US5124375A
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Process for preparing organosilicon prepolymers and polymers
Assignee: National Starch and Chemical Investment Holding Corp
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Filing: 1990-01-05
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Granted: 1992-06-23
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Expires: 2010-01-05
Abstract
Abstract A novel organosilicon prepolymer, which is the partial reaction product of (a) a cyclic polysiloxane or a tetrahedral siloxysilane containing at least two hydrosilane groups and (b) a polycyclic polyene having in its rings at least two chemically distinguishable carbon-carbon double bonds, wherein the ratio of carbon-carbon double bonds in the rings of (b) to hydrosilane groups in (a) is greater than 0.5:1 and up to 1.8:1, and at least one of the compounds (a) and (b) has more than two reactive sites, a method for making the organosilicon prepolymer, and a method for preparing an organosilicon polymer therefrom, are disclosed.
Inventors
- 👤 Raymond T. Leibfried
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-06 06:34
CPC Classifications
C; C08; C08L; C08L83/00; C08L83/14; C08G; C08G77/00; C08G77/48
Claims Analysis
Total Claims: 25
Claim 1
Independent Claim
98 words
A process for preparing an organosilicon prepolymer comprising partially reacting, in the presence of a hydrosilation catalyst, (a) a cyclic polysiloxane or tetrahedral siloxysilane containing at least two .tbd.SiH groups and (b) a polycyclic hydrocarbon polyene having in its rings at least two chemically distinguishable carbon-carbon double bonds, wherein 30% to 65% of the .tbd.SiH groups are reacted, the ratio of carbon-carbon double bonds in the rings of (b) to .tbd.SiH groups in (a) is greater than 0.5:1 and up to 1.8:1, and at least one of the compounds (a) and (b) has more than two reactive sites.
Claim 2
Dependent Claim
98 words
A process for preparing an organosilicon prepolymer comprising partially reacting, in the presence of a hydrosilation catalyst, (a) a cyclic polysiloxane or tetrahedral siloxysilane containing at least two .tbd.SiH groups and (b) a polycyclic hydrocarbon polyene having in its rings at least two chemically distinguishable carbon-carbon double bonds, wherein 30% to 65% of the .tbd.SiH groups are reacted, the ratio of carbon-carbon double bonds in the rings of (b) to .tbd.SiH groups in (a) is greater than 0.5:1 and up to 1.8:1, and at least one of the compounds (a) and (b) has more than two reactive sites.
Claim 3
Dependent Claim
102 words
The process of forming an organosilicon prepolymer as claimed in claim 1, wherein the silicon-containing reactant (a) is: ##STR4## wherein R, which can be the same or different, is hydrogen or a substituted or unsubstituted alkyl, alkoxy, aromatic or aryloxy radical, n is an integer from 3 to about 20, and R is hydrogen on at least two of the silicon atoms in the molecule; or is: ##STR5## wherein R is as defined above and is hydrogen on at least two silicon atoms in the molecule, and the polycyclic polyene is selected from the group consisting of dicyclopentadiene, tricyclopentadiene and methyl dicyclopentadiene.
Claim 4
Dependent Claim
48 words
The process of forming an organosilicon prepolymer as claimed in claim 1, wherein the hydrosilation catalyst is a platinum-containing catalyst and the ratio of carbon-carbon double bonds in the rings of (b) to .tbd.SiH groups in (a) is in the range of about 0.7:1 up to about 1.3:1.
Claim 5
Dependent Claim
48 words
The process of forming an organosilicon prepolymer as claimed in claim 2, wherein the hydrosilation catalyst is chloroplatinic acid and the ratio of carbon-carbon double bonds in the rings of (b) to .tbd.SiH groups in (a) is in the range of from about 0.8:1 up to about 1.1:1.
Claim 6
Dependent Claim
23 words
The process of claim 1 wherein the reaction is discontinued at the point where 30 to 65% of the .tbd.SiH groups have reacted.
Claim 7
Dependent Claim
44 words
The process of forming a crosslinked organosilicon polymer consisting essentially of (a) preparing an organosilicon prepolymer according to the process of claim 1 and (b) curing, in the presence of a hydrosilation catalyst, the organosilicon prepolymer so as to form a crosslinked organosilicon polymer.
Claim 8
Dependent Claim
124 words
The process of forming a crosslinked organosilicon polymer consisting essentially of providing an organosilicon prepolymer, wherein the organosilicon prepolymer is the partial reaction product of (a) a cyclic polysiloxane or a tetrahedral siloxysilane containing at least two .tbd.SiH groups and (b) a polycyclic hydrocarbon polyene having in its rings at least two chemically distinguishable carbon-carbon double bonds, the ratio of carbon-carbon double bonds in the rings of (b) to .tbd.SiH groups in (a) is greater than 0.5:1 and up to 1.8:1, at least one of the compounds (a) and (b) has more than two reactive sites, and 30 to 65% of the .tbd.SiH groups are reacted and curing the organosilicon prepolymer in the presence of a hydrosilation catalyst to form a cross-linked organosilicon polymer.
