US4578439A
Expired / Lapsed
US
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Styryl pyridine cyanates, styryl pyrazine cyanates and polymers thereof
Assignee: Dow Chemical Co
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Filing: 1984-08-09
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Granted: 1986-03-25
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Expires: 2004-08-09
Abstract
Abstract Styryl pyridine and styryl pyrazine cyanates are prepared by cyanating the reaction product of (A) a substituted pyridine and/or pyrazine with (B) a substituted aromatic aldehyde with the proviso that at least one of the components (A) or (B) contains a hydroxyl group which is susceptible to being cyanated. These cyanates can be homopolymerized or copolymerized with other materials to produce polymers having excellent high temperature resistance, good mechanical strength and excellent processability.
Inventors
- 👤 Robert E. Hefner, Jr.
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-09 14:07
CPC Classifications
C; C07; C07D; C07D213/00; C07D213/02; C07D213/04; C07D213/24; C07D213/28; C07D213/30; C08; C08G; C08G16/00; C08G16/02; C08G16/025; C08G16/0268; C08G16/04; C08G59/00; C08G59/18; C08G59/40; C08G59/4007; C08G59/4014; C08J; C08J5/00; C08J5/24; C08J5/241; C08J5/244; C08L; C08L61/00
Claims Analysis
Total Claims: 34
Claim 1
Independent Claim
208 words
A styryl pyridine cyanate or styryl pyrazine cyanate composition resulting from cyanating a product resulting from reacting (A) at least one of (1) one or more pyridine compounds represented by the formula ##STR13## (2) one or more pyrazine compounds represented by the formula ##STR14## (3) a mixture of 1 and 2; with (B) a substituted aromatic aldehyde represented by the formula ##STR15## wherein each R is independently hydrogen, hydroxyl, methyl or ethyl; each R' is independently a hydroxyl or a ##STR16## each R" is independently hydrogen, methyl or ethyl; x has a value of 3; x' has a value of 2; y has a value of 1 or 2; y' has a value of 3 or 4; the sum of y and y' has a value of 5; and with the proviso that at least one of R and R' is a hydroxyl group and wherein (i) components (A) and (B) are employed in quantities which provide the resultant reaction product with a reacted molar ratio of (B) to (A) of from about 0.33:1 to about 4:1 and (ii) at least about 1 percent of the rings in the resultant reaction product of (A) and (B) contain at least one hydroxyl group which is susceptible to being cyanated.
Claim 2
Dependent Claim
208 words
A styryl pyridine cyanate or styryl pyrazine cyanate composition resulting from cyanating a product resulting from reacting (A) at least one of (1) one or more pyridine compounds represented by the formula ##STR13## (2) one or more pyrazine compounds represented by the formula ##STR14## (3) a mixture of 1 and 2; with (B) a substituted aromatic aldehyde represented by the formula ##STR15## wherein each R is independently hydrogen, hydroxyl, methyl or ethyl; each R' is independently a hydroxyl or a ##STR16## each R" is independently hydrogen, methyl or ethyl; x has a value of 3; x' has a value of 2; y has a value of 1 or 2; y' has a value of 3 or 4; the sum of y and y' has a value of 5; and with the proviso that at least one of R and R' is a hydroxyl group and wherein (i) components (A) and (B) are employed in quantities which provide the resultant reaction product with a reacted molar ratio of (B) to (A) of from about 0.33:1 to about 4:1 and (ii) at least about 1 percent of the rings in the resultant reaction product of (A) and (B) contain at least one hydroxyl group which is susceptible to being cyanated.
Claim 3
Dependent Claim
70 words
A composition of claim 1 wherein (i) components (A) and (B) are employed in quantities which provide the resultant reaction product with a reacted molar ratio of (B) to (A) of from about 0.5:1 to about 4:1 and (ii) at least about 20 to 100 percent of the rings in the resultant reaction product of (A) and (B) contain at least one hydroxyl group which is susceptible to being cyanated.
