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US3944525A Expired / Lapsed US ⏱️ 0.0 years remaining

Crosslinked resins prepared from an N,N'-bis-imide and a schiff base

Assignee: Novartis Corp
•
Filing: 1973-10-03
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Granted: 1976-03-16
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Expires: 1993-10-03
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Abstract

Abstract Crosslinked resins are prepared by reacting an N,N'-bis-imide and a Schiff base at a temperature of from 100°C to 280°C. The crosslinked resins have good thermal stability and are useful for making adhesives, coatings, laminates and molded articles.

Inventors

  • 👤 Franklin P. Darmory
  • 👤 Marianne DiBenedetto

Bibliographic Details

Application Number —
Jurisdiction US
Data Source google_patents
Last Synchronized 2026-10-28 17:17
CPC Classifications
C; C08; C08G; C08G73/00; C08G73/06; C08G73/10; C08G73/12; C08G73/121; C08G73/122; C08G73/125; C08G73/126; C08G73/127; C08G73/128

Claims Analysis

Total Claims: 13
Claim 1
Independent Claim 377 words
A stable heat curable composition consisting essentially of (a) an unsaturated N,N'-bis-imide having the formula ##EQU9## wherein A is an alkylene group containing from 2 to 12 carbon atoms; cycloalkylene group containing from 4 to 6 carbon atoms, a xylylene group, an arylene group selected from phenylene, tolylene, biphenylene, naphthylene; a substituted arylene group of the formula ##SPC6## wherein Z is sulfur, carbonyl, --NH, N--(lower)alkyl, --O--, N-phenyl, sulfonyl, an alkylene group of from 1 to 3 carbon atoms, R 6 and R 7 are independent and each is hydrogen, chloro, or bromo, (lower)alkyl of from 1 to 5 carbon atoms, or (lower)alkoxy containing from 1 to 5 carbon atoms; Q is a divalent radical containing olefinic unsaturation having the formula ##EQU10## wherein R 3 is hydrogen, methyl, bromo or chloro; R 4 is hydrogen, methyl, bromo or chloro; From about 0.5 to 0.166 mole equivalents per mole equivalent of (a) of a Schiff base having the formula ##EQU11## wherein R 1 and R 2 independently is hydrogen, an alkyl group containing from 1 to 12 carbon atoms, an aryl group containing from 6 to 12 carbon atoms, an alkaryl group containing from 7 to 15 carbon atoms, an aralkyl group containing from 7 to 15 carbon atoms, chlorophenyl, alkoxyphenyl, said alkoxy containing from 1 to 5 carbon atoms, or together with the carbon to which they are attached form a monocyclic ring containing 5 to 6 carbon atoms, with the proviso that only one of R 1 or R 2 may be hydrogen at the same time; and A is an alkylene group containing from 2 to 12 carbon atoms; cycloalkylene group containing from 4 to 6 carbon atoms, a xylylene group, an arylene group selected from phenylene, tolylene, biphenylene, naphthylene, a substituted arylene group of the formula ##SPC7## wherein Z is sulfur, carbonyl, --NH, --N(lower)alkyl, --O--, --N-- phenyl, sulfonyl, an alkylene group of from 1 to 3 carbon atoms, R 6 and R 7 are independent and each is hydrogen, chloro, or bromo, (lower)alkyl of from 1 to 5 carbon atoms, (lower) alkoxy containing from 1 to 5 carbon atoms, or a group having the formula ##SPC8## wherein Y is a covalent bond or --NH, and R 8 is phenyl piperidino, hydrogen, diphenylamino or di(lower)alkyl amino.
Claim 2
Dependent Claim 377 words
A stable heat curable composition consisting essentially of (a) an unsaturated N,N'-bis-imide having the formula ##EQU9## wherein A is an alkylene group containing from 2 to 12 carbon atoms; cycloalkylene group containing from 4 to 6 carbon atoms, a xylylene group, an arylene group selected from phenylene, tolylene, biphenylene, naphthylene; a substituted arylene group of the formula ##SPC6## wherein Z is sulfur, carbonyl, --NH, N--(lower)alkyl, --O--, N-phenyl, sulfonyl, an alkylene group of from 1 to 3 carbon atoms, R 6 and R 7 are independent and each is hydrogen, chloro, or bromo, (lower)alkyl of from 1 to 5 carbon atoms, or (lower)alkoxy containing from 1 to 5 carbon atoms; Q is a divalent radical containing olefinic unsaturation having the formula ##EQU10## wherein R 3 is hydrogen, methyl, bromo or chloro; R 4 is hydrogen, methyl, bromo or chloro; From about 0.5 to 0.166 mole equivalents per mole equivalent of (a) of a Schiff base having the formula ##EQU11## wherein R 1 and R 2 independently is hydrogen, an alkyl group containing from 1 to 12 carbon atoms, an aryl group containing from 6 to 12 carbon atoms, an alkaryl group containing from 7 to 15 carbon atoms, an aralkyl group containing from 7 to 15 carbon atoms, chlorophenyl, alkoxyphenyl, said alkoxy containing from 1 to 5 carbon atoms, or together with the carbon to which they are attached