Claim 9
Dependent Claim
124 words
The process of forming a crosslinked organosilicon polymer consisting essentially of providing an organosilicon prepolymer, wherein the organosilicon prepolymer is the partial reaction product of (a) a cyclic polysiloxane or a tetrahedral siloxysilane containing at least two .tbd.SiH groups and (b) a polycyclic hydrocarbon polyene having in its rings at least two chemically distinguishable carbon-carbon double bonds, the ratio of carbon-carbon double bonds in the rings of (b) to .tbd.SiH groups in (a) is greater than 0.5:1 and up to 1.8:1, at least one of the compounds (a) and (b) has more than two reactive sites, and 30 to 65% of the .tbd.SiH groups are reacted and curing the organosilicon prepolymer in the presence of a hydrosilation catalyst to form a cross-linked organosilicon polymer.
Claim 10
Dependent Claim
87 words
The process of forming a crosslinked organosilicon polymer as claimed in claim 7, wherein the silicon-containing reactant (a) is: ##STR6## wherein R, which can be the same or different, is hydrogen or a substituted or unsubstituted alkyl, alkoxy, aromatic or aryloxy radical, n is an integer from 3 to about 20, and R is hydrogen on at least two of the silicon atoms in the molecule; or is: ##STR7## wherein R is as defined above and is hydrogen on at least two silicon atoms in the molecule.
Claim 11
Dependent Claim
29 words
The process of forming a crosslinked organosilicon polymer as claimed in claim 8, wherein the polycyclic polyene is selected from the group consisting of dicyclopentadiene, tricyclopentadiene and methyl dicyclopentadiene.
Claim 12
Dependent Claim
49 words
The process of forming a crosslinked organosilicon polymer as claimed in claim 7, wherein the hydrosilation catalyst is a platinum-containing catalyst and the ratio of carbon-carbon double bonds in the rings of (b) to .tbd.SiH groups in (a) is in the range of about 0.7:1 up to about 1.3:1.
Claim 13
Dependent Claim
49 words
The process of forming a crosslinked organosilicon polymer as claimed in claim 9, wherein the hydrosilation catalyst is chloroplatinic acid and the ratio of carbon-carbon double bonds in the rings of (b) to .tbd.SiH groups in (a) is in the range of from about 0.8:1 up to about 1.1:1.
Claim 14
Dependent Claim
159 words
The process of forming a fiber reinforced composite material comprising: (i) impregnating with an organosilicon prepolymer up to 80%, by weight of the resultant fiber reinforced composite material, fibrous reinforcement selected from the group consisting of glass, carbon, metallic, ceramic or synthetic polymer fibers, or fiber mat; and (ii) curing, in the presence of a hydrosilation catalyst, the prepolymer to form a fiber reinforced composite material, wherein the organosilicon prepolymer is the partial reaction product of (a) a cyclic polysiloxane or a tetrahedral siloxysilane containing at least two .tbd.SiH groups and (b) a polycyclic hydrocarbon polyene having in its rings at least two chemically distinguishable carbon-carbon double bonds, wherein the ratio of carbon-carbon double bonds in the rings of (b) to .tbd.SiH groups in (a) is greater than 0.5:1 and up to 1.8:1, at least one of the compounds (a) and (b) has more than two reactive sites and wherein 30% to 65% of the .tbd.SiH groups are reacted.
Claim 15
Dependent Claim
159 words
The process of forming a fiber reinforced composite material comprising: (i) impregnating with an organosilicon prepolymer up to 80%, by weight of the resultant fiber reinforced composite material, fibrous reinforcement selected from the group consisting of glass, carbon, metallic, ceramic or synthetic polymer fibers, or fiber mat; and (ii) curing, in the presence of a hydrosilation catalyst, the prepolymer to form a fiber reinforced composite material, wherein the organosilicon prepolymer is the partial reaction product of (a) a cyclic polysiloxane or a tetrahedral siloxysilane containing at least two .tbd.SiH groups and (b) a polycyclic hydrocarbon polyene having in its rings at least two chemically distinguishable carbon-carbon double bonds, wherein the ratio of carbon-carbon double bonds in the rings of (b) to .tbd.SiH groups in (a) is greater than 0.5:1 and up to 1.8:1, at least one of the compounds (a) and (b) has more than two reactive sites and wherein 30% to 65% of the .tbd.SiH groups are reacted.
Claim 16
Dependent Claim
88 words
The process of forming a fiber reinforced composite material as claimed in claim 12, wherein the silicon-containing reactant (a) is: ##STR8## wherein R, which can be the same or different, is hydrogen or a substituted or unsubstituted alkyl, alkoxy, aromatic or aryloxy radical, n is an integer from 3 to about 20, and R is hydrogen on at least two of the silicon atoms in the molecule; or is: ##STR9## wherein R is as defined above and is hydrogen on at least two silicon atoms in the molecule.
