Patent US5068303A successfully refreshed from Google Patents.
US5068303A
Expired / Lapsed
US
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Organosilicon materials
Assignee: University of Southern Mississippi Research Foundation
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Filing: 1990-09-28
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Granted: 1991-11-26
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Expires: 2010-09-28
Abstract
Abstract A crosslinkable organosilicon prepolymer and a crosslinked organosilicon polymer comprising alternating hydrocarbon and cyclic polysiloxane radicals, which is the hydrosilation reaction product of: (a) at least one polyene having at least two non-aromatic, non-conjugated carbon-carbon double bonds highly reactive in hydrosilation, the carbon-carbon double bonds being either in an alpha, beta or gamma position on a linear carbon moiety, next to two bridgehead positions in a strained polycyclic aliphatic ring structure, or in a cyclobutene ring, other than polycyclic polyenes having two reactive double bonds in a fused ring system; (b) at least one polycyclic polyene having at least two chemically distinguishable non-aromatic, non-conjugated carbon-carbon double bonds in its rings; (c) at least one cyclic polysiloxane containing three or more .tbd.SiH groups.
Inventors
- 👤 John K. Bard
- 👤 Julia S. Burnier
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-06 20:18
CPC Classifications
C; C08; C08G; C08G77/00; C08G77/48; C08G77/50; C08J; C08J5/00; C08J5/24; C08J5/241; C08J5/244; C08J5/249; C08L; C08L83/00; C08L83/14; C08J2383/00; C08J2383/04; H; H05; H05K; H05K1/00; H05K1/02; H05K1/03; H05K1/0313; H05K1/032
Claims Analysis
Total Claims: 20
Claim 1
Independent Claim
156 words
A crosslinkable organosilicon prepolymer or crosslinked organosilicon polymer comprising alternating hydrocarbon and cyclic polysiloxane residues, which is the hydrosilation reaction product of: (a) at least one polyene having at least two non-aromatic, non-conjugated carbon-carbon double bonds highly reactive in hydrosilation, the carbon-carbon double bonds being either in an alpha, beta or gamma position on a linear carbon moiety, next to two bridgehead positions in a strained polycyclic aliphatic ring structure, or in a cyclobutene ring, other than polycyclic polyenes having two reactive double bonds in a fused ring system; (b) at least one polycyclic polyene having at least two chemically distinguishable non-aromatic, non-conjugated carbon-carbon double bonds in its rings wherein the at least two carbon-carbon double bonds have highly different rates of reaction in hydrosilation and one of the carbon-carbon double bonds will react prior to substantial reaction of the other carbon-carbon double bond(s); (c) at least one cyclic polysiloxane containing three or more .tbd.SiH groups.
Claim 2
Dependent Claim
156 words
A crosslinkable organosilicon prepolymer or crosslinked organosilicon polymer comprising alternating hydrocarbon and cyclic polysiloxane residues, which is the hydrosilation reaction product of: (a) at least one polyene having at least two non-aromatic, non-conjugated carbon-carbon double bonds highly reactive in hydrosilation, the carbon-carbon double bonds being either in an alpha, beta or gamma position on a linear carbon moiety, next to two bridgehead positions in a strained polycyclic aliphatic ring structure, or in a cyclobutene ring, other than polycyclic polyenes having two reactive double bonds in a fused ring system; (b) at least one polycyclic polyene having at least two chemically distinguishable non-aromatic, non-conjugated carbon-carbon double bonds in its rings wherein the at least two carbon-carbon double bonds have highly different rates of reaction in hydrosilation and one of the carbon-carbon double bonds will react prior to substantial reaction of the other carbon-carbon double bond(s); (c) at least one cyclic polysiloxane containing three or more .tbd.SiH groups.
Claim 3
Dependent Claim
105 words
The polymer or prepolymer of claim 1 wherein polyene (a) is a monomer having two non-aromatic, non-conjugated carbon-carbon double bonds highly reactive in hydrosilation of the following general formulae: R.sub.1 -R.sub.2 -R.sub.3 (I) or R.sub.1 -R.sub.3 (II) where R 1 and R 3 are selected from the group consisting of vinyl, propenyl, butenyl, isopropenyl and norbornenyl; and R 2 is selected from the group consisting of aliphatic, cycloaliphatic, aromatic, alkoxy, aryloxy, and siloxy radicals, and esters, amides, sulfones, sulfoxides, ketones and ethers; having a total molecular weight of less than 1,000; wherein in formula (II) only one of R 1 and R 3 is norbornenyl.
Claim 4
Dependent Claim
32 words
The polymer or prepolymer of claim 2 wherein R 2 is selected from the group consisting of substituted or unsubstituted alkyl, alkoxy, aryl, aryloxy, siloxy, ester, amide, sulfone, sulfoxide, ketone and ether.
