Patent US3965125A successfully refreshed from Google Patents.
US3965125A
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Synthesis of certain bis(phthalic anhydrides)
Assignee: M&T Chemicals Inc
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Filing: 1971-02-08
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Granted: 1976-06-22
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Expires: 1991-02-08
Abstract
Abstract Monomeric high molecular weight dianhydrides or tetraacids can be produced by the nucleophilic coupling of a halo substituted phthalimides acid and an aliphatic or aromatic compound having polyfunctional groups capable of reacting with the halo moiety of the phthalinide followed by hydrolysis and dehydration. Specifically, 4-chlorophthalate sodium salt is converted to an imide to reduce side reactions with the carboxylic acid groups prior to reaction with 4,4'-disodiumdiphenylene oxide sulfone or 2,2-di (4-sodium phenoxide) propane. After the reaction of the imide and the sulfone or propane compounds, the diimide formed is converted to the corresponding dianhydride.
Inventors
- 👤 Robert A. Meyers
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-08 08:55
CPC Classifications
C; C08; C08G; C08G73/00; C08G73/06; C08G73/10; C07; C07C; C07C51/00; C07C51/54; C07C51/56; C07C63/00; C07C63/14; C07C63/15; C07D; C07D209/00; C07D209/02; C07D209/44; C07D209/48; C07D307/00; C07D307/77; C07D307/87; C07D307/89; C08L; C08L75/00
Claims Analysis
Total Claims: 7
Claim 1
Independent Claim
176 words
A method of making monomeric high molecular weight anhydrides comprising: A. i. reacting a substituted phthalimide characterized by the formula: ##SPC4## where Y is a functional group selected from the group consisting of --CL, --F, --Br, and --I, and R is selected from the group consisting of C 1 to C 5 alkyl groups, phenyl, with (ii) a polyfunctional compound characterized by the formula: A -- Z -- A wherein A is a functional group capable of reacting with Y and is selected from the group consisting of --OLi, --ONa, --OK, --SLi, --SNa, --SK, --NHC 6 H 5 , --NHCH 3 , --NHC 2 H 5 , --NHC 3 H 7 , --NHC 4 H 9 , --NHC 5 H 11 , --NHC 6 H 13 , and --NH 2 and Z is selected from the group consisting of arylene, alkylene, haloarylene, oxyhisaryl, oxlybisaryl, alkylenebisaryl, nitro substituted anthraquinonylene, azabisoryl, alkyl substituted pyrimidylene, and pyrimidylene sulfonebisaryl to form a diimide terminated cyclic intermediate, and B. hydrolyzing and subsequently dehydrating said diimide terminated intermediate to the corresponding dianhydride.
Claim 2
Independent Claim
176 words
A method of making monomeric high molecular weight anhydrides comprising: A. i. reacting a substituted phthalimide characterized by the formula: ##SPC4## where Y is a functional group selected from the group consisting of --CL, --F, --Br, and --I, and R is selected from the group consisting of C 1 to C 5 alkyl groups, phenyl, with (ii) a polyfunctional compound characterized by the formula: A -- Z -- A wherein A is a functional group capable of reacting with Y and is selected from the group consisting of --OLi, --ONa, --OK, --SLi, --SNa, --SK, --NHC 6 H 5 , --NHCH 3 , --NHC 2 H 5 , --NHC 3 H 7 , --NHC 4 H 9 , --NHC 5 H 11 , --NHC 6 H 13 , and --NH 2 and Z is selected from the group consisting of arylene, alkylene, haloarylene, oxyhisaryl, oxlybisaryl, alkylenebisaryl, nitro substituted anthraquinonylene, azabisoryl, alkyl substituted pyrimidylene, and pyrimidylene sulfonebisaryl to form a diimide terminated cyclic intermediate, and B. hydrolyzing and subsequently dehydrating said diimide terminated intermediate to the corresponding dianhydride.
Claim 3
Dependent Claim
11 words
A method according to claim 1 wherein the phthalimide is 4-chloro-N-butylphalimide.
Claim 4
Dependent Claim
13 words
A method according to claim 1 wherein the polyfunctional compound is 4,4'-disodiumdiphenyloxide sulfone.
Claim 5
Dependent Claim
14 words
A method according to claim 1 wherein the polyfunctional compound is 2,2-di(4-sodium phenoxide) propane.
Claim 6
Dependent Claim
14 words
A method according to claim 3 wherein the dianhydride product is bis-[4(3,4-dicarboxyphenoxy)phenyl] sulfone dianhydride.
Claim 7
Dependent Claim
14 words
A method according to claim 4 wherein the dianhydride product is 2,2-bis[4-(3,4-dicarboxyphenoxy)phenyl] propane dianhydride.
References Cited (Backward Citations)
US3431240A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1979-06-22 | 1979-12-22 | 1980-06-22 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1983-06-22 | 1983-12-22 | 1984-06-22 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1987-06-22 | 1987-12-22 | 1988-06-22 | $7700.00 | Window Closed / Lapsed |