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EP0071749A2 Expired / Lapsed EP ⏱️ 0.0 years remaining

Novel polyimides and polyamic intermediates thereof

Assignee: Ingredion Inc
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Filing: 1982-06-29
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Granted: —
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Expires: 2002-06-29
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Abstract

Abstract Novel polyimides, optionally end-capped with polymerizable or inert groups, and the polyamic acid or ester intermediates thereof are prepared by reacting a tetracarboxylic acid compound (e.g. pyromellitic dianhydride or 3,3',4,4'-benzophenone tetracarboxylic acid dianhydride or its methyl diester) with diamines having the general formula wherein Z is oxygen or sulfur, X and/or Y are carbonyl or carbinol groups, the amine groups may be in the 2-, 3-, and/ or 4-position, and isomerism is present when X and/or Y is a carbinol group. The polyimides may be end-capped by reaction, during or after their formation, with polymerizable groups such as 3-aminophenyl acetylene or 3,6-endomethy- lene-1,2,3,6-tetrahydrophthalic anhydride. The diamines are novel classes of amines when Z is sulfur and when Z is oxygen and X, Y, or X and Y are carbinol groups.

Inventors

  • 👤 Jules E. Schoenberg
  • 👤 Stephen P. Anderson

Bibliographic Details

Application Number —
Jurisdiction EP
Data Source google_patents
Last Synchronized 2026-11-04 20:02
CPC Classifications
C; C08; C08G; C08G73/00; C08G73/06; C08G73/10; C08G73/1057; C08G73/1064; C08G73/1046; C08G73/105; Y; Y10; Y10T; Y10T428/00; Y10T428/31504; Y10T428/31721

