US3972960A
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Heat-stable polyimide resin modified by unsaturated polyester
Assignee: Rhone Poulenc SA
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Filing: 1974-03-05
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Granted: 1976-08-03
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Expires: 1994-03-05
Abstract
Abstract New heat-stable resins are provided having good mechanical and electrical properties combined with chemical inertness at temperatures of 200° to 300°C, which resins comprise three-dimensional recurring units of the general formula: ##EQU1## in which, in any particular recurring unit: A IS ZERO OR AN INTEGER FROM 1 TO 5; ##EQU2## denotes a radical of the general formula ##EQU3## in which Y represents H, CH 3 or Cl; G denotes a monovalent aromatic radical; and A denotes a divalent organic radical possessing at least two carbon atoms, Such that there are on average, at least 4.4 and at most about 20>D 1 < radicals per ##EQU4## radical, and optionally, units and/or molecules of the general formula ##EQU5## IN WHICH: T denotes a monovalent organic radical; T 1 denotes a radical of the general formula: ##EQU6## or a radical of the general formula: ##EQU7## b is zero or an integer from 1 to 4; and A, D 1 and G are as defined in claim 1; such that there are at most about 30 ##EQU8## radicals per 100 ##EQU9## radicals, and which is modified by the addition, before curing, of an unsaturated polyester and/or polymerizable monomer other than an imide, containing at least one vinyl, maleic, allyl or acrylic --CH=C< group.
Inventors
- 👤 Michel Bargain
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-24 19:30
CPC Classifications
C; C08; C08G; C08G73/00; C08G73/06; C08G73/10; C08G73/12; C08L; C08L79/00; C08L79/04; C08L79/08; C08L79/085; Y; Y10; Y10S; Y10S525/00; Y10S525/929
Claims Analysis
Total Claims: 20
Claim 1
Independent Claim
249 words
A heat-stable cured resin which consists essentially of three-dimensional recurring units of the general formula: ##EQU10##in which, in any particular recurring unit a is zero or an integer from 1 to 5; ##EQU11## denotes a radical of the general formula: ##EQU12##in which Y represents H, CH 3 or Cl; G denotes a monovalent carbocyclic aromatic radical; and A denotes an alkylene radical having less than 13 carbon atoms, a phenylene or cyclohexylene radical or one of the radicals of the formulae: ##SPC4## wherein n represents an integer from 1 to 3, or a divalent radical having 12 to 30 carbon atoms consisting of phenylene or cyclohexylene radicals linked to one another by a simple valency bond or by --O-- or --S--, an alkylene group with 1 to 3 carbon atoms, --CO--, --SO 2 --, --NR 1 --, --N=N--, --CONH--, --COO--, --P(O)R 1 --, --CONH--X--NHCO--, ##SPC5## wherein R 1 represents a hydrogen atom, an alkyl radical with 1 to 4 carbon atoms, a phenyl radical or a cyclohexyl radical and X represents an alkylene radical with less than 13 carbon atoms, such that there are, on average, at least 4.4 and at most about 20 >D 1 < radicals per ##EQU13##radical and which is modified by the addition, before curing of the resin, of an unsaturated polyester of at least one polycarboxylic acid and at least one polyol, at least one containing olefinic unsaturation, in an amount from 5 to 50% by weight based on the weight of the reactants.
Claim 2
Dependent Claim
249 words
A heat-stable cured resin which consists essentially of three-dimensional recurring units of the general formula: ##EQU10##in which, in any particular recurring unit a is zero or an integer from 1 to 5; ##EQU11## denotes a radical of the general formula: ##EQU12##in which Y represents H, CH 3 or Cl; G denotes a monovalent carbocyclic aromatic radical; and A denotes an alkylene radical having less than 13 carbon atoms, a phenylene or cyclohexylene radical or one of the radicals of the formulae: ##SPC4## wherein n represents an integer from 1 to 3, or a divalent radical having 12 to 30 carbon atoms consisting of phenylene or cyclohexylene radicals linked to one another by a simple valency bond or by --O-- or --S--, an alkylene group with 1 to 3 carbon atoms, --CO--, --SO 2 --, --NR 1 --, --N=N--, --CONH--, --COO--, --P(O)R 1 --, --CONH--X--NHCO--, ##SPC5## wherein R 1 represents a hydrogen atom, an alkyl radical with 1 to 4 carbon atoms, a phenyl radical or a cyclohexyl radical and X represents an alkylene radical with less than 13 carbon atoms, such that there are, on average, at least 4.4 and at most about 20 >D 1 < radicals per ##EQU13##radical and which is modified by the addition, before curing of the resin, of an unsaturated polyester of at least one polycarboxylic acid and at least one polyol, at least one containing olefinic unsaturation, in an amount from 5 to 50% by weight based on the weight of the reactants.
