US4970276A
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US
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Phenolic triazine copolymers based on pure cyanato novolacs
Assignee: Honeywell International Inc
•
Filing: 1989-05-26
•
Granted: 1990-11-13
•
Expires: 2009-05-26
Abstract
Abstract Phenolic cyanate/phenolic triazine copolymers and cured resins prepared therefrom.
Inventors
- 👤 Sajal Das
- 👤 Dusan C. Prevorsek
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-04 10:17
CPC Classifications
C; C08; C08G; C08G73/00; C08G73/06; C08G73/0622; C08G73/0638; C08G73/065; C08G73/0655; C08G8/00; C08G8/28
Claims Analysis
Total Claims: 62
Claim 1
Independent Claim
244 words
A phenolic triazine/phenolic cyanate copolymer comprising three or more phenolic moieties of the formula: ##STR8## linked by way of at least one of open valencies to one or more triazine moieties of the formula: ##STR9## and wherein the remainder of the open valencies of said phenolic moieties are substituted with --OH, --OCN, or other triazine moieties, provided that at least one of said remaining open valencies is substituted with a --OCN moiety; wherein: n is a positive whole number equal to or greater than 1; q and r are the same or different at each occurrence and are whole numbers from 0 to 3 with the proviso that the sum of q and r at each occurrence is equal to 3; o and p are the same or different at each occurrence and are whole numbers from 0 to 4, with the proviso that the sum of o and p is equal to 4; --X-- is a divalent organic radical; and R 3 is the same or different at each occurrence and is a substituent other than hydrogen which is unreactive under conditions necessary to crosslink the cyanurate moieties wherein the completely cured product of said copolymer exhibits a weight loss equal to or less than about 16 wgt. % based on the total weight of the completely cured product on heating said product from about 20° C. to a temperature of 500° C. at a rate of 10° C./min in an argon atmosphere.
Claim 2
Dependent Claim
244 words
A phenolic triazine/phenolic cyanate copolymer comprising three or more phenolic moieties of the formula: ##STR8## linked by way of at least one of open valencies to one or more triazine moieties of the formula: ##STR9## and wherein the remainder of the open valencies of said phenolic moieties are substituted with --OH, --OCN, or other triazine moieties, provided that at least one of said remaining open valencies is substituted with a --OCN moiety; wherein: n is a positive whole number equal to or greater than 1; q and r are the same or different at each occurrence and are whole numbers from 0 to 3 with the proviso that the sum of q and r at each occurrence is equal to 3; o and p are the same or different at each occurrence and are whole numbers from 0 to 4, with the proviso that the sum of o and p is equal to 4; --X-- is a divalent organic radical; and R 3 is the same or different at each occurrence and is a substituent other than hydrogen which is unreactive under conditions necessary to crosslink the cyanurate moieties wherein the completely cured product of said copolymer exhibits a weight loss equal to or less than about 16 wgt. % based on the total weight of the completely cured product on heating said product from about 20° C. to a temperature of 500° C. at a rate of 10° C./min in an argon atmosphere.
Claim 3
Dependent Claim
20 words
A copolymer according to claim 1 wherein said weight loss is equal to or greater than about 14 wgt. %.
Claim 4
Dependent Claim
20 words
A compolymer according to claim 2 wherein said weight loss is equal to or less than about 13 wgt. %.
Claim 5
Dependent Claim
60 words
A copolymer according to claim 1 wherein said completely cured product of said copolymer exhibits a weight loss equal to or less than about 6 wgt. based on the total weight of the completely cured product on heating said product from about 20° C. to a temperature of 450° C. at a rate of 10° C./min in an argon atmosphere.
Claim 6
Dependent Claim
20 words
A copolymer according to claim 4 wherein said weight loss is equal to or less than about 2.5 wgt. %.
Claim 7
Dependent Claim
56 words
A copolymer according to claim 1 wherein said completely cured product of said copolymer exhibits a % char at 1000° C. equal to or greater than about 62% based on the total weight of product on heating said product from about 20° C. to 1000° C. at a rate of 10° C./min under an argon atmosphere.
Claim 8
Dependent Claim
18 words
A copolymer according to claim 6 wherein said % char is equal to or greater than about 65%.
Claim 9
Dependent Claim
39 words
A copolymer according to claim 1 wherein up to about 30 mole % of the phenyl groups in said copolymer are substituted with triazine moieties said mole percent based on the total moles of phenyl groups in said copolymer.
Claim 10
Dependent Claim
26 words
A copolymer according to claim 8 wherein the mole % of phenyl groups substituted with triazine moieties is from about 2 to about 25 mole %.
Claim 11
Dependent Claim
39 words
A copolymer according to claim 1 wherein up to about 90 mole % of the phenyl groups in said copolymer are substituted with --OCN groups, said mole percent based on the total moles of phenyl groups in said copolymer.
Claim 12
Dependent Claim
26 words
A copolymer according to claim 10 wherein the mole % of phenyl groups substituted with --OCN groups is from about 40 to about 90 mole %.