Claims Analysis

Total Claims: 11
Claim 1
Independent Claim 180 words
A polyimide resin, comprising a chain of recurring units of the formula characterized in that A is and B is where R may be an aliphatic organic tetravalent radical containing at least two carbon atoms with no more than two carbonyl groups being attached to any one carbon atom of said tetravalent radical or where R may be a cycloaliphatic or aromatic tetravalent radical containing at least one ring with the four carbonyl groups being attached directly to separate carbon atoms in one or two rings of said radical and with each pair of carbonyl groups being attached to adjacent carbon atoms in said ring or rings of said radical; where Z is oxygen or sulfur; where X or Y or X and Y may be a carbonyl or carbinol group; where the nitrogens may be independently attached to the benzene rings in the 2-, 3-, or 4- positions; where isomerism is present when X or Y or X and Y are said carbinol groups; and where n is greater than I and equals the number of mers per molecule.
Claim 2
Dependent Claim 180 words
A polyimide resin, comprising a chain of recurring units of the formula characterized in that A is and B is where R may be an aliphatic organic tetravalent radical containing at least two carbon atoms with no more than two carbonyl groups being attached to any one carbon atom of said tetravalent radical or where R may be a cycloaliphatic or aromatic tetravalent radical containing at least one ring with the four carbonyl groups being attached directly to separate carbon atoms in one or two rings of said radical and with each pair of carbonyl groups being attached to adjacent carbon atoms in said ring or rings of said radical; where Z is oxygen or sulfur; where X or Y or X and Y may be a carbonyl or carbinol group; where the nitrogens may be independently attached to the benzene rings in the 2-, 3-, or 4- positions; where isomerism is present when X or Y or X and Y are said carbinol groups; and where n is greater than I and equals the number of mers per molecule.
Claim 3
Dependent Claim 196 words
A polyamic resin, comprising a chain of recurring units of the formula characterized in that A' is and B is where R may be an aliphatic organic tetravalent radical containing at least two carbon atoms with no more than two carbonyl groups being attached to any one carbon atom of said tetravalent radical or where R may be a cycloaliphatic or aromatic tetravalent radical containing at least one ring with the four carbonyl groups being attached directly to separate carbon atoms in one or two rings of said radical and with each pair of carbonyl groups being attached to adjacent carbon atoms in said ring or rings of said radical; where R 1 and R 2 may be hydrogen or the same or different hydrocarbon monovalent radicals; where Z is oxygen or sulfur; where X or Y or X and Y may be a carbonyl or carbinol group; wherein the nitrogen may be independently attached to the benzene rings in the 2-, 3-, or 4-positions; where isomerism is present when X or Y or X and Y are said carbinol groups; and wherein n is greater than 1 and equals the number of mers per molecule.
Claim 4
Dependent Claim 196 words
A polyamic resin, comprising a chain of recurring units of the formula characterized in that A' is and B is where R may be an aliphatic organic tetravalent radical containing at least two carbon atoms with no more than two carbonyl groups being attached to any one carbon atom of said tetravalent radical or where R may be a cycloaliphatic or aromatic tetravalent radical containing at least one ring with the four carbonyl groups being attached directly to separate carbon atoms in one or two rings of said radical and with each pair of carbonyl groups being attached to adjacent carbon atoms in said ring or rings of said radical; where R 1 and R 2 may be hydrogen or the same or different hydrocarbon monovalent radicals; where Z is oxygen or sulfur; where X or Y or X and Y may be a carbonyl or carbinol group; wherein the nitrogen may be independently attached to the benzene rings in the 2-, 3-, or 4-positions; where isomerism is present when X or Y or X and Y are said carbinol groups; and wherein n is greater than 1 and equals the number of mers per molecule.
Claim 5
Dependent Claim 144 words
The resin of Claim 1 or 2, characterized in that R is the tetravalent residue derived from a 3,3',4,4'-benzophenone tetracarboxylic acid compound, Z is oxygen or sulfur, X and Y are carbonyl groups, and both nitrogens are in the 3-position; or characterized in that R is the tetravalent residue derived from a 3,3',4,4'-benzophenone tetracarboxylic acid compound, Z is oxygen, X and Y are carbinol groups, and both nitrogens are in the 3-position; or characterized in that R is the tetravalent residue derived from a 3,3',4,4'-benzophenone tetracarboxylic acid compound, Z is oxygen, X and Y are carbonyl groups, carbinol groups, or mixtures of carbonyl and carbinol groups, and both nitrogens are in the 4-position; or characterized in that R is the tetravalent residue derived from a pyromellitic acid compound, Z is oxygen, X and Y are carbonyl groups, and both nitrogens are in the 3-position.
Claim 6
Dependent Claim 223 words