Claim 3
Dependent Claim
74 words
The resin according to claim 1 which also contains units and/or molecules of the general formula: ##STR18##in which: T denotes a monovalent organic radical; T 1 denotes a radical of the general formula: ##STR19##or a radical of the general formula: ##STR20##b is zero or a integer from 1 to 4; and A, D 1 and G are as defined in claim 1; such that there are at most about 30 ##STR21##radicals per 100 ##STR22##radicals.
Claim 4
Dependent Claim
135 words
The resin according to claim 1 in which A denotes an alkylene radical having less than 13 carbon atoms, a phenylene or cyclohexylene radical or one of the radicals of the formulae: ##SPC6## wherein n represents an integer from 1 to 3, a divalent radical having 12 to 30 carbon atoms consisting of phenylene or cyclohexylene radicals linked to one another by a simple valency bond or by an inert atom or group --O-- or --S--, an alkylene group with 1 to 3 carbon atoms, --CO--, --SO 2 --, NR 1 --, --N=N--, --CONH--, --COO--, --P(O)R 1 --, --CONH--X--NHCO--, ##SPC7## wherein R 1 represents a hydrogen atom, an alkyl radical with 1 to 4 carbon atoms, a phenyl radical or a cyclohexyl radical and X represents an alkylene radical with less than 13 carbon atoms.
Claim 5
Dependent Claim
11 words
The resin according to claim 3 in which A denotes: ##SPC8##
Claim 6
Dependent Claim
24 words
The resin according to claim 1 in which G denotes a phenyl radical optionally substituted by a chlorine, fluorine, methyl, methoxy or nitro group.
Claim 7
Dependent Claim
13 words
The resin according to claim 5 in which G denotes a phenyl radical.
Claim 8
Dependent Claim
81 words
The resin according to claim 2 in which T denotes an alkyl radical of 1 to 18 carbon atoms, a phenyl or cyclohexyl radical or a ##SPC9## wherein n represents an integer from 1 to 3, or a phenyl and a phenylene radical connected by a single bond or by --O--, --S--, an alkylene radical of 1 to 3 carbon atoms, --CO--, --SO 2 --, --NR 1 --, --N=N--, --CONH-- or --COO-- wherein R 1 is as defined in claim 3.
Claim 9
Dependent Claim
13 words
The resin according to claim 7 in which T denotes a phenyl radical.
Claim 10
Dependent Claim
38 words
The resin according to claim 1 which also comprises an aromatic compound containing 2 to 4 benzene rings which is not sublimable at atmospheric pressure up to 250° C. and which has a boiling point above 250° C.
Claim 11
Dependent Claim
11 words
The resin according to claim 9 which also comprises a terphenyl.
Claim 12
Dependent Claim
21 words
The resin according to claim 1 in which the polyester is one derived from chlorendic acid, maleic acid and ethylene glycol.
Claim 13
Dependent Claim
102 words
Process for the preparation of a resin as claimed in claim 1 which comprises heating at between 50° and 350° C., at least one alazine of the general formula: G -- CH = N -- N = CH -- G in which the symbol G is as defined in claim 1 with at least one bis-imide of the general formula: ##STR23##in which A and Y are as defined in claim 1, in such amounts that on average at least 2.2 and at most 10 mols of bis-imide are present per mol of alazine, and an unsaturated polyester as defined in claim 1.
Claim 14
Dependent Claim
57 words
Process according to claim 12 in which a mono-imide of the general formula: ##STR24##in which G, A, Y are as defined in claim 12 and T is as defined in claim 2 is heated with the alazine and bis-imide in an amount such that at most 30 mols of mono-imide are present per 100 mols of bis-imide.
Claim 15
Dependent Claim
48 words
Process according to claim 12 in which a prepolymer is first prepared by heating the mixture in bulk at a temperature of between 80° and 180° C. until a homogeneous liquid is obtained and the prepolymer is then cured by subsequent heating at between 150° and 350° C.
Claim 16
Dependent Claim
45 words
Process according to claim 12 in which a prepolymer is prepared by heating the reactants in solution in a polar solvent at a temperature of between 50° and 180° C. and the prepolymer is then cured by subsequent heating at between 150° and 300° C.
Claim 17
Dependent Claim
19 words
Process according to claim 12 in which the polyester is one from chlorendic acid, maleic acid and ethylene glycol.
Claim 18
Dependent Claim
16 words
Process according to claim 12 which comprises heating the alazine and bis-imide with an unsaturated polyester.
Claim 19
Dependent Claim
19 words
A shapable heat curable prepolymer obtained by carrying out the first step in the process claimed in claim 14.
Claim 20
Dependent Claim
20 words
A shapable heat curable prepolymer solution obtained by carrying out the first step in the process claimed in claim 15.
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) | 1979-08-03 | 1980-02-02 | 1980-08-03 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1983-08-03 | 1984-02-02 | 1984-08-03 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1987-08-03 | 1988-02-02 | 1988-08-03 | $7700.00 | Window Closed / Lapsed |