Patent US5468686A successfully refreshed from Google Patents.
Patent US4500690A successfully refreshed from Google Patents.
US4500690A
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US
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Thermosetting polymers from aromatic aldehydes, azines and isopropenyl phenols
Assignee: Dow Chemical Co
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Filing: 1984-05-11
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Granted: 1985-02-19
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Expires: 2004-05-11
Abstract
Abstract Heat resistant thermosetting prepolymers are prepared by reacting one or more methylated pyridines or pyrazines with one or more aromatic dialdehydes, and isopropenyl phenols. The prepolymers can be further reacted with bismaleimides to make prepolymers with lower cure temperatures and faster cure rates. The total number of methyl groups on the pyridine or pyrazine can vary from 2 to 4. The prepolymers are cured to produce heat resistant polymers and laminates with conventional fibers such as carbon fibers.
Inventors
- 👤 Randy J. LaTulip
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-08 00:16
CPC Classifications
C; C08; C08G; C08G16/00; C08G16/02; C08G16/025; C08G16/0268; C08G16/04; C08J; C08J5/00; C08J5/24; C08J5/241; C08J5/244; C08J2361/00
Claims Analysis
Total Claims: 12
Claim 1
Independent Claim
106 words
A thermosetting prepolymer which comprises the resinous reaction product of (A) one or more aromatic dialdehydes, (B) one or more azine compounds having the formula ##STR5## where Z is N, C--CH 3 , or C--CH 2 --CH 3 , or C--H R is hydrogen, methyl, or ethyl, whereby the total number of methyl groups substituted on the ring is in the range from 2-4, and (C) a member of the group consisting of (1) monomeric para or meta ispropenyl phenols having the formula ##STR6## wherein R 1 is hydrogen, or a group inert to the polymerization reaction, (2) dimers of said phenols, and (3) mixtures thereof.
Claim 2
Dependent Claim
106 words
A thermosetting prepolymer which comprises the resinous reaction product of (A) one or more aromatic dialdehydes, (B) one or more azine compounds having the formula ##STR5## where Z is N, C--CH 3 , or C--CH 2 --CH 3 , or C--H R is hydrogen, methyl, or ethyl, whereby the total number of methyl groups substituted on the ring is in the range from 2-4, and (C) a member of the group consisting of (1) monomeric para or meta ispropenyl phenols having the formula ##STR6## wherein R 1 is hydrogen, or a group inert to the polymerization reaction, (2) dimers of said phenols, and (3) mixtures thereof.
Claim 3
Dependent Claim
18 words
The prepolymer of claim 1 wherein said azine compound is 2,4,6-trimethyl pyridine, 2,6-dimethyl pyridine, or a mixture thereof.
Claim 4
Dependent Claim
18 words
The prepolymer of claim 1 wherein said azine compound is 2,5-dimethyl pyrazine, 2,3,5,6-tetramethyl pyrazine, or a mixture thereof.
Claim 5
Dependent Claim
57 words
The prepolymer of claim 1 wherein said dialdehyde has the formula ##STR7## wherein X is independently hydrogen, chlorine, bromine, fluorine, or a monovalent hydrocarbon radical such as an alkyl group of 1-4 carbons, an aryl group of 6-8 carbons such as phenyl, tolyl, xylyl, an oxyalkyl group of 1-4 carbons or an oxyaryl group of 6-8 carbons.
Claim 6
Dependent Claim
87 words
The thermosetting prepolymer which comprises the product of claim 1 further reacted with a bismaleimide compound having the formula ##STR8## where Z is a divalent organic radical having at least two carbon atoms and selected from the group consisting of aliphatic groups, alicyclic groups, aromatic groups and groups having at least two aryl residues or cyclohexyl residues bonded together by methylene, sulfonyl, or oxygen linkages or combinations thereof and X is independently hydrogen, halogen, an alkyl group of 1-4 carbons or an aryl group of 6-8 carbons.
Claim 7
Dependent Claim
25 words
A cured composite which comprises the product obtained by heat curing the product of claims 1, 2, 3, 4, or 5 with heat resistant fibers.
Claim 8
Dependent Claim
33 words
The cured composite of claim 6 wherein the heat curing is conducted at a temperature in the range from about 150° to about 300° C. for a time sufficient to obtain a cure.
Claim 9
Dependent Claim
23 words
A thermosetting prepolymer which comprises the resinous reaction product of (A) terephthalaldehyde, (B) 2,4,6-trimethyl pyridine, and (C) p-isopropenyl phenol or a dimer thereof.
Claim 10
Dependent Claim
23 words
A thermosetting prepolymer which comprises the resinous reaction product of (A) terephthalaldehyde, (B) 2,4,6-trimethyl pyridine, and (C) p-isopropenyl phenol or a dimer thereof.
Claim 11
Dependent Claim
10 words
The prepolymer of claim 8 further reacted with N,N'-methylenedi-p-phenylene bismaleimide.
Claim 12
Dependent Claim
19 words
A cured composite which comprises the product obtained by curing the prepolymer of claim 9 with heat resistant fibers.
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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) | 1988-02-19 | 1988-08-20 | 1989-02-19 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1992-02-19 | 1992-08-20 | 1993-02-19 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1996-02-19 | 1996-08-20 | 1997-02-19 | $7700.00 | Window Closed / Lapsed |