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US4066609A Expired / Lapsed US ⏱️ 0.0 years remaining

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

Assignee: Novartis Corp
•
Filing: 1976-01-26
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Granted: 1978-01-03
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Expires: 1996-01-26
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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 2026-11-05 22:34
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: 12
Claim 1
Independent Claim 506 words
A glass fabric or fiber impregnated with a composition comprising a. an unsaturated N,N'-bis-imide having the formula ##STR12## 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 ##STR13## wherein W 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 ##STR14## where Y is a covalent bond or -NH, and R 8 is phenyl, piperidino, hydrogen, diphenylamino or di(lower)alkyl amino; D is a divalent radical containing olefinic unsaturation having the formula ##STR15## wherein R 3 is hydrogen, methyl, bromo or chloro; R 4 is hydrogen, methyl, bromo or chloro; and b. from about 0.5 to 0.166 mole equivalents per mole equivalent of (a) of a Schiff base having the formula ##STR16## 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 from 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; ; R 3 is 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, cyclohexyl or cyclopentyl; R 4 is an alkylene group containing from 2 to 12 carbon atoms, phenylene, tolylene, biphenylene, naphthylene, or an arylene group having the formula ##STR17## wherein X is, -S-, -O-, NH, N-phenyl, sulfonyl, or an alkylene group containing from 1 to 3 carbon atoms; 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 ##STR18## wherein W 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 ##STR19## 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 506 words
A glass fabric or fiber impregnated with a composition comprising a. an unsaturated N,N'-bis-imide having the formula ##STR12## 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 ##STR13## wherein W 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 ##STR14## where Y is a covalent bond or -NH, and R 8 is phenyl, piperidino, hydrogen, diphenylamino or di(lower)alkyl amino; D is a divalent radical containing olefinic unsaturation having the formula ##STR15## wherein R 3 is hydrogen, methyl, bromo or chloro; R 4 is hydrogen, methyl, bromo or chloro; and b. from about 0.5 to 0.166 mole equivalents per mole equivalent of (a) of a Schiff base having the formula ##STR16## 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 from 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; ; R 3 is 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, cyclohexyl or cyclopentyl; R 4 is an alkylene group containing from 2 to 12 carbon atoms, phenylene, tolylene, biphenylene, naphthylene, or an arylene group having the formula ##STR17## wherein X is, -S-, -O-, NH, N-phenyl, sulfonyl, or an alkylene group containing from 1 to 3 carbon atoms; 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 ##STR18## wherein W 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 ##STR19## 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 15 words
A fabric or fiber according to claim 1 which further contains a peroxide curing agent.
Claim 4
Dependent Claim 317 words
A fabric or fiber according to claim 1 wherein (a) is an unsaturated N,N'-bis-imide having the formula ##STR20## wherein A is m or p-phenylene, biphenylene or alkylene group containing from 2 to 12 carbon atoms or a group having the formula ##STR21## wherein X is -O-, sulfonyl, or alkylene group containing from 1 to 3 carbon atoms; and D is a divalent radical containing olefinic unsaturation having the formula ##STR22## wherein R 3 is hydrogen or methyl; and b. is a Schiff base having the formula ##STR23## wherein R 1 and R 2 independently is hydrogen, an alkyl group containing from 1 to 12 carbon atoms, phenyl, 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; R 3 is alkyl group containing from 1 to 12 carbon atoms, phenyl, tolyl, chlorophenyl, or alkoxyphenyl, said alkoxy containing from 1 to 5 carbon atoms; R 4 is alkylene containing from 2 to 12 carbon atoms, phenylene, tolylene, biphenylene, or a group having the formula ##STR24## wherein X is O, sulfonyl or alkylene containing from 1 to 3 carbon atoms; 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 ##STR25## wherein W 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 ##STR26## 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 21 words
A fabric or fiber according to claim 1 wherein the unsaturated N,N'-bis-imide is maleic N,N'-diphenylmethanebis-imide, and the Schiff Base is 4,4'-methylenebis[N-(α-methylbenzylidene)aniline].
Claim 6
Dependent Claim 21 words
A fabric or fiber according to claim 1 wherein the unsaturated N,N'-bis-imide is maleic N,N'-diphenylmethanebis-imide and the Schiff Base is N,N'-dibenzylidene-metaphenylenediamine.
Claim 7
Dependent Claim 21 words
A fabric or fiber according to claim 1 wherein the unsaturated N,N'-bis-imide is maleic N,N'-diphenylmethanebis-imide and the Schiff Base is 4,4'methylenebis(N-benzylideneaniline).
Claim 8
Dependent Claim 21 words
A fabric or fiber according to claim 1 wherein the unsaturated N,N'-bis-imide is maleic N,N'-metaphenylenebis-imide and the Schiff Base is 4,4'methylenebis(N-benzylideneaniline).
Claim 9
Dependent Claim 21 words
A fabric or fiber according to claim 1 wherein the unsaturated N,N'-bis-imide is maleic N,N'-metaphenylenebis-imide and the Schiff Base is N,N'-dibenzylidene-m-phenylenediamine.
Claim 10
Dependent Claim 21 words
A fabric or fiber according to claim 1 wherein the unsaturated N,N'-bis-imide is maleic N,N'-diphenylmethanebis-imide and the Schiff Base is 4,4'-methylene-bis[N-(α-methybenzylidene)aniline].
Claim 11
Dependent Claim 14 words
A laminate consisting essentially of the impregnated fabric or fiber according to claim 1.
Claim 12
Dependent Claim 23 words
The crosslinked, infusible and insoluble product obtained by heating at 100° C to 350° C the impregnated fabric or fiber of claim 1.

References Cited (Backward Citations)

US3910859A Cited
US3929687A Cited

USPTO Annuity & Maintenance Windows

Annuity Stage Window Opens Payment Deadline Surcharge Period Until Estimated Fee Status
3.5 Years (Year 4) 1981-01-02 1981-07-04 1982-01-03 $2000.00 Window Closed / Lapsed
7.5 Years (Year 8) 1985-01-02 1985-07-04 1986-01-03 $3760.00 Window Closed / Lapsed
11.5 Years (Year 12) 1989-01-02 1989-07-04 1990-01-03 $7700.00 Window Closed / Lapsed

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