US5141970A
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US
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Method of forming high-temperature resistant polymers
Assignee: Henkel Loctite Ireland Ltd
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Filing: 1990-12-10
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Granted: 1992-08-25
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Expires: 2010-12-10
Abstract
Abstract A method of forming high-temperature resistant polymers by a 2 step curing process comprising (a) curing a polymerizable composition at least one aromatic compound having alpha and/or beta instruction which is not substantially reactive under the curing condition of step a, particularly allyl or properyl, and (b) heating the cured composition of step a in the presence of acid to form a crosslinked resin.
Inventors
- 👤 Ciaran B. McArdle
- 👤 Joseph Burke
- 👤 John G. Woods
- 👤 II Edward K. Welch
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-03 18:08
CPC Classifications
C; C08; C08F; C08F16/00; C08F16/12; C08F16/32; C08F12/00; C08F12/02; C08F12/04; C08F12/14; C08F12/22; C08F12/24; C08F12/34; C08F16/14; C08F16/16; C08F16/22
Claims Analysis
Total Claims: 24
Claim 1
Independent Claim
531 words
A method of forming high-temperature resistant polymers said method comprising the steps of (a) curing a polymerisable composition (A) containing at least one compound of the formula VI: ##STR24## wherein is a single or multiple aromatic ring structure, each R a , which may be the same or different, is H or alkenyl, which may optionally be substituted; each R b , which may be the same or different, is alkenyl, which may optionally be substituted, each R c , which may be the same or different, is a polymerisable or non-polymerisable group which does not interfere with the polymerisation of the composition; n=1-3; m=0-3; ≦ (m+n)≦6; 0≦s≦r-(m+n) where r is the total number of substitutable positions on the ring structure: provided that (I) when the polymerisable composition A comprises a compound of formula VI and a matrix monomer, said matrix monomer being curable or polymerisable under the curing conditions of step (a), then (i) at least two of the moieties R a and/or R b must have unsaturation at the alpha or beta carbon atom or (ii) at least one of the moieties R a , R b or R c is polymerisable or curable under the curing conditions of step (a) and at least one other of R a or R b has unsaturation at the alpha or beta carbon atoms; and (II) when the polymerisable composition A comprises a mixture of compounds of formula VI then (i) at least one of said compounds has at least one moiety R a , R b or R c which is polymerisable or curable under the curing conditions of step (a) and at least one moiety R a or R b which has unsaturation at the alpha or beta carbon atom and (ii) the other compound has the same requirements as I (i) or II (i) above; and (III) when the polymerisable composition A contains as the only polymerisable component, a compound of formula VI, then said compound has at least one moiety R a , R b and/or R c which is polymerisable or curable under the curing conditions of step (a) and at least one moiety R a and R b which has unsaturation at the alpha or beta carbon atom; and provided that the curing conditions for step (a) are not such as would cause the substantial polymerisation of the moieties R a and R b having alpha or beta unsaturation, and provided that when m═0 or when the required number of moieties R a and R b having alpha or beta unsaturation is greater than the number of R b moieties having said alpha or beta unsaturation, then at least one position ortho to each --OR a (R a not equal to H) or the para position thereto, or in the case of a fused ring structure at least one substitutable position on the fused ring, is unsubstituted; the alpha carbon atom being that carbon atom nearest the oxygen atom (in the case of R a ) or the ring (in the case of R b ); and (b) subsequently heating the cured composition in the presence of acid to form a high temperature resistant crosslinked resin.
Claim 2
Independent Claim
531 words
A method of forming high-temperature resistant polymers said method comprising the steps of (a) curing a polymerisable composition (A) containing at least one compound of the formula VI: ##STR24## wherein is a single or multiple aromatic ring structure, each R a , which may be the same or different, is H or alkenyl, which may optionally be substituted; each R b , which may be the same or different, is alkenyl, which may optionally be substituted, each R c , which may be the same or different, is a polymerisable or non-polymerisable group which does not interfere with the polymerisation of the composition; n=1-3; m=0-3; ≦ (m+n)≦6; 0≦s≦r-(m+n) where r is the total number of substitutable positions on the ring structure: provided that (I) when the polymerisable composition A comprises a compound of formula VI and a matrix monomer, said matrix monomer being curable or polymerisable under the curing conditions of step (a), then (i) at least two of the moieties R a and/or R b must have unsaturation at the alpha or beta carbon atom or (ii) at least one of the moieties R a , R b or R c is polymerisable or curable under the curing conditions of step (a) and at least one other of R a or R b has unsaturation at the alpha or beta carbon atoms; and (II) when the polymerisable composition A comprises a mixture of compounds of formula VI then (i) at least one of said compounds has at least one moiety R a , R b or R c which is polymerisable or curable under the curing conditions of step (a) and at least one moiety R a or R b which has unsaturation at the alpha or beta carbon atom and (ii) the other compound has the same requirements as I (i) or II (i) above; and (III) when the polymerisable composition A contains as the only polymerisable component, a compound of formula VI, then said compound has at least one moiety R a , R b and/or R c which is polymerisable or curable under the curing conditions of step (a) and at least one moiety R a and R b which has unsaturation at the alpha or beta carbon atom; and provided that the curing conditions for step (a) are not such as would cause the substantial polymerisation of the moieties R a and R b having alpha or beta unsaturation, and provided that when m═0 or when the required number of moieties R a and R b having alpha or beta unsaturation is greater than the number of R b moieties having said alpha or beta unsaturation, then at least one position ortho to each --OR a (R a not equal to H) or the para position thereto, or in the case of a fused ring structure at least one substitutable position on the fused ring, is unsubstituted; the alpha carbon atom being that carbon atom nearest the oxygen atom (in the case of R a ) or the ring (in the case of R b ); and (b) subsequently heating the cured composition in the presence of acid to form a high temperature resistant crosslinked resin.
