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US4795827A
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Cyclobutarene ketoaniline monomeric and polymeric compositions
Assignee: Dow Chemical Co
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Filing: 1987-10-16
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Granted: 1989-01-03
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Expires: 2007-10-16
Abstract
Abstract The invention comprises cyclobutarene ketoaniline monomers and the process for preparing them. The monomers can be used to graft and/or endcap a monomer or polymer having at least 1 amino-reactive functionality. The grafted and/or endcapped monomer or polymer can subsequently be processed to prepare a highly crosslinked network. The preferred monomer has the formula: ##STR1##
Inventors
- 👤 Kenneth J. Bruza
- 👤 Robert A. Kirchhoff
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-08 21:57
CPC Classifications
C; C08; C08G; C08G61/00; C08G61/02; C08G61/04; C08G61/06; C07; C07C; C07C225/00; C07C225/22
Claims Analysis
Total Claims: 12
Claim 1
Independent Claim
131 words
A process for preparing the monomer of the formula ##STR18## wherein Ar is an aromatic moiety having one valence on each of two adjacent carbon atoms of an aromatic ring; Ar 1 is substituted or unsubstituted arylene provided Ar 1 is not a cyclobutarene; each R is independently hydrogen, a monovalent electron donating moiety or a monovalent electron withdrawing moiety; and each m and n is independently an integer of 1 or 2 comprising the steps of reacting a cyclobutarene with a nitro-substituted aromatic acid halide in the presence of a reaction catalyst capable of either accepting a pair of electrons or donating a proton during the reaction and then contacting the resulting cyclobutarene intermediate with a reducing agent at conditions sufficient to selectively reduce the nitro groups to amino groups.
Claim 2
Dependent Claim
131 words
A process for preparing the monomer of the formula ##STR18## wherein Ar is an aromatic moiety having one valence on each of two adjacent carbon atoms of an aromatic ring; Ar 1 is substituted or unsubstituted arylene provided Ar 1 is not a cyclobutarene; each R is independently hydrogen, a monovalent electron donating moiety or a monovalent electron withdrawing moiety; and each m and n is independently an integer of 1 or 2 comprising the steps of reacting a cyclobutarene with a nitro-substituted aromatic acid halide in the presence of a reaction catalyst capable of either accepting a pair of electrons or donating a proton during the reaction and then contacting the resulting cyclobutarene intermediate with a reducing agent at conditions sufficient to selectively reduce the nitro groups to amino groups.
Claim 3
Dependent Claim
38 words
The process of claim 1 wherein the acid halide has the formula: ##STR19## wherein Ar 1 is substituted or unsubstituted arylene; R 1 is a chloro, bromo, or iodo; and n is an integer of 1 or 2.
Claim 4
Dependent Claim
12 words
The process of claim 2 wherein the acid halide is 4-nitrobenzoyl chloride.
Claim 5
Dependent Claim
10 words
The process of claim 3 wherein the cyclobutarene is benzocyclobutene.
Claim 6
Dependent Claim
36 words
The process of claim 1 wherein the reaction catalyst is selected from the group consisting of a compound which functions as a Lewis acid, a strong protic acid, an organic complex of iron, and trifluoroactetic anhydride.
Claim 7
Dependent Claim
22 words
The process of claim 5 wherein the reaction catalyst is selected from the group consisting of iron (III) oxide and zinc oxide.
Claim 8
Dependent Claim
13 words
The process of claim 6 wherein the reaction catalyst is iron (III) oxide.
Claim 9
Dependent Claim
24 words
The process of claim 1 wherein the molar ratio of the cyclobutarene starting material to the acid halide is about 2:1 to about 3:1.
Claim 10
Dependent Claim
21 words
The process of claim 8 wherein the molar ratio of the cyclobutarene starting material to the acid halide is about 2:1.
Claim 11
Dependent Claim
24 words
The process of claim 9 wherein the molar ratio of the acid halide to the reaction catalyst ranges from about 100:1 to about 500:1.
Claim 12
Dependent Claim
26 words
The process of claim 10 wherein the temperature of the reaction mixture required to prepare the cyclobutarene intermediate ranges from about 135° to about 150° C.
References Cited (Backward Citations)
US4540763A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1992-01-03 | 1992-07-04 | 1993-01-03 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1996-01-03 | 1996-07-04 | 1997-01-03 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 2000-01-03 | 2000-07-04 | 2001-01-03 | $7700.00 | Window Closed / Lapsed |