Claim 5
Dependent Claim
40 words
The polymer or prepolymer of claim 1 wherein polyene (a) has the general formula: ##STR4## wherein R 2 is selected from the group consisting of substituted or unsubstituted alkyl, alkoxy, aryl, aryloxy, siloxy, ester, amide, sulfone, sulfoxide, ketone and ether.
Claim 6
Dependent Claim
18 words
The polymer or prepolymer of claim 2 wherein polyene (a) has a total molecular weight less than 500.
Claim 7
Dependent Claim
18 words
The polymer or prepolymer of claim 4 wherein polyene (a) has a total molecular weight less than 500.
Claim 8
Dependent Claim
79 words
The crosslinked polymer of claim 1 wherein the polycyclic polyene (b) has two non-aromatic, non-conjugated carbon-carbon double bonds and (i) one of the non-aromatic, non-conjugated carbon-carbon double bonds is next to two bridgehead positions in a strained polycyclic aliphatic ring or in a cyclobutene ring and (ii) the other non-aromatic, non-conjugated carbon-carbon double bond is 1,2 disubstituted and is not next to two bridgehead positions in a strained polycyclic aliphatic ring structure and is not in a cyclobutene ring.
Claim 9
Dependent Claim
80 words
The crosslinked polymer of claim 2 wherein in the polycyclic polyene (b) has two non-aromatic, non-conjugated carbon-carbon double bonds and (i) one of the non-aromatic, non-conjugated carbon-carbon double bonds is next to two bridgehead positions in a strained polycyclic aliphatic ring or in a cyclobutene ring and (ii) the other non-aromatic, non-conjugated carbon-carbon double bond is 1,2 disubstituted and is not next to two bridgehead positions in a strained polycyclic aliphatic ring structure and is not in a cyclobutene ring.
Claim 10
Dependent Claim
25 words
The polymer or prepolymer of claim 1 wherein the polycyclic polyene (b) has the general formula: ##STR5## wherein n is 0, 1, 2 or 3.
Claim 11
Dependent Claim
13 words
The polymer or prepolymer of claim 1 wherein polycyclic polyene (b) is dicyclopentadiene.
Claim 12
Dependent Claim
62 words
The polymer of prepolymer of claim 1 wherein the cyclic polysiloxane (c) has the general formula: ##STR6## wherein R is hydrogen, a saturated, substituted or unsubstituted alkyl or alkoxy radical, a substituted or unsubstituted aromatic or aryloxy radical, n is an integer from 3 to about 20, and R is hydrogen on at least three of the silicon atoms in the molecule.
Claim 13
Dependent Claim
35 words
The polymer or prepolymer of claim 1 wherein the cyclic polysiloxane (c) is selected from the group consisting of tetra- and penta-methylcyclotetrasiloxanes, tetra-, penta- and hexa-methylcyclopentasiloxane, tetra-, penta- and hexa-methylcyclohexasiloxane, tetraethyl cyclotetrasiloxane and tetraphenyl cyclotetrasiloxane.
Claim 14
Dependent Claim
35 words
The polymer or prepolymer of claim 9 wherein the cyclic polysiloxane (c) is selected from the group consisting of tetra- and penta-methylcyclotetrasiloxanes, tetra-, penta- and hexa-methylcyclopentasiloxane, tetra-, penta- and hexa-methylcyclohexasiloxane, tetraethyl cyclotetrasiloxane and tetraphenyl cyclotetrasiloxane.
Claim 15
Dependent Claim
30 words
The polymer or prepolymer of claim 1 wherein the cyclic polysiloxane (c) is selected from the group consisting of tetra- and penta-methylcyclotetrasiloxanes, tetra-, penta- and hexa-methylcyclopentasiloxane, tetra-, penta- and hexa-methylcyclohexasiloxane.
Claim 16
Dependent Claim
31 words
The polymer or prepolymer of claim 1 wherein polyene (a) and polycyclic polyene (b) each have only two carbon-carbon double bonds, both of which are reactive in hydrosilation and wherein: ##EQU4##
Claim 17
Dependent Claim
9 words
The polymer or prepolymer of claim 15 wherein: ##EQU5##
Claim 18
Dependent Claim
41 words
The polymer of prepolymer of claim 15 wherein polyene (a) is 5-vinyl-2-norbornene and polycyclic polyene (b) is dicyclopentadiene, and the ratio of double bonds in (a) and (b) to SiH bonds in (c) is in the range of 1.1:1 to 1.2:1.
Claim 19
Dependent Claim
10 words
The polymer of claim 1 which is reinforced with fibers.
Claim 20
Dependent Claim
21 words
A prepolymer as claimed in claim 1 having 30 to 75% of the SiH groups of the cyclic polysiloxane (c) reacted.
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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) | 1994-11-25 | 1995-05-27 | 1995-11-26 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1998-11-25 | 1999-05-27 | 1999-11-26 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 2002-11-25 | 2003-05-27 | 2003-11-26 | $7700.00 | Window Closed / Lapsed |