US3998787A
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Heat-stable polyimide resins from bis-imide and aldehyde-azine
Assignee: Individual
•
Filing: 1972-02-22
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Granted: 1976-12-21
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Expires: 1992-02-22
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: ##STR1## in which, in any particular recurring unit: A IS ZERO OR AN INTEGER FROM 1 TO 5; ##STR2## denotes a radical of the general formula ##STR3## 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 ##STR4## radical, and optionally, units and/or molecules of the general formula ##STR5## in which: T denotes a monovalent organic radical; T 1 denotes a radical of the general formula: ##STR6## or a radical of the general formula: ##STR7## 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 ##STR8## radicals per 100 ##STR9## radicals.
Inventors
- 👤 Michel Bargain
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-23 09:37
CPC Classifications
C; C08; C08G; C08G73/00; C08G73/06; C08G73/10; C08G73/12; Y; Y10; Y10T; Y10T428/00; Y10T428/31504; Y10T428/31551; Y10T428/31623
Claims Analysis
Total Claims: 18
Claim 1
Independent Claim
216 words
A shapable heat-curable thermosetting prepolymer obtained by heating at least one alazine of the general formula: G -- CH = N -- N = CH -- G in which the symbol G denotes a monovalent carbocyclic aromatic radical with at least one bis-imide of the general formula: ##STR30## in which Y represents H, CH 3 or Cl 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: ##STR31## wherein n represents an integer for 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--, ##STR32## 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. in such amounts that on average at least 2.2 and at most 10 mols of bis-imide are present per mole of alazine, in a polar solvent at a temperature of between 50° and 180° C.
Claim 2
Dependent Claim
216 words
A shapable heat-curable thermosetting prepolymer obtained by heating at least one alazine of the general formula: G -- CH = N -- N = CH -- G in which the symbol G denotes a monovalent carbocyclic aromatic radical with at least one bis-imide of the general formula: ##STR30## in which Y represents H, CH 3 or Cl 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: ##STR31## wherein n represents an integer for 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--, ##STR32## 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. in such amounts that on average at least 2.2 and at most 10 mols of bis-imide are present per mole of alazine, in a polar solvent at a temperature of between 50° and 180° C.
Claim 3
Dependent Claim
214 words
A shapable, heat-curable thermosetting prepolymer obtained by heating at least one alazine of the general formula: G -- CH = N -- N = CH -- G in which the symbol G denotes a monovalent carbocyclic aromatic radical with at least one bis-imide of the general formula: ##STR33## in which Y represents H, CH 3 or Cl 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: ##STR34## 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--, ##STR35## 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, in such amounts that on average at least 2.2 and at most 10 mols of bis-imide are present per mol of alazine, in bulk at a temperature of between 80° and 180° C.
Claim 4
Dependent Claim
214 words
A shapable, heat-curable thermosetting prepolymer obtained by heating at least one alazine of the general formula: G -- CH = N -- N = CH -- G in which the symbol G denotes a monovalent carbocyclic aromatic radical with at least one bis-imide of the general formula: ##STR33## in which Y represents H, CH 3 or Cl 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: ##STR34## 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--, ##STR35## 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, in such amounts that on average at least 2.2 and at most 10 mols of bis-imide are present per mol of alazine, in bulk at a temperature of between 80° and 180° C.
Claim 5
Dependent Claim
100 words
A shapable heat-curable thermosetting prepolymer obtained by heating at least one alazine of the general formula: G -- CH = N -- N = CH -- G in which the symbol G denotes a monovalent carbocyclic aromatic radical with at least one bis-imide of the general formula: ##STR36## in which Y represents H, CH 3 or Cl and A denotes a divalent carbocyclic aromatic radical in such amounts that on average at least 2.2 and at most 10 mols of bis-imide are present per mole of alazine, in a polar solvent at a temperature of between 50° and 180° C.
Claim 6
Dependent Claim
100 words
A shapable heat-curable thermosetting prepolymer obtained by heating at least one alazine of the general formula: G -- CH = N -- N = CH -- G in which the symbol G denotes a monovalent carbocyclic aromatic radical with at least one bis-imide of the general formula: ##STR36## in which Y represents H, CH 3 or Cl and A denotes a divalent carbocyclic aromatic radical in such amounts that on average at least 2.2 and at most 10 mols of bis-imide are present per mole of alazine, in a polar solvent at a temperature of between 50° and 180° C.