Claim 4
Dependent Claim
71 words
A composition of claim 2 wherein (i) components (A) and (B) are employed in quantities which provide the resultant reaction product with a reacted molar ratio of (B) to (A) of from about 0.7:1 to about 3:1 and (ii) at least about 30 to about 75 percent of the rings in the resultant reaction product of (A) and (B) contain at least one hydroxyl group which is susceptible to being cyanated.
Claim 5
Dependent Claim
97 words
A composition of claim 1 wherein (i) component (A-1) is 2,3-dimethyl pyridine, 2,4-dimethyl pyridine, 2,5-dimethyl pyridine, 2,6-dimethyl pyridine, 3,4-dimethyl pyridine, 3,5-dimethyl pyridine, 3,5-dimethyl-2-ethyl pyridine, 2,3,4,6-tetramethyl pyridine, 2,3,5-trimethyl pyridine, 2,3,6-trimethyl pyridine, 2,4,5-trimethyl pyridine, 2,4,6-trimethyl pyridine, 2,4-dimethyl-6-hydroxy pyridine, 2,6-dimethyl-4-hydroxy pyridine, 2,6-dimethyl-3-hydroxy pyridine,2,4,6-trimethyl-5-hydroxy pyridine, or a mixture therof; (ii) Component (A-2) is 2,5-dimethyl pyrazine, 2,3-dimethyl pyrazine, 2,6-dimethyl pyrazine, 2,3,5-trimethyl pyrazine, 2,3,5,6-tetramethyl pyrazine, 2,5-dimethyl-6-hydroxyl pyrazine, 2,5-dimethyl-3-ethyl pyrazine, or a mixture therof; and (iii) Component (B) is 2-hydroxy benzaldehyde, 3-hydroxy benzaldehyde, 4-hydroxy benzaldehyde, 2-hydroxy-3-methyl benzaldehyde, 2-hydroxy-3-ethyl benzaldehyde, 4-hydroxy-3,5-dimethyl benzaldehyde, terephthaldehyde, 2,6-dihydroxy benzaldehyde, methyl terephthaldehydes, dimethyl terephthaldehydes, ethyl terephthaldehydes, or a mixture therof.
Claim 6
Dependent Claim
75 words
A composition of claim 2 wherein (i) component (A-1) is 2,3-dimethyl pyridine, 2,4-dimethyl pyridine, 2,5-dimethyl pyridine, 2,6-dimethyl pyridine, 3,4-dimethyl pyridine, 3,5-dimethyl pyridine, 3,5-dimethyl-2-ethyl pyridine, 2,3,4,6-tetramethyl pyridine, 2,3,5-trimethyl pyridine, 2,3,6-trimethyl pyridine, 2,4,5-trimethyl pyridine, 2,4,6-trimethyl pyridine, 2,4-dimethyl-6-hydroxy pyridine, 2,6-dimethyl-4-hydroxy pyridine, 2,6-dimethyl-3-hydroxy pyridine, 2,4,6-trimethyl-5-hydroxy pyridine, or a mixture therof; (ii) Component (B) is 2-hydroxy benzaldehyde, 3-hydroxy benzaldehyde, 4-hydroxy benzaldehyde, 2-hydroxy-3-methyl benzaldehyde, 2-hydroxy-3-ethyl benzaldehyde, 4-hydroxy-3,5-dimethyl benzaldehyde, terephthaldehyde, 2,6-dihydroxy benzaldehyde, methyl terephthaldehydes, dimethyl terephthaldehydes, ethyl terephthaldehydes, or a mixture therof.
Claim 7
Dependent Claim
24 words
A composition of claim 3 wherein (i) component (A-1) is 2,6-dimethyl pyridine, 2,4,6-trimethyl pyridine or a mixture therof; (ii) Component (B) is 4-hydroxy benzaldehyde.
Claim 8
Dependent Claim
13 words
A polymer prepared by polymerizing one or more cyanated composition of claim 1.
Claim 9
Dependent Claim
13 words
A polymer prepared by polymerizing one or more cyanated composition of claim 2.
Claim 10
Dependent Claim
13 words
A polymer prepared by polymerizing one or more cyanated composition of claim 3.
