US5008360A
Expired / Lapsed
US
⏱️ 0.0 years remaining
Organosilicon materials
Assignee: University of Southern Mississippi Research Foundation
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Filing: 1989-10-16
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Granted: 1991-04-16
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Expires: 2009-10-16
Abstract
Abstract This invention is directed to a prepreg which comprises fiber reinforcement impregnated with the partial hydrosilation reaction product of: (a) at least one polyene having at least two non-aromatic 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; (b) at least one polycyclic polyene having at least two chemically distinguishable non-aromatic, non-conjugated carbon-carbon double bonds in its rings; and (c) at least one cyclic polysiloxane containing three or more .tbd.SiH groups; which is substantially tack-free. This invention is also directed to a laminate which is prepared by curing one or more of the prepregs beyond their gel point, and which may be clad with conductive material, and printed circuit boards made from such laminates. In addition, this invention is directed to crosslinkable prepolymers and crosslinked polymers made from components (a), (b) and (c), wherein at least one of (a) and (b) is not an isomer of tricyclopentadiene. This invention is further directed to the processes of preparing all of the aforementioned materials.
Inventors
- 👤 John K. Bard
- 👤 Julia S. Burnier
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-06 05:54
CPC Classifications
C; C08; C08G; C08G77/00; C08G77/48; C08G77/50; C08J; C08J5/00; C08J5/04; C08J5/24; C08J5/241; C08J5/244; C08J5/249; C08L; C08L83/00; C08L83/14; H; H05; H05K; H05K1/00; H05K1/02; H05K1/03; H05K1/0313; H05K1/0353; H05K1/0366; C08J2383/00; C08J2383/04; H05K1/032
Claims Analysis
Total Claims: 29
Claim 1
Independent Claim
128 words
A prepreg which comprises fiber reinforcment impregnated with the partial hydrosilation reaction product of: (a) at least one polyene having at least two non-aromatic 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; (b) dicyclopentadiene and, optionally, one or more other 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; wherein about 55 to about 75% of the .tbd.SiH groups of the at least one cyclic polysiloxane (c) are reacted and the prepreg is substantially tack-free.
Claim 2
Dependent Claim
128 words
A prepreg which comprises fiber reinforcment impregnated with the partial hydrosilation reaction product of: (a) at least one polyene having at least two non-aromatic 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; (b) dicyclopentadiene and, optionally, one or more other 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; wherein about 55 to about 75% of the .tbd.SiH groups of the at least one cyclic polysiloxane (c) are reacted and the prepreg is substantially tack-free.
Claim 3
Dependent Claim
74 words
The prepreg of claim 1 wherein the one or more other polycyclic polyene (b) has two carbon-carbon double bonds and (i) the first double bond is next to two bridgehead positions in a strained polycyclic aliphatic ring or in a cyclobutene ring and (ii) the second 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 4
Dependent Claim
20 words
The prepreg of claim 1 wherein polyene (a) is selected from the group consisting of diallyl, divinyl and bis-norbornenyl compounds.
Claim 5
Dependent Claim
29 words
The prepreg of claim 1 wherein polyene (a) is selected from the group consisting of 5-vinyl-2-norbornene, o-, m- or p-diisopropenylbenzene, o-, m- or p-divinylbenzene, diallyl ether and diallyl benzene.
Claim 6
Dependent Claim
145 words
The prepreg of claim 1 wherein polyene (a) is selected from the group consisting of dimethanohexahydronaphthalene, and compounds having the following general formulae: ##STR4## wherein R 1 , which may be the same or different in formula (II), is selected from C(R 3 ) 2 , Si(R 3 ) 2 , Si(R 3 ) 2 --Si(R 3 ) 2 , C(R 3 ) 2 --C(R 3 ) 2 , CON(R 3 ), OC═O, C(R 3 )═N, S═O, SO 2 , O and C═O; R 2 is an aliphatic, aromatic or siloxy radical that during hydrosilation does not substantially react with SiH or carbon-carbon double bonds, or interfere with hydrosilation catalysis; R 3 is any substituent that during hydrosilation does not substantially react with SiH or carbon-carbon double bonds, or interfere with hydrosilation catalysis; and the total molecular weight of the compound is less than 500.