Claim 7
Dependent Claim
98 words
A shapable heat-curable thermosetting prepolymer obtained by heating at least one alazine of the general formula: G -- CH = N -- N = CH -- G in which the symbol G denotes a monovalent carbocyclic aromatic radical with at least one bis-imide of the general formula: ##STR37## in which Y represents H, CH 3 or Cl and A denotes a divalent carbocyclic aromatic radical in such amounts that on average at least 2.2 and at most 10 mols of bis-imide are present per mol of alazine, in bulk, at a temperature of between 80° and 180° C.
Claim 8
Dependent Claim
98 words
A shapable heat-curable thermosetting prepolymer obtained by heating at least one alazine of the general formula: G -- CH = N -- N = CH -- G in which the symbol G denotes a monovalent carbocyclic aromatic radical with at least one bis-imide of the general formula: ##STR37## in which Y represents H, CH 3 or Cl and A denotes a divalent carbocyclic aromatic radical in such amounts that on average at least 2.2 and at most 10 mols of bis-imide are present per mol of alazine, in bulk, at a temperature of between 80° and 180° C.
Claim 9
Dependent Claim
203 words
A heat-stable cured thermoset resin which consists essentially of three-dimensional recurring units of the general formula: ##STR38## in which, in any particular recurring unit a is zero or an interger from 1 to 5; ##STR39## denotes a radical of the general formula: ##STR40## 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: ##STR41## 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 --0--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--, ##STR42## 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 ##STR43## radical.
Claim 10
Dependent Claim
203 words
A heat-stable cured thermoset resin which consists essentially of three-dimensional recurring units of the general formula: ##STR38## in which, in any particular recurring unit a is zero or an interger from 1 to 5; ##STR39## denotes a radical of the general formula: ##STR40## 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: ##STR41## 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 --0--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--, ##STR42## 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 ##STR43## radical.
Claim 11
Dependent Claim
13 words
The resin according to claim 5, in which G denotes a phenyl radical.
Claim 12
Dependent Claim
41 words
The resin according to claim 5, which also consists essentially of an aromatic compound containing 2 to 4 benzene rings which is not sublimable at atmospheric pressure up to 250° C and which was has a boiling point above 250° C.
Claim 13
Dependent Claim
13 words
The resin according to claim 7 wherein the aromatic compound is a terphenyl.
Claim 14
Dependent Claim
23 words
The resin according to claim 5 in which G denotes a phenyl radical substituted by a chlorine, fluorine, methyl, methoxy or nitro group.
Claim 15
Dependent Claim
81 words
A heat-stable cured thermoset resin which consists essentially of three-dimensional recurring units of the general formula: ##STR44## in which, in any particular recurring unit a is zero or an integer from 1 to 5; ##STR45## denotes a radical of the general formula: ##STR46## in which Y represents H, CH 3 or Cl; G denotes a monovalent carbocyclic aromatic radical; and ##STR47## such that there are on average at least 4.4 and at most about 20>D 1 < radical per ##STR48## radical.
Claim 16
Dependent Claim
81 words
A heat-stable cured thermoset resin which consists essentially of three-dimensional recurring units of the general formula: ##STR44## in which, in any particular recurring unit a is zero or an integer from 1 to 5; ##STR45## denotes a radical of the general formula: ##STR46## in which Y represents H, CH 3 or Cl; G denotes a monovalent carbocyclic aromatic radical; and ##STR47## such that there are on average at least 4.4 and at most about 20>D 1 < radical per ##STR48## radical.
Claim 17
Dependent Claim
88 words
A heat stable cured thermoset resin which consists essentially of three-dimensional recurring units of the general formula: ##STR49## in which, in any particular recurring unit a is zero or an integer from 1 to 5; ##STR50## denotes a radical of the general formula: ##STR51## in which Y represents H, CH 3 or Cl; G denotes a monovalent carbocyclic aromatic radical; and A denotes a divalent carbocyclic aromatic radical such that there are on average at least 4.4 and at most about 20>D 1 < radicals per ##STR52## radical.
Claim 18
Dependent Claim
88 words
A heat stable cured thermoset resin which consists essentially of three-dimensional recurring units of the general formula: ##STR49## in which, in any particular recurring unit a is zero or an integer from 1 to 5; ##STR50## denotes a radical of the general formula: ##STR51## in which Y represents H, CH 3 or Cl; G denotes a monovalent carbocyclic aromatic radical; and A denotes a divalent carbocyclic aromatic radical such that there are on average at least 4.4 and at most about 20>D 1 < radicals per ##STR52## radical.
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) | 1979-12-21 | 1980-06-21 | 1980-12-21 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1983-12-21 | 1984-06-21 | 1984-12-21 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1987-12-21 | 1988-06-21 | 1988-12-21 | $7700.00 | Window Closed / Lapsed |