Claim 11
Dependent Claim
13 words
A polymer prepared by polymerizing one or more cyanated composition of claim 4.
Claim 12
Dependent Claim
13 words
A polymer prepared by polymerizing one or more cyanated composition of claim 5.
Claim 13
Dependent Claim
13 words
A polymer prepared by polymerizing one or more cyanated composition of claim 6.
Claim 14
Dependent Claim
138 words
A polymerizable or curable mixture of (A) at least one of the aforementioned styryl pyridine cyanates, styryl pyrazine cyanates or combination thereof of claims 1, 2, 3, 4, 5 or 6; and (B) at least one material selected from (1) (a) styryl pyridines, (b) styryl pyridine prepolymers, (c) styryl pyridine polymers or (d) any combination thereof; (2) (a) vinyl styryl pyridines, (b) vinyl styryl pyridine prepolymers, (c) vinyl styryl pyridine polymers or (d) any combinatioin thereof; (3) alkenyl phenyl cyanates; (4) (a) dicyanates, (b) polycyanates or (c) any combination thereof; (5) (a) bismaleimides, (b) polymaleimides or (c) any combination thereof; (6) epoxy resins; (7) (a) alkenyl phenol capped styryl pyridines, (b) alkenyl phenol capped styryl pyridine prepolymers, (c) alkenyl phenol capped styryl pyridine polymers or (d) any combination thereof; or (8) mixtures thereof in any proportion and combination.
Claim 15
Dependent Claim
24 words
A polymerizable or curable mixture of claim 13 wherein component (B-2) is a vinyl polystyryl pyridine prepared from 2,4,6-trimethyl pyridine, terephthaldehyde and 2-methyl-5-vinyl pyridine.
Claim 16
Dependent Claim
23 words
A polymerizable or curable mixture of claim 13 wherein (i) component (B-3) is p-isopropenylphenyl cyanate and (ii) component (B-4) is bisphenol A dicyanate.
Claim 17
Dependent Claim
18 words
A polymerizable or curable mixture of claim 13 wherein component (B-6) is a diglycidyl ether of bisphenol A.
Claim 18
Dependent Claim
13 words
A polymerizable or curable mixture of claim 13 wherein component (B-5) is N,N'-(methylenedi-p-phenylene)bismaleimide.
Claim 19
Dependent Claim
12 words
Products resulting from polymerization and/or curing of a composition of claim 13.
Claim 20
Dependent Claim
12 words
Products resulting from polymerization and/or curing of a composition of claim 14.
Claim 21
Dependent Claim
12 words
Products resulting from polymerization and/or curing of a composition of claim 15.
Claim 22
Dependent Claim
12 words
Products resulting from polymerization and/or curing of a composition of claim 16.
Claim 23
Dependent Claim
12 words
Products resulting from polymerization and/or curing of a composition of claim 17.
Claim 24
Dependent Claim
9 words
An article prepared from a polymer of claim 7.
Claim 25
Dependent Claim
9 words
An article prepared from a polymer of claim 8.
Claim 26
Dependent Claim
9 words
An article prepared from a polymer of claim 9.
Claim 27
Dependent Claim
9 words
An article prepared from a polymer of claim 10.
Claim 28
Dependent Claim
9 words
An article prepared from a polymer of claim 11.
Claim 29
Dependent Claim
9 words
An article prepared from a polymer of claim 12.
Claim 30
Dependent Claim
9 words
An article prepared from a product of claim 18.
Claim 31
Dependent Claim
9 words
An article prepared from a product of claim 19.
Claim 32
Dependent Claim
9 words
An article prepared from a product of claim 20.
Claim 33
Dependent Claim
9 words
An article prepared from a product of claim 21.
Claim 34
Dependent Claim
9 words
An article prepared from a product of claim 22.
References Cited (Backward Citations)
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1989-03-24 | 1989-09-23 | 1990-03-25 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1993-03-24 | 1993-09-23 | 1994-03-25 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1997-03-24 | 1997-09-23 | 1998-03-25 | $7700.00 | Window Closed / Lapsed |