Claim 17
Dependent Claim
30 words
The process of forming a fiber reinforced composite material as claimed in claim 13, wherein the polycyclic polyene is selected from the group consisting of dicyclopentadiene, tricyclopentadiene and methyl dicyclopentadiene.
Claim 18
Dependent Claim
50 words
The process of forming a fiber reinforced composite material as claimed in claim 12, wherein the hydrosilation catalyst is a platinum-containing catalyst and the ratio of carbon-carbon double bonds in the rings of (b) to .tbd.SiH groups in (a) is in the range of about 0.7:1 up to about 1.3:1.
Claim 19
Dependent Claim
50 words
The process of forming a fiber reinforced composite material as claimed in claim 14, wherein the hydrosilation catalyst is chloroplatinic acid and the ratio of carbon-carbon double bonds in the rings of (b) to .tbd.SiH groups in (a) is in the range of from about 0.8:1 up to about 1.1:1.
Claim 20
Dependent Claim
29 words
The process of forming a fiber reinforced composite material as claimed in claim 12, wherein step (i) comprises charging a mold containing the fiber reinforcement with the organosilicon prepolymer.
Claim 21
Dependent Claim
29 words
The process of forming a fiber reinforced composite material as claimed in claim 12, wherein step (i) comprises injecting the organosilicon prepolymer into a mold containing the fiber reinforcement.
Claim 22
Dependent Claim
165 words
The process of forming a fiber reinforced composite material comprising: (i) forming a prepolymer by partially reacting, in the presence of a hydrosilation catalyst, (a) a cyclic polysiloxane or tetrahedral siloxysilane containing at least two .tbd.SiH groups and (b) a polycyclic hydrocarbon polyene having in its rings at least two chemically distinguishable carbon-carbon double bonds, to the extent that 30% to 65% of the .tbd.SiH groups are reacted, wherein the ratio of carbon-carbon double bonds in the rings of (b) to .tbd.SiH groups in (a) is greater than 0.5:1 and up to 1.8:1, and at least one of the compounds (a) and (b) has more than two reactive sites; (ii) impregnating with the organosilicon prepolymer up to 80%, by weight of the resultant fiber reinforced composite material, fibrous reinforcement selected from the group consisting of glass, carbon, metallic, ceramic or synthetic polymer fibers, or fiber mat; and (iii) curing, in the presence of a hydrosilation catalyst, the prepolymer to form a fiber reinforced composite material.
Claim 23
Dependent Claim
165 words
The process of forming a fiber reinforced composite material comprising: (i) forming a prepolymer by partially reacting, in the presence of a hydrosilation catalyst, (a) a cyclic polysiloxane or tetrahedral siloxysilane containing at least two .tbd.SiH groups and (b) a polycyclic hydrocarbon polyene having in its rings at least two chemically distinguishable carbon-carbon double bonds, to the extent that 30% to 65% of the .tbd.SiH groups are reacted, wherein the ratio of carbon-carbon double bonds in the rings of (b) to .tbd.SiH groups in (a) is greater than 0.5:1 and up to 1.8:1, and at least one of the compounds (a) and (b) has more than two reactive sites; (ii) impregnating with the organosilicon prepolymer up to 80%, by weight of the resultant fiber reinforced composite material, fibrous reinforcement selected from the group consisting of glass, carbon, metallic, ceramic or synthetic polymer fibers, or fiber mat; and (iii) curing, in the presence of a hydrosilation catalyst, the prepolymer to form a fiber reinforced composite material.
Claim 24
Dependent Claim
138 words
The process of forming a fiber reinforced composite material as claimed in claim 12, wherein the silicon-containing reactant (a) is: ##STR10## wherein R, which can be the same or different, is hydrogen or a substituted or unsubstituted alkyl, alkoxy, aromatic or aryloxy radical, n is an integer from 3 to about 20, and R is hydrogen on at least two of the silicon atoms in the molecule; or is: ##STR11## wherein R is as defined above and is hydrogen on at least two silicon atoms in the molecule; the polycyclic polyene is selected from the group consisting of dicyclopentadiene, tricyclopentadiene and methyl dicyclopentadiene; the hydrosilation catalyst is a platinum-containing catalyst; and the ratio of carbon-carbon double bonds in the rings of (b) to .tbd.SiH groups in (a) is in the range of about 0.7:1 up to about 1.3:1.
Claim 25
Dependent Claim
50 words
The process of forming a fiber reinforced composite material as claimed in claim 20, wherein the hydrosilation catalyst is chloroplatinic acid and the ratio of carbon-carbon double bonds in the rings of (b) to .tbd.SiH groups in (a) is in the range of from about 0.8:1 up to about 1.1:1.
References Cited (Backward Citations)
US4902731A
Cited
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| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
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| 3.5 Years (Year 4) | 1995-06-23 | 1995-12-23 | 1996-06-23 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1999-06-23 | 1999-12-23 | 2000-06-23 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 2003-06-23 | 2003-12-23 | 2004-06-23 | $7700.00 | Window Closed / Lapsed |