Claim 3
Dependent Claim
84 words
A method according to claim 1 wherein the polymerisable composition contains one or more compounds of the formula VIII: ##STR25## wherein R 1 and R 2 are H, or one of R 1 and R 2 is H and the other is methyl; R 3 and R 4 are H, lower alkyl or alkoxy if R 2 is not methyl, provided that at least one of R 3 or R 4 is H; and R 9 is selected from the group consisting of ##STR26##
Claim 4
Dependent Claim
34 words
A method according to claim 1 wherein the ring structure is selected from phenyl, fused aromatic ring structure and ##STR27## wherein R d represents a covalent bond, a substituted or unsubstituted alkylene group, ##STR28##
Claim 5
Dependent Claim
59 words
A method according to claim 1 wherein each R 1 or R b is independently selected from H (in the case of R a ), C 2 -C 10 straight or branched chain alkenyl groups or C 2 -C 10 straight or branched chain alkenyl groups interrupted by an oxygen or sulfur atom or substituted with a halo group.
Claim 6
Dependent Claim
20 words
A method according to claim 1 wherein the polymerisable composition comprises a compound of formula VI and a matrix monomer.
Claim 7
Dependent Claim
25 words
A method according to claim 5 wherein the matrix monomer is co-polymerizable with the compound of formula VI curing under the condition of step (a).
Claim 8
Dependent Claim
26 words
A method according to claim 5 wherein the matrix monomer is concurrently polymerizable with the compound of formula VI under the curing conditions of step (a).
Claim 9
Dependent Claim
21 words
A method according to claim 5 wherein the compound of formula VI is non-polymerizable under the curing condition of step (a).
Claim 10
Dependent Claim
18 words
A method according to claim 1 wherein the polymerisable composition comprises a mixture of compounds of formula VI.
Claim 11
Dependent Claim
21 words
A method according to claim 1 wherein the polymerisable composition contains as the only polymerisable component a compound of formula VI.
Claim 12
Dependent Claim
8 words
A method according to claim 1 wherein m═0.
Claim 13
Dependent Claim
15 words
A method according to claim 11 wherein s≧1 and R c is a polymerisable group.
Claim 14
Dependent Claim
64 words
A method according to claim 1 wherein R a or R b is selected from the group consisting of ##STR29## wherein R 10 , R 11 , R 12 and R 13 which may be the same or different, are H or C 1 -C 5 alkyl and at least one of R 11 , R 12 and R 13 is other than H.
Claim 15
Dependent Claim
54 words
A method according to claim 1 wherein R c is a polymerisable group selected from the group consisting of ##STR30## wherein R 1 and R 2 are H, or one of R 1 and R 2 is H and the other is methyl; a vinyl ether group; an acrylic group; or an epoxy group.
Claim 16
Dependent Claim
27 words
A method according to claim 1 wherein the curing process of step (a) is selected from radical, cationic, heat, redox, anionic, atmospheric, e-beam, X-ray, gamma-ray curing modalities.
Claim 17
Dependent Claim
24 words
A method according to claim 15 wherein the first stage of the curing process is by photocuring and the composition contains a cationic photoinitiator.
Claim 18
Dependent Claim
30 words
A method according to claim 16 wherein the polymerisable composition comprises (a) a compound of the formula VI, (b) a divinyl ether of a polyalkylene oxide, and (c) a photoinitiator.
Claim 19
Dependent Claim
30 words
A method according to claim 16 wherein the compound of formula VI is produced in situ in the composition during photocuring by cleavage beyond a phenolic oxygen or by rearrangement.
Claim 20
Dependent Claim
26 words
A method according to claim 16 wherein the second step of the curing process is carried out in the presence of acid generated by the photoinitiator.
Claim 21
Dependent Claim
28 words
A method according to claim 1 wherein the polymerisable composition contains a compound of the formula ##STR31## wherein R 9 is selected from the group consisting of ##STR32##
Claim 22
Dependent Claim
16 words
A method according to claim 1 wherein the acid is generated or released thermally or photochemically.
Claim 23
Dependent Claim
25 words
A method according to claim 1 wherein the second step of the curing process is carried out at a temperature of at least 125° C.
Claim 24
Dependent Claim
31 words
A method according to claim 1 wherein the cured composition of step a undergoes a rearrangement under the curing condition of step (b) to form a higher temperature resistant cured composition.
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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) | 1995-08-25 | 1996-02-24 | 1996-08-25 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1999-08-25 | 2000-02-24 | 2000-08-25 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 2003-08-25 | 2004-02-24 | 2004-08-25 | $7700.00 | Window Closed / Lapsed |