Claim 13
Dependent Claim
39 words
A copolymer according to claim 1 wherein up to about 90 mole % of the phenyl groups of said copolymer are substituted with --OH groups, said mole % based on the total moles of phenyl groups in said copolymer.
Claim 14
Dependent Claim
26 words
A copolymer according to claim 12 wherein the mole % of phenyl groups substituted with --OH groups is from about 2 to about 50 mole %.
Claim 15
Dependent Claim
24 words
A copolymer according to claim 1 wherein the mole % of phenyl groups substituted with carbamate functions is less than about 5 mole %.
Claim 16
Dependent Claim
24 words
A copolymer according to claim 14 wherein the mole % of phenyl groups substituted with carbamate functions is less than about 2 mole %.
Claim 17
Dependent Claim
20 words
A copolymer according to claim 15 where none or substantially none of the phenyl groups are substituted with carbamate functions.
Claim 18
Dependent Claim
15 words
A copolymer according to claim 1 which comprises less than about 5 weight % dicyanamide.
Claim 19
Dependent Claim
15 words
A copolymer according to claim 17 which comprises less than about 2 weight % dicyanamide.
Claim 20
Dependent Claim
15 words
A copolymer according to claim 18 which comprises less than about 1 weight % dicyanamide.
Claim 21
Dependent Claim
14 words
A copolymer according to claim 19 which comprises no dicyanamide or substantially no dicyanamide.
Claim 22
Dependent Claim
31 words
A copolymer according to claim 1 wherein X is substituted or unsubstituted methylene or 1,4-phenyl-dimethylene, wherein permissible substituents are alkyl having from 1 to about 10 carbon atoms, halogen and furyl.
Claim 23
Dependent Claim
15 words
A copolymer according to claim 21 wherein X is a moiety of the formula: ##STR10##
Claim 24
Dependent Claim
14 words
A copolymer according to claim 1 wherein n is from 1 to about 20.
Claim 25
Dependent Claim
15 words
A copolymer according to claim 23 wherein n is from about 1 to about 10.
Claim 26
Dependent Claim
18 words
A copolymer according to claim 1 wherein: o is 0 or 1; and p is 2 or 4.
Claim 27
Dependent Claim
18 words
A copolymer according to claim 1 wherein: q is 0 or 1; and r is 2 to 3.
Claim 28
Dependent Claim
11 words
A copolymer according to claim 1 wherein R 3 is alkyl.
Claim 29
Dependent Claim
13 words
A copolymer according to claim 27 wherein R 3 is methyl or ethyl.
Claim 30
Dependent Claim
19 words
A composition comprising a copolymer phenolic resin according to claim 1 and one or more fibrous or particulate fillers.
Claim 31
Dependent Claim
13 words
A completely cured composition formed by cyclotrimerization of the copolymer of claim 1.
Claim 32
Dependent Claim
13 words
A partially cured composition formed by cyclotrimerization of the copolymer of claim 1.
Claim 33
Dependent Claim
13 words
An incompletely cured composition formed by cyclotrimerization of the copolymer of claim 1.
Claim 34
Dependent Claim
230 words
A phenolic triazine/phenolic cyanate copolymer comprising three or more phenolic moieties of the formula: ##STR11## linked by way of at least one of open valencies to one or more triazine moieties of the formula: ##STR12## and wherein the remainder of the open valencies of said phenolic moieties are substituted with --OH, --OCN, or other triazine moieties, provided that at least one of said remaining open valencies is substituted with a --OCN moiety; wherein: n is a positive whole number equal to or greater than 1; q and r are the same or different at each occurrence and are whole numbers from 0 to 3 with the proviso that the sum of q and r at each occurrence is equal to 3; o and p are the same or different at each occurrence and are whole numbers from 0 to 4, with the proviso that the sum of o and p is equal to 4; --X-- is a divalent organic radical; an R 3 is the same or different at each occurrence and is a substitutent other than hydrogen which is unreactive under conditions necessary to crosslink the cyanurate moieties: wherein said copolymer forms no or substantially no solids which are insoluble in tetrahydrofuran after storage at about a temperature of 20° C. for a time period in the range of from more than about 3 days to about 90 days.
Claim 35
Dependent Claim
230 words
A phenolic triazine/phenolic cyanate copolymer comprising three or more phenolic moieties of the formula: ##STR11## linked by way of at least one of open valencies to one or more triazine moieties of the formula: ##STR12## and wherein the remainder of the open valencies of said phenolic moieties are substituted with --OH, --OCN, or other triazine moieties, provided that at least one of said remaining open valencies is substituted with a --OCN moiety; wherein: n is a positive whole number equal to or greater than 1; q and r are the same or different at each occurrence and are whole numbers from 0 to 3 with the proviso that the sum of q and r at each occurrence is equal to 3; o and p are the same or different at each occurrence and are whole numbers from 0 to 4, with the proviso that the sum of o and p is equal to 4; --X-- is a divalent organic radical; an R 3 is the same or different at each occurrence and is a substitutent other than hydrogen which is unreactive under conditions necessary to crosslink the cyanurate moieties: wherein said copolymer forms no or substantially no solids which are insoluble in tetrahydrofuran after storage at about a temperature of 20° C. for a time period in the range of from more than about 3 days to about 90 days.
Claim 36
Dependent Claim
30 words
A copolymer according to claim 33 wherein said resin forms no or substantially no solids which are insoluble in tetrahydrofuran after storage at about 20° C. for about 90 days.
Claim 37
Dependent Claim
32 words
A copolymer according to claim 34 wherein said resin forms no or substantially no solids which are insoluble in tetrahydrofuran on storage at about 20° C. for more than about 90 days.
Claim 38
Dependent Claim
39 words
A copolymer according to claim 33 wherein up to about 30 mole % of the phenyl groups in said copolymer are substituted with triazine moieties said mole percent based on the total moles of phenyl groups in said copolymer.
Claim 39
Dependent Claim
26 words
A copolymer according to claim 36 wherein the mole % of phenyl groups substituted with triazine moieties is from about 2 to about 25 mole %.
Claim 40
Dependent Claim
39 words
A copolymer according to claim 33 wherein up to about 90 mole % of the phenyl groups in said copolymer are substituted with --OCN groups, said mole percent based on the total moles of phenyl groups in said copolymer.
Claim 41
Dependent Claim
26 words
A copolymer according to claim 38 wherein the mole % of phenyl groups substituted with --OCN groups is from about 40 to about 90 mole %.
Claim 42
Dependent Claim
38 words
A copolymer according to claim 33 wherein up to about 90 mole % of the phenyl groups of said copolymer are substituted with --OH groups, said mole based on the total moles of phenyl groups in said copolymer.
Claim 43
Dependent Claim
26 words
A copolymer according to claim 40 wherein the mole % of phenyl groups substituted with --OH groups is from about 2 to about 50 mole %.
Claim 44
Dependent Claim
24 words
A copolymer according to claim 33 wherein the mole % of phenyl groups substituted with carbamate functions is less than about 5 mole %.
Claim 45
Dependent Claim
24 words
A copolymer according to claim 42 wherein the mole % of phenyl groups substituted with carbamate functions is less than about 2 mole %.
Claim 46
Dependent Claim
20 words
A copolymer according to claim 43 where none or substantially none of the phenyl groups are substituted with carbamate functions.
Claim 47
Dependent Claim
23 words
A copolymer according to claim 33 which comprises less than about 5 weight % dicyanamide based on the total weight of the copolymer.
Claim 48
Dependent Claim
15 words
A copolymer according to claim 45 which comprises less than about 2 weight % dicyanamide.
Claim 49
Dependent Claim
15 words
A copolymer according to claim 46 which comprises less than about 1 weight % dicyanamide.
Claim 50
Dependent Claim
14 words
A copolymer according to claim 47 which comprises no dicyanamide or substantially no dicyanamide.
Claim 51
Dependent Claim
31 words
A copolymer according to claim 33 wherein X is substituted or unsubstituted methylene or 1,4-phenyl-dimethylene, wherein permissible substitutents are alkyl having from 1 to about 10 carbon atoms, halogen and furyl.
Claim 52
Dependent Claim
15 words
A copolymer according to claim 49 wherein X is a moiety of the formula: ##STR13##
Claim 53
Dependent Claim
14 words
A copolymer according to claim 33 wherein n is from 1 to about 20.
Claim 54
Dependent Claim
15 words
A copolymer according to claim 51 wherein n is from about 1 to about 10.
Claim 55
Dependent Claim
18 words
A copolymer according to claim 33 wherein: o is 0 or 1; and p is 2 or 4.
Claim 56
Dependent Claim
18 words
A copolymer according to claim 33 wherein: q is 0 or 1; and r is 2 to 3.
Claim 57
Dependent Claim
11 words
A copolymer according to claim 33 wherein R 3 is alkyl.
Claim 58
Dependent Claim
13 words
A copolymer according to claim 55 wherein R 3 is methyl or ethyl.
Claim 59
Dependent Claim
16 words
A composition comprising a copolymer phenolic resin according to claim 87 and one or more fillers.
Claim 60
Dependent Claim
13 words
A completely cured composition formed by cyclotrimerization of the copolymer of claim 33.
Claim 61
Dependent Claim
13 words
A partially cured composition formed by cyclotrimerization of the copolymer of claim 33.
Claim 62
Dependent Claim
13 words
An incompletely cured composition formed by cyclotrimerization of the copolymer of claim 33.
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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) | 1993-11-12 | 1994-05-14 | 1994-11-13 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1997-11-12 | 1998-05-14 | 1998-11-13 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 2001-11-12 | 2002-05-14 | 2002-11-13 | $7700.00 | Window Closed / Lapsed |