form a monocyclic ring containing 5 to 6 carbon atoms, with the proviso that only one of R 1 or R 2 may be hydrogen at the same time; and A is an alkylene group containing from 2 to 12 carbon atoms; cycloalkylene group containing from 4 to 6 carbon atoms, a xylylene group, an arylene group selected from phenylene, tolylene, biphenylene, naphthylene, a substituted arylene group of the formula ##SPC7## wherein Z is sulfur, carbonyl, --NH, --N(lower)alkyl, --O--, --N-- phenyl, sulfonyl, an alkylene group of from 1 to 3 carbon atoms, R 6 and R 7 are independent and each is hydrogen, chloro, or bromo, (lower)alkyl of from 1 to 5 carbon atoms, (lower) alkoxy containing from 1 to 5 carbon atoms, or a group having the formula ##SPC8## wherein Y is a covalent bond or --NH, and R 8 is phenyl piperidino, hydrogen, diphenylamino or di(lower)alkyl amino.
Claim 3
Dependent Claim 13 words
A composition according to claim 1 which further contains a peroxide curing catalyst.
Claim 4
Dependent Claim 254 words
A composition according to claim 1 wherein a. is an unsaturated N,N'-bis-imide having the formula ##EQU12## wherein A is m or p-phenylene, biphenylene or alkylene group containing from 2 to 12 carbon atoms or a group having the formula ##SPC9## wherein X is --O--, sulfonyl, or alkylene group containing from 1 to 3 carbon atoms; and Q is a divalent radical containing olefinic unsaturation have the formula ##EQU13## wherein R 3 is hydrogen or methyl; b. is a Schiff base having the formula ##EQU14## wherein R 1 and R 2 independently is hydrogen, an alkyl group containing from 1 to 12 carbon atoms, phenyl group, tolyl, chlorophenyl, or alkoxyphenyl, said alkoxy containing from 1 to 5 carbon atoms, with the proviso that only one of R 1 and R 2 may be hydrogen at the same time; A is an alkylene group containing from 2 to 12 carbon atoms; cycloalkylene group containing from 4 to 6 carbon atoms, a xylylene group, an arylene group selected from phenylene, tolylene, biphenylene, naphthylene, a substituted arylene group of the formula ##SPC10## wherein Z is sulfur, carbonyl, --NH, N--(lower)alkyl, --O--, --N-phenyl, sulfonyl, an alkylene group of from 1 to 3 carbon atoms, R 6 and R 7 are independent and each is hydrogen, chloro, or bromo, (lower)alkyl of from 1 to 5 carbon atoms, (lower)alkoxy containing from 1 to 5 carbon atoms, or a group having the formula ##SPC11## where Y is a covalent bond or --NH, and R 8 is phenyl, piperidino, hydrogen, diphenylamino or di(lower)alkyl amino.
Claim 5
Dependent Claim 19 words
A composition according to claim 1 wherein the unsaturated N,N'-bis-imide is maleic N,N'-diphenylmethane-bis-imide, and the Schiff Base is 4,4'-methylenebis[N-(α-methylbenzylidene)aniline].
Claim 6
Dependent Claim 19 words
A composition according to claim 1 wherein the unsaturated N,N'-bis-imide is maleic N,N'-diphenylmethane-bis-imide and the Schiff Base is N,N'-dibenzylidene-metaphenylenediamine.
Claim 7
Dependent Claim 19 words
A composition according to claim 1 wherein the unsaturated N,N'-bis-imide is maleic N,N'-diphenylmethane-bis-imide and the Schiff Base is 4,4'-methylenebis(N-benzylideneaniline).
Claim 8
Dependent Claim 19 words
A composition according to claim 1 wherein the unsaturated N,N'-bis-imide is maleic N,N'-metaphenylene-bis-imide and the Schiff Base is 4,4'-methylenebis(N-benzylideneaniline).
Claim 9
Dependent Claim 19 words
A composition according to claim 1 wherein the unsaturated N,N'-bis-imide is maleic N,N'-metaphenylene-bis-imide and the Schiff Base is N,N'-dibenzylidene-m-phenylenediamine.
Claim 10
Dependent Claim 17 words
A composition according to claim 1 wherein the unsaturated N,N'-bis-imide maleic N,N'-diphenylmethane-bis-imide and the Schiff Base 4,4'-methylene-bis]N-(α-methylbenzylidene)aniline].
Claim 11
Dependent Claim 17 words
A solution of a composition according to claim 1 in a volatile inert solvent for said composition.
Claim 12
Dependent Claim 12 words
A molding powder consisting essentially of the composition according to claim 1.
Claim 13
Dependent Claim 23 words
The crosslinked, infusible and insoluble resin consisting essentially of the product obtained by heating at 100°C to 350°C the composition of claim 1.

References Cited (Backward Citations)

US3658764A Cited
US3669930A Cited

USPTO Annuity & Maintenance Windows

Annuity Stage Window Opens Payment Deadline Surcharge Period Until Estimated Fee Status
3.5 Years (Year 4) 1979-03-16 1979-09-15 1980-03-16 $2000.00 Window Closed / Lapsed
7.5 Years (Year 8) 1983-03-16 1983-09-15 1984-03-16 $3760.00 Window Closed / Lapsed
11.5 Years (Year 12) 1987-03-16 1987-09-15 1988-03-16 $7700.00 Window Closed / Lapsed

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