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US4105646A Expired / Lapsed US ⏱️ 0.0 years remaining

α,β-Unsaturated schiff-base chain extension reactions for high temperature polymers

Assignee: BASF Corp
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Filing: 1976-09-03
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Granted: 1978-08-08
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Expires: 1996-09-03
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Abstract

Abstract This invention provides compositions containing thermally stable prepolymers with azadiene end groups, and compositions containing such prepolymers in combination with dienophiles and the chain-extended and cross-linked polymers obtained from these systems. The combination of such prepolymers with dienophiles facilitates processing of the prepolymer resin by lowering the softening and curing temperatures under processing conditions.

Inventors

  • 👤 Roland A. E. Winter

Bibliographic Details

Application Number —
Jurisdiction US
Data Source google_patents
Last Synchronized 2026-11-05 21:35
CPC Classifications
C; C08; C08G; C08G73/00; C08G73/06; C08G73/10; C08G73/12; Y; Y10; Y10S; Y10S525/00; Y10S525/925; Y10S525/928; Y10T; Y10T428/00; Y10T428/31504; Y10T428/31551; Y10T428/31623

Claims Analysis

Total Claims: 11
Claim 1
Independent Claim 304 words
A composition of matter consisting essentially of (a) a compound of the formula ##STR45## wherein a is a number from 0