EP0223958A2
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EP
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Crosslinked copolyamideimides and method for their preparation
Assignee: General Electric Co
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Filing: 1986-09-23
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Granted: —
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Expires: 2006-09-23
Abstract
Abstract Carboxy-terminated prepolymers are prepared by the reaction of a diamine, preferably an aromatic diamine, or a mixture thereof with a triamine, with a carboxy anhydride such as trimellitic anhydride and a dianhydride such as bisphenol A dianhydride. The prepolymers, or functional derivatives thereof, are then reacted with a diisocyanate or diamine, or a mixture thereof with a triisocyanate or triamine, preferably an aromatic diisocyanate, to produce copolyamideimides. The products prepared using triamines or triisocyanates are crosslinked. Other products containing alkyl or alicyclic groups attached to aromatic radicals can be oxidatively crosslinked, e.g., by heating in air.
Inventors
- 👤 Donald Allen Bolon
- 👤 Thomas Bert Gorczyca
Bibliographic Details
Application Number
—
Jurisdiction
EP
Data Source
google_patents
Last Synchronized
2026-11-08 03:02
CPC Classifications
C; C08; C08G; C08G73/00; C08G73/06; C08G73/10; C08G73/1067; C08G73/1071; C08G18/00; C08G18/06; C08G18/28; C08G18/30; C08G18/38; C08G18/3819; C08G18/3821; C08G18/40; C08G18/64; C08G18/6415; C08G18/6438; C08G73/1003; C08G73/1007; C08G73/101; C08G73/1014; C08G73/1046; C08G73/105; C08G73/1057; C08G73/106; C08G73/14; H; H01; H01B; H01B3/00; H01B3/18; H01B3/30; H01B3/303; H01B3/306
Claims Analysis
Total Claims: 31
Claim 1
Independent Claim
152 words
A method for preparing a carboxy-terminated prepolymer which comprises reacting, under conditions whereby all water of reaction is removed: (A) at least one polyamine having the formula wherein R 1 is a divalent aromatic hydrocarbon radical containing about 6-20 carbon atoms or halogenated derivative thereof, alkylene or cycloalkylene radical containing about 2-20 carbon atoms, or bis-alkylenepoly(dialkylsiloxane) radical; with (E) at least one carboxy anhydride having the formula wherein R 2 is a trivalent aliphatic radical containing about 2-20 carbon atoms or aromatic radical containing about 6-20 carbon atoms, and (C) at least one dianhydride having the formula wherein R 3 is a tetravalent aliphatic radical containing about 2-20 carbon atoms or aromatic radical containing about 6-20 carbon atoms; the molar ratio of reagent C to reagent B being at least about 0.25:1 and the ratio of equivalents of reagent A to anhydride equivalents of reagents B and C combined being about 1:1.
Claim 2
Independent Claim
152 words
A method for preparing a carboxy-terminated prepolymer which comprises reacting, under conditions whereby all water of reaction is removed: (A) at least one polyamine having the formula wherein R 1 is a divalent aromatic hydrocarbon radical containing about 6-20 carbon atoms or halogenated derivative thereof, alkylene or cycloalkylene radical containing about 2-20 carbon atoms, or bis-alkylenepoly(dialkylsiloxane) radical; with (E) at least one carboxy anhydride having the formula wherein R 2 is a trivalent aliphatic radical containing about 2-20 carbon atoms or aromatic radical containing about 6-20 carbon atoms, and (C) at least one dianhydride having the formula wherein R 3 is a tetravalent aliphatic radical containing about 2-20 carbon atoms or aromatic radical containing about 6-20 carbon atoms; the molar ratio of reagent C to reagent B being at least about 0.25:1 and the ratio of equivalents of reagent A to anhydride equivalents of reagents B and C combined being about 1:1.
Claim 3
Dependent Claim
89 words
A method according to claim 1 wherein reagent A is at least one diamine; R 2 is an aromatic hydrocarbon radical; R 3 has formula XI, wherein R 7 is oxygen, sulfur, -S0 2 -, lower alkylene or -O-R 8 -O-, and R 8 is a divalent radical derived from benzene or a substituted benzene, biphenyl or a substituted biphenyl, or a diphenylalkane which optionally contains substituents on one or both aromatic radicals; and wherein the reaction mixture also contains a catalytic amount of at least one tertiary amine.
Claim 4
Dependent Claim
33 words
A method according to claim 2 wherein reagent B is trimellitic anhydride, reagent C is bisphenol A dianhydride, and the molar ratio of reagent C to reagent B is at least about 0.1:1.
Claim 5
Dependent Claim
14 words
A method according to claim 3 wherein R 1 is an aromatic hydrocarbon radical.