Claim 7
Dependent Claim
27 words
The prepreg of claim 5 wherein R 2 is selected from substituted or unsubstituted alkyl, alkoxy, aryl, aryloxy, siloxy, ester, amide, sulfone, sulfoxide, ketone, ether, or oxygen.
Claim 8
Dependent Claim
21 words
The prepreg of claim 6 wherein R 3 is selected from H; halogen; aromatic radicals; linear, cyclic or branched aliphatic radicals.
Claim 9
Dependent Claim
23 words
The prepreg of claim 6 wherein R 3 is H, Cl, Br, F or an alkyl, aryl, ester, amide, ether or ketone radical.
Claim 10
Dependent Claim
14 words
The prepreg of claim 1 wherein polyene (a) is the symmetrical isomer of tricyclopentadiene.
Claim 11
Dependent Claim
26 words
The prepreg of claim 1 wherein the one or more other polycyclic polyene (b) has the general formula: ##STR5## wherein n is 1, 2 or 3.
Claim 12
Dependent Claim
60 words
The prepreg 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
32 words
The prepreg 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
27 words
The prepreg 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 15
Dependent Claim
7 words
The prepreg of claim 1 wherein: ##EQU4##
Claim 16
Dependent Claim
7 words
The prepreg of claim 1 wherein: ##EQU5##
Claim 17
Dependent Claim
39 words
The prepreg of claim 14 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 18
Dependent Claim
49 words
The prepreg of claim 14 wherein polyene (a) is the symmetrical isomer of tricyclopentadiene and polycyclic polyene (b) comprises the unsymmetrical isomer of tricyclopentadiene and dicyclopentadiene, and the ratio of double bonds in (a) and (b) to SiH bonds in (c) is in the range of 0.8:1 to 1.2:1.
Claim 19
Dependent Claim
19 words
A laminate prepared by curing by hydrosilation at least two prepregs according to claim 1 beyond their gel point.
Claim 20
Dependent Claim
13 words
A laminate as claimed in claim 18 which is clad with conductive material.
Claim 21
Dependent Claim
15 words
A printed circuit board prepared from at least one laminate as claimed in claim 19.
Claim 22
Dependent Claim
15 words
A printed circuit board prepared from at least one prepreg as claimed in claim 1.
Claim 23
Dependent Claim
25 words
The prepreg of claim 1 wherein about 60 to about 70% of the .tbd.SiH groups of the at least one cyclic polysiloxane (c) are reacted.
Claim 24
Dependent Claim
25 words
The prepreg of claim 2 wherein about 60 to about 70% of the .tbd.SiH groups of the at least one cyclic polysiloxane (c) are reacted.
Claim 25
Dependent Claim
25 words
The prepreg of claim 14 wherein about 60 to about 70% of the .tbd.SiH groups of the at least one cyclic polysiloxane (c) are reacted.
Claim 26
Dependent Claim
15 words
The prepreg of claim 1 wherein the polyene (a) has molecular weight less than 500.
Claim 27
Dependent Claim
15 words
The prepreg of claim 2 wherein the polyene (a) has molecular weight less than 500.
Claim 28
Dependent Claim
15 words
The prepreg of claim 23 wherein the polyene (a) has molecular weight less than 500.
Claim 29
Dependent Claim
15 words
The prepreg of claim 24 wherein the polyene (a) has molecular weight less than 500.
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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) | 1994-04-15 | 1994-10-15 | 1995-04-16 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1998-04-15 | 1998-10-15 | 1999-04-16 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 2002-04-15 | 2002-10-15 | 2003-04-16 | $7700.00 | Window Closed / Lapsed |