An end-capped polyimide resin, comprising a chain of recurring units having one or more of the formulas: or characterized in that A is and B is where R 3 is an inert or polymerizable monovalent organic radical derived from an aliphatic, cycloaliphatic, or aromatic primary monoamine; R 4 is an inert or polymerizable monovalent organic radical derived from an aliphatic, cycloaliphatic, or aromatic monoanhydride; where R may be an aliphatic organic tetravalent radical containing at least two carbon atoms with no more than two carbonyl groups being attached to any one carbon atom of said tetravalent radical or where R may be a cycloaliphatic or aromatic tetravalent radical containing at least one ring with the four carbonyl groups being attached directly to separate carbon atoms in one or two rings of said radical and with each pair of carbonyl groups being attached to adjacent carbon atoms in said ring or rings of said radical; where Z is oxygen or sulfur; wherein X or Y or X and Y may be a carbonyl or carbinol group; wherein the nitrogens may be independently attached to the benzene rings in the 2-, 3-, or 4-positions; where isomerism is present when X or Y or X and Y are said carbinol groups; and where m is one or greater and equals the number of mers per molecule.
Claim 7
Dependent Claim 223 words
An end-capped polyimide resin, comprising a chain of recurring units having one or more of the formulas: or characterized in that A is and B is where R 3 is an inert or polymerizable monovalent organic radical derived from an aliphatic, cycloaliphatic, or aromatic primary monoamine; R 4 is an inert or polymerizable monovalent organic radical derived from an aliphatic, cycloaliphatic, or aromatic monoanhydride; where R may be an aliphatic organic tetravalent radical containing at least two carbon atoms with no more than two carbonyl groups being attached to any one carbon atom of said tetravalent radical or where R may be a cycloaliphatic or aromatic tetravalent radical containing at least one ring with the four carbonyl groups being attached directly to separate carbon atoms in one or two rings of said radical and with each pair of carbonyl groups being attached to adjacent carbon atoms in said ring or rings of said radical; where Z is oxygen or sulfur; wherein X or Y or X and Y may be a carbonyl or carbinol group; wherein the nitrogens may be independently attached to the benzene rings in the 2-, 3-, or 4-positions; where isomerism is present when X or Y or X and Y are said carbinol groups; and where m is one or greater and equals the number of mers per molecule.
Claim 8
Dependent Claim 241 words
An end-capped polyamic resin, comprising a chain of recurring units having one or more of the following formulas: or characterized in that A' is and B is where R 3 is an inert or polymerizable monovalent organic radical derived from an aliphatic, cycloaliphatic, or aromatic primary monoamine; R 4 is an inert or polymerizable monovalent organic radical derived from an aliphatic, cycloaliphatic, or aromatic monoanhydride; where R may be an aliphatic organic tetravalent radical containing at least two carbon atoms with no more than two carbonyl groups being attached to any one carbon atom of said tetravalent radical or where R may be a cycloaliphatic or aromatic tetravalent radical containing at least one ring with the four carbonyl groups being attached directly to separate carbon atoms in one or two rings of said radical and with each pair of carbonyl groups being attached to adjacent carbon atoms in said ring or rings of said radical; where R 1 and R 2 may be hydrogen or the same or different hydrocarbon monovalent radicals; where Z is oxygen or sulfur; where X or Y or X and Y may be a carbonyl or carbinol group; wherein the nitrogens may be independently attached to the benzene rings in the 2-, 3-, or 4-positions; where isomerism is present when X or Y or X and Y are said carbinol groups; and where m is one or greater and equals the number of mers per molecule.
Claim 9
Dependent Claim 241 words
An end-capped polyamic resin, comprising a chain of recurring units having one or more of the following formulas: or characterized in that A' is and B is where R 3 is an inert or polymerizable monovalent organic radical derived from an aliphatic, cycloaliphatic, or aromatic primary monoamine; R 4 is an inert or polymerizable monovalent organic radical derived from an aliphatic, cycloaliphatic, or aromatic monoanhydride; where R may be an aliphatic organic tetravalent radical containing at least two carbon atoms with no more than two carbonyl groups being attached to any one carbon atom of said tetravalent radical or where R may be a cycloaliphatic or aromatic tetravalent radical containing at least one ring with the four carbonyl groups being attached directly to separate carbon atoms in one or two rings of said radical and with each pair of carbonyl groups being attached to adjacent carbon atoms in said ring or rings of said radical; where R 1 and R 2 may be hydrogen or the same or different hydrocarbon monovalent radicals; where Z is oxygen or sulfur; where X or Y or X and Y may be a carbonyl or carbinol group; wherein the nitrogens may be independently attached to the benzene rings in the 2-, 3-, or 4-positions; where isomerism is present when X or Y or X and Y are said carbinol groups; and where m is one or greater and equals the number of mers per molecule.
Claim 10
Dependent Claim 94 words
The resin of Claim 4 or 5, characterized in that R is the tetravalent residue dervied from a 3,3',4,4'-benzophenone tetracarboxylic acid compound, Z is oxygen, X and Y are carbonyl groups, both nitrogens are in the 3-position, and R 3 is a polymerizable monovalent organic radical derived from 3-aminophenyl acetylene; or characterized in that R is the tetravalent residue derived from a 3,3',4,4'-benzophenone tetracarboxylic acid compound, Z is oxygen, X and Y are carbonyl groups, both nitrogens are in the 3-position, and R 4 is a polymerizable monovalent organic radical derived from cis-endo-5-norbornene-2,3-dicarboxylic anhydride.
Claim 11
Dependent Claim 17 words
The resin characterized in that it results from the addition polymerization of the composition of Claim 6.

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