Claim 6
Dependent Claim
14 words
A method according to claim 4 wherein reagent A is m-phenylenediamine, m-toluenediamine or 4,4'-diaminodiphenylmethane.
Claim 7
Dependent Claim
10 words
A carboxy-terminated prepolymer prepared by the method of claim 1.
Claim 8
Dependent Claim
10 words
A carboxy-terminated prepolymer prepared by the method of claim 5.
Claim 9
Dependent Claim
86 words
A carboxy-terminated prepolymer having the formula wherein R 1 is a divalent aromatic hydrocarbon radical containing about 6-20 carbon atoms or halogenated derivative thereof, alkylene or cycloalkylene radical containing about 2-20 carbon atoms, or bis-alkylenepoly(dialkylsiloxane) radical; R 2 is a trivalent aliphatic radical containing about 2-20 carbon atoms or aromatic radical containing about 6-20 carbon atoms; R 3 is a tetravalent aliphatic radical containing about 2-20 carbon atoms or aromatic radical containing about 6-20 carbon atoms; and the average value of n is at least 0.5.
Claim 10
Dependent Claim
86 words
A carboxy-terminated prepolymer having the formula wherein R 1 is a divalent aromatic hydrocarbon radical containing about 6-20 carbon atoms or halogenated derivative thereof, alkylene or cycloalkylene radical containing about 2-20 carbon atoms, or bis-alkylenepoly(dialkylsiloxane) radical; R 2 is a trivalent aliphatic radical containing about 2-20 carbon atoms or aromatic radical containing about 6-20 carbon atoms; R 3 is a tetravalent aliphatic radical containing about 2-20 carbon atoms or aromatic radical containing about 6-20 carbon atoms; and the average value of n is at least 0.5.
Claim 11
Dependent Claim
67 words
A prepolymer according to claim 8 wherein R 2 is an aromatic hydrocarbon radical and R 3 has the formula wherein R 7 is oxygen, sulfur, -S0 2 -, lower alkylene or -O-R 8 -O- and R 8 is a divalent radical derived from benzene or a substituted benzene, biphenyl or a substituted biphenyl, or a diphenylalkane which optionally contains substituents on one or both aromatic radicals.
Claim 12
Dependent Claim
27 words
A prepolymer according to claim 9 wherein R 2 has the formula R 3 has the formula and the average value of n is at least 1.
Claim 13
Dependent Claim
14 words
A prepolymer according to claim 10 wherein R 1 is an aromatic hydrocarbon radical.
Claim 14
Dependent Claim
14 words
A prepolymer according to claim 11 wherein R 1 has one of the formulas
Claim 15
Dependent Claim
102 words
A method for preparing a copolyamideimide which comprises reacting, at a temperature within the range of about 150-225°C, (D) a prepolymer according to claim 1, or a functional derivative thereof, with (E) at least one compound selected from the group consisting of polyisocyanates having the formula polyamines having the formula and functional derivatives thereof, wherein: R 4 is a divalent polymeric radical, aromatic hydrocarbon radical containing about 6-20 carbon atoms or halogenated derivative thereof, alkylene or cycloalkylene radical containing about 2-20 carbon atoms, or bis-alky- lenepoly(dialkylsiloxane) radical; and each of R and R 6 is independently hydrogen or a lower hydrocarbon radical.
Claim 16
Dependent Claim
26 words
A method according to claim 13 wherein reagent E is a mixture of at least one diisocyanate with at least one triisocyanate or functional derivative thereof.
Claim 17
Dependent Claim
59 words
A method according to claim 13 wherein each of R 1 and R 4 is an aromatic hydrocarbon radical, reagent D is said prepolymer, reagent E is at least one diisocyanate, R 2 has the formula R 3 has the formula and the ratio of equivalents of reagent D to reagent E is from about 0.67:1 to about 1.5:1.
Claim 18
Dependent Claim
22 words
A method according to claim 15 wherein reagent E is at least one of 2,4-toluene diisocyanate, 2,6-toluene diisocyanate and 4,4'-methylene bis(phenyl isocyanate).
Claim 19
Dependent Claim
9 words
A copolyamideimide prepared by the method of claim 13.
Claim 20
Dependent Claim
108 words
A copolyamideimide consisting essentially of units having the formula wherein: each of R and R 4 is independently a divalent aromatic hydrocarbon radical containing about 6-20 carbon atoms or halogenated derivative thereof, alkylene or cycloalkylene radical containing about 2-20 carbon atoms, or bis-alkylenepoly(dialkylsiloxane) radical; R 2 is a trivalent aliphatic radical containing about 2-20 carbon atoms or aromatic radical containing about 6-20 carbon atoms; R 3 is a tetravalent aliphatic radical containing about 2-20 carbon atoms or aromatic radical containing about 6-20 carbon atoms; each of R 5 and R 6 is independently hydrogen or a hydrocarbon radical; and the average value of n is at least 0.5.
