Patent US3613724A successfully refreshed from Google Patents.
Patent US4816498A successfully refreshed from Google Patents.
US4816498A
Expired / Lapsed
US
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Ethers of oligomeric phenol-dialdehyde condensation products and a vinyl-benzyl compound
Assignee: Isola Laminate Systems Corp
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Filing: 1987-11-30
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Granted: 1989-03-28
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Expires: 2007-11-30
Abstract
Abstract Oligomeric condensation products of certain dialdehydes and phenols can be end-capped with a vinylbenzyl moiety and certain other moieties, especially alkyl groups, to afford thermosetting resins particularly valuable in making laminated circuit boards. Resins prepared by the reaction of 1 molar proportion of glyoxal with from 3 to 4 molar proportions of phenol and end-capped with from 50 to 85% vinylbenzyl groups with the remainder being alkyls of 1 through 11 carbon atoms are particularly useful.
Inventors
- 👤 Joseph J. Zupancic
- 👤 Jean M. J. Frechet
- 👤 Andrew M. Zweig
- 👤 Jeffery P. Conrad
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-09 22:43
CPC Classifications
C; C08; C08G; C08G8/00; C08G8/28; C08G8/36; H; H01; H01B; H01B3/00; H01B3/18; H01B3/30; H01B3/44; H05; H05K; H05K1/00; H05K1/02; H05K1/03; H05K1/0313; H05K1/032; H05K1/0326
Claims Analysis
Total Claims: 36
Claim 1
Independent Claim
158 words
A thermosetting resin of an ether of the oligomeric condensation product of: (a) 1 molar proportion of a dialdehyde; and (b) from about 3 to about 4 molar proportions of a phenol; where the dialdehyde is selected from the group consisting of OHC(CH 2 ) n CHO, where n=0 or an integer from 1 to 6, cyclopentanedialdehyde, phthalaldehyde, isophthalaldehyde, terephthalaldehyde, hexahydrophthalaldehyde, cycloheptanedialdehyde, hexahydroisophthalaldehyde, hexahydroterephthalaldehyde, and cyclooctanedialdehyde; where the phenol has the structure R 1 C 6 H 4 OH where R 1 is hydrogen or an alkyl group containing from 1 to about 10 carbon atoms; and where the phenol residue of said oligomeric condensation product is etherified with one or more substituents to afford ether moieties randomly selected from the group consisting of vinylbenzyl, alkyl moieties containing from 1 to 10 carbon atoms, cycloalkyl moieties of 5 to 10 carbon atoms, and benzyl, with the ratio of vinylbenzyl to other moieties being from 1:1 to about 6:1.
Claim 2
Dependent Claim
158 words
A thermosetting resin of an ether of the oligomeric condensation product of: (a) 1 molar proportion of a dialdehyde; and (b) from about 3 to about 4 molar proportions of a phenol; where the dialdehyde is selected from the group consisting of OHC(CH 2 ) n CHO, where n=0 or an integer from 1 to 6, cyclopentanedialdehyde, phthalaldehyde, isophthalaldehyde, terephthalaldehyde, hexahydrophthalaldehyde, cycloheptanedialdehyde, hexahydroisophthalaldehyde, hexahydroterephthalaldehyde, and cyclooctanedialdehyde; where the phenol has the structure R 1 C 6 H 4 OH where R 1 is hydrogen or an alkyl group containing from 1 to about 10 carbon atoms; and where the phenol residue of said oligomeric condensation product is etherified with one or more substituents to afford ether moieties randomly selected from the group consisting of vinylbenzyl, alkyl moieties containing from 1 to 10 carbon atoms, cycloalkyl moieties of 5 to 10 carbon atoms, and benzyl, with the ratio of vinylbenzyl to other moieties being from 1:1 to about 6:1.
Claim 3
Dependent Claim
25 words
The resin of claim 1 where the dialdehyde is OHC(CH 2 ) n CHO and n is 0 or an integer from 1 to 4.
Claim 4
Dependent Claim
9 words
The resin of claim 2 where n is zero.
Claim 5
Dependent Claim
10 words
The resin of claim 1 where the phenol is phenol.
Claim 6
Dependent Claim
10 words
The resin of claim 1 where the phenol is cresol.
Claim 7
Dependent Claim
24 words
The resin of claim 1 further characterized in that each oligomeric condensation product has from about 4 to about 60 phenol moietes per molecule.
Claim 8
Dependent Claim
19 words
The resin of claim 6 where the condensation product has from 4 to about 22 phenolic moieties per molecule.
Claim 9
Dependent Claim
26 words
The resin of claim 7 further characterized in that the oligomeric condensation product has an average from about 5 to about 8 phenolic moieties per molecule.
Claim 10
Dependent Claim
30 words
The resin of claim 4 where the dialdehyde is glyoxal and further characterized in that the molecular weight of each oligomeric condensation product is from about 400 to about 6000.
Claim 11
Dependent Claim
21 words
The resin of claim 9 where the molecular weight of each oligomeric condensation product is from about 400 to about 2200.
Claim 12
Dependent Claim
25 words
The resin of claim 9 further characterized in that the average molecular weight of the oligomeric condensation product is from about 500 to about 800.
Claim 13
Dependent Claim
27 words
The resin of claim 1 further characterized in that each aromatic ring of the oligomeric condensation product has from 1 to about 3 bromine or chlorine atoms.
Claim 14
Dependent Claim
30 words
The resin of claim 12 where the dialdehyde is glyoxal and the phenol is phenol, and where each aromatic ring has from 1 to about 3 bromine or chlorine atoms.
Claim 15
Dependent Claim
26 words
The resin of claim 1 where the other ether moieties are selected from the group consisting of alkyl moieties having 1 through about 4 carbon atoms.
Claim 16
Dependent Claim
14 words
The resin of claim 1 where the alkyl moiety is a primary alkyl moiety.
Claim 17
Dependent Claim
159 words
A mixture of thermosetting resins of ethers of the oligomeric condensation products of: (a) 1 molar proportion of a dialdehyde; and (b) from about 3 to about 4 molar proportions of a phenol; where the dialdehyde is selected from the group consisting of OHC(CH 2 ) n CHO, where n=0 or an integer from 1 to 6, cyclopentanedialdehyde, phthalaldehyde, isophthalaldehyde, terephthalaldehyde, hexahydrophthalaldehyde, cycloheptanedialdehyde, hexahydroisophthalaldehyde, hexahydroterephthalaldehyde, and cyclooctanedialdehyde, where the phenol has the structure R 1 C 6 H 4 OH where R 1 is hydrogen or an alkyl group containing from 1 to about 10 carbon atoms; and wherein the phenol residue of said oligomeric condensation product is etherified with one or more substituents to afford ether moieties randomly selected from the group consisting of vinylbenzyl, alkyl moieties containing from 1 to 10 carbon atoms, cycloalkyl moieties of 5 to 10 carbon atoms, and benzyl, with the ratio of vinylbenzyl to other moieties being from 1:1 to about 6:1.
Claim 18
Dependent Claim
159 words
A mixture of thermosetting resins of ethers of the oligomeric condensation products of: (a) 1 molar proportion of a dialdehyde; and (b) from about 3 to about 4 molar proportions of a phenol; where the dialdehyde is selected from the group consisting of OHC(CH 2 ) n CHO, where n=0 or an integer from 1 to 6, cyclopentanedialdehyde, phthalaldehyde, isophthalaldehyde, terephthalaldehyde, hexahydrophthalaldehyde, cycloheptanedialdehyde, hexahydroisophthalaldehyde, hexahydroterephthalaldehyde, and cyclooctanedialdehyde, where the phenol has the structure R 1 C 6 H 4 OH where R 1 is hydrogen or an alkyl group containing from 1 to about 10 carbon atoms; and wherein the phenol residue of said oligomeric condensation product is etherified with one or more substituents to afford ether moieties randomly selected from the group consisting of vinylbenzyl, alkyl moieties containing from 1 to 10 carbon atoms, cycloalkyl moieties of 5 to 10 carbon atoms, and benzyl, with the ratio of vinylbenzyl to other moieties being from 1:1 to about 6:1.
Claim 19
Dependent Claim
25 words
The mixture of claim 16 where the dialdehyde is OHC(CH 2 ) n CHO and n is 0 or an integer from 1 to 4.
Claim 20
Dependent Claim
9 words
The mixture of claim 17 where n is zero.
Claim 21
Dependent Claim
10 words
The mixture of claim 16 where the phenol is phenol.
Claim 22
Dependent Claim
10 words
The mixture of claim 16 where the phenol is cresol.
Claim 23
Dependent Claim
24 words
The mixture of claim 16 further characterized in that each oligomeric condensation product has from about 4 to about 60 phenolic moieties per molecule.
Claim 24
Dependent Claim
19 words
The mixture of claim 21 where the condensation product has from 4 to about 22 phenolic moieties per molecule.
Claim 25
Dependent Claim
21 words
The mixture of claim 22 further characterized by having an average from about 5 to about 8 phenolic moieties per molecule.
Claim 26
Dependent Claim
30 words
The mixture of claim 19 where the dialdehyde is glyoxal and further characterized in that the molecular weight of each oligomeric condensation product is from about 400 to about 6000.
Claim 27
Dependent Claim
21 words
The mixture of claim 24 where the molecular weight of each oligomeric condensation product is from about 400 to about 2200.
Claim 28
Dependent Claim
23 words
The mixture of claim 24 further characterized by the condensation product having an average molecular weight of from about 500 to about 800.
Claim 29
Dependent Claim
27 words
The mixture of claim 16 further characterized in that each aromatic ring of the oligomeric condensation products has from 1 to about 3 bromine or chlorine atoms.
Claim 30
Dependent Claim
30 words
The mixture of claim 27 where the dialdehyde is glyoxal and the phenol is phenol, and where each aromatic ring has from 1 to about 3 bromine or chlorine atoms.
Claim 31
Dependent Claim
26 words
The mixture of claim 16 where the other ether moieties are selected from the group consisting of alkyl moieties having 1 through about 4 carbon atoms.
Claim 32
Dependent Claim
14 words
The mixture of claim 16 were the alkyl moiety is a primary alkyl moiety.
Claim 33
Dependent Claim
12 words
The polymer resulting from curing the mixture of resins of claim 16.
Claim 34
Dependent Claim
10 words
The polymer of claim 31 where curing is done thermally.
Claim 35
Dependent Claim
10 words
The polymer of claim 31 where curing is performed photochemically.
Claim 36
Dependent Claim
19 words
The polymer of claim 31 where the resin has been cured with the aid of a free radical initiator.
References Cited (Backward Citations)
US4448952A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1992-03-27 | 1992-09-26 | 1993-03-28 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1996-03-27 | 1996-09-26 | 1997-03-28 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 2000-03-27 | 2000-09-26 | 2001-03-28 | $7700.00 | Window Closed / Lapsed |