16
Independent Claim 136 words
A method for curing organopolysiloxane compositions consisting of a combination of heating and exposing to ultraviolet radiation or an electron beam a photosensitizer-containing organopolysiloxane composition which consists essentially of (A) 100 parts by weight of addition-curable organopolysiloxane composition which consists essentially of (1) organopolysiloxane containing at least two silicon-bonded alkenyl groups per molecule and other organic groups when present are selected from the group consisting of alkyl groups, halogenated alkyl groups, aryl groups, aralkyl groups, and alkaryl groups, (2) organohydrogenpolysiloxane containing at least two organohydrogensiloxane or hydrogensiloxane units per molecule, (3) a platinum catalyst selected from the group consisting of chloroplatinic acid-vinylsiloxane coordination compound and alcohol-modified chloroplatinic acid, (4) an addition-reaction retarder selected from the group consisting of alkynol, 3-methyl-3-pentene-1-yne, 3,5-dimethyl-3-hexene-1-yne, methylvinylsiloxane cyclics, benzotriazole, and mixtures thereof, and (B) 0.001 to 30 parts by weight photosensitzer.
Claim 17
Dependent Claim 20 words
The method according to claim 1 in which the heating is at a temperature of from 50° to 100° C.
Claim 18
Dependent Claim 113 words
A composition consisting essentially of (A) 100 parts by weight of addition-curable organopolysiloxane composition which consists essentially of (1) organopolysiloxane containing at least two silicon-bonded alkenyl groups per molecule and other organic groups when present are selected from the group consisting of alkyl groups, halogenated alkyl groups, aryl groups, aralkyl groups, and alkaryl groups, (2) organohydrogenpolysiloxane containing at least two organohydrogensiloxane or hydrogensiloxane units per molecule, (3) a platinum catalyst selected from the group consisting of chloroplatinic acid-vinylsiloxane coordination compound and alcohol-modified chloroplatinic acid, and (4) an addition-reaction retarder selected from the group consisting of alkynol, 3-methyl-3-pentene-1-yne, 3,5-dimethyl-3-hexene-1-yne, methylvinylsiloxane cyclics, benzotriazole, and mixtures thereof, and (B) 0.001 to 30 parts by weight photosensitizer.
Claim 19
Dependent Claim 113 words
A composition consisting essentially of (A) 100 parts by weight of addition-curable organopolysiloxane composition which consists essentially of (1) organopolysiloxane containing at least two silicon-bonded alkenyl groups per molecule and other organic groups when present are selected from the group consisting of alkyl groups, halogenated alkyl groups, aryl groups, aralkyl groups, and alkaryl groups, (2) organohydrogenpolysiloxane containing at least two organohydrogensiloxane or hydrogensiloxane units per molecule, (3) a platinum catalyst selected from the group consisting of chloroplatinic acid-vinylsiloxane coordination compound and alcohol-modified chloroplatinic acid, and (4) an addition-reaction retarder selected from the group consisting of alkynol, 3-methyl-3-pentene-1-yne, 3,5-dimethyl-3-hexene-1-yne, methylvinylsiloxane cyclics, benzotriazole, and mixtures thereof, and (B) 0.001 to 30 parts by weight photosensitizer.
Claim 20
Dependent Claim 38 words
The composition according to claim 15 in which (1) and (2) are present in amounts sufficient to provide from 0.1 to 10 moles of organohydrogensiloxanes and hydrogensiloxane units in (2) per one mole of alkenyl group in (1).
Claim 21
Dependent Claim 195 words
The composition according to claim 16 in which (1) is a polydiorganosiloxane consisting essentially of diorganosiloxane units selected from the group consisting of dimethylsiloxane units, methylphenylsiloxane units, methylvinylsiloxane units, and mixtures thereof, said polydiorganosiloxane is endblocked with dimethylvinylsiloxy units, trimethylsiloxy units, or silicon-bonded hydroxyl groups, and has a vinyl content of from 0.5 to 3 weight percent; (2) is a trimethylsiloxy endblocked polysiloxane containing methylhydrogensiloxane units and optionally dimethylsiloxane units, has a viscosity of from 0.005 to 0.05 Pa·s at 25° C., and is present in an amount of from 2 to 10 parts by weight based on 100 parts by weight of (1); (3) is present in an amount of from 50 to 200 parts by weight platinum element per million parts by weight of (1); (4) is an alkynol or 3-methyl-3-pentene-1-yne and is present in an amount of from 0.1 to 1.0 part by weight per 100 parts by weight of (1); and (B) is a photosensitizer selected from the group consisting of 4-allylacetophenone, benzophenone, benzoin ethyl ether, and benzil dimethyl ketal, and is present in an amount of from 0.1 to 5 parts by weight per 100 parts by weight of (A).
Claim 22
Dependent Claim 12 words
The composition according to claim 17 in which (4) is an alkynol.
Claim 23
Dependent Claim 18 words
The method in accordance with claim 1 in which the composition is cured by heating and ultraviolet radiation.
Claim 24
Dependent Claim 18 words
The method in accordance with claim 1 in which the composition is cured by heating and electron beam.

References Cited (Backward Citations)

GB1433461A Cited
US4064027A Cited
JPS55125123A Cited
US4530879A Cited
JPH0513709A Cited
JPH061397A Cited

USPTO Annuity & Maintenance Windows

Annuity Stage Window Opens Payment Deadline Surcharge Period Until Estimated Fee Status
3.5 Years (Year 4) 1989-07-28 1990-01-27 1990-07-29 $2000.00 Window Closed / Lapsed
7.5 Years (Year 8) 1993-07-28 1994-01-27 1994-07-29 $3760.00 Window Closed / Lapsed
11.5 Years (Year 12) 1997-07-28 1998-01-27 1998-07-29 $7700.00 Window Closed / Lapsed

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