Claim 21
Dependent Claim
108 words
A copolyamideimide consisting essentially of units having the formula wherein: each of R and R 4 is independently a divalent aromatic hydrocarbon radical containing about 6-20 carbon atoms or halogenated derivative thereof, alkylene or cycloalkylene radical containing about 2-20 carbon atoms, or bis-alkylenepoly(dialkylsiloxane) radical; R 2 is a trivalent aliphatic radical containing about 2-20 carbon atoms or aromatic radical containing about 6-20 carbon atoms; R 3 is a tetravalent aliphatic radical containing about 2-20 carbon atoms or aromatic radical containing about 6-20 carbon atoms; each of R 5 and R 6 is independently hydrogen or a hydrocarbon radical; and the average value of n is at least 0.5.
Claim 22
Dependent Claim
48 words
A copolyamideimide according to claim 18 wherein each of R 1 and R 4 is an aromatic hydrocarbon radical, R 2 has formula X, R 3 has the formula each of R 5 and R 6 is hydrogen and the average value of n is at least 1.
Claim 23
Dependent Claim
20 words
A copolyamideimide according to claim 19 wherein R 4 is at least one of the 2,4-tolylene, 2,6-tolylene and 4,4'-methylenebis-phenyl radicals.
Claim 24
Independent Claim
157 words
A method for preparing a crosslinked polymer from a copolyamideimide comprising structural units having the formulas wherein: each of R 1 and R 4 is independently a divalent aromatic hydrocarbon radical containing about 6-20 carbon atoms or halogenated derivative thereof, alkylene or cycloalkylene radical containing about 2-20 carbon atoms, or bis-alkylenepoly(dialkylsiloxane) radical; R 2 is a trivalent aliphatic radical containing about 2-20 carbon atoms or aromatic radical containing about 6-20 carbon atoms; R 3 is a tetravalent aliphatic radical containing about 2-20 carbon atoms or aromatic radical containing about 6-20 carbon atoms; and each of R 5 and R 6 is independently hydrogen or a hydrocarbon radical; said structural units of formula XVII containing at least one aromatic radical having at least one alkyl or alicyclic substituent; which comprises contacting said copolyamideimide with an oxidizing agent and heating said copolyamideimide at a temperature within the range from its glass transition temperature to just below its degradation temperature.
Claim 25
Independent Claim
157 words
A method for preparing a crosslinked polymer from a copolyamideimide comprising structural units having the formulas wherein: each of R 1 and R 4 is independently a divalent aromatic hydrocarbon radical containing about 6-20 carbon atoms or halogenated derivative thereof, alkylene or cycloalkylene radical containing about 2-20 carbon atoms, or bis-alkylenepoly(dialkylsiloxane) radical; R 2 is a trivalent aliphatic radical containing about 2-20 carbon atoms or aromatic radical containing about 6-20 carbon atoms; R 3 is a tetravalent aliphatic radical containing about 2-20 carbon atoms or aromatic radical containing about 6-20 carbon atoms; and each of R 5 and R 6 is independently hydrogen or a hydrocarbon radical; said structural units of formula XVII containing at least one aromatic radical having at least one alkyl or alicyclic substituent; which comprises contacting said copolyamideimide with an oxidizing agent and heating said copolyamideimide at a temperature within the range from its glass transition temperature to just below its degradation temperature.
Claim 26
Dependent Claim
25 words
. A method according to claim 21 wherein the copolyamideimide is heated with oxygen or air at a temperature within the range of about 225-325°C.
Claim 27
Dependent Claim
46 words
A method according to claim 22 wherein R 1 is an aromatic hydrocarbon radical, R 2 has the formula R 3 has the formula R 4 is at least one of the 2,4-tolylene and 2,6-tolylene radicals, and each of R 5 and R 6 is hydrogen.
Claim 28
Dependent Claim
10 words
A crosslinked polymer prepared by the method of claim 22.
Claim 29
Dependent Claim
10 words
A crosslinked polymer prepared by the method of claim 23.
Claim 30
Dependent Claim
24 words
An article comprising a metallic electrical conductor having on at least a portion thereof an insulating coating comprising a polymer according to claim 17.
Claim 31
Dependent Claim
24 words
An article comprising a metallic electrical conductor having on at least a portion thereof an insulating coating comprising a polymer according to claim 24.
References Cited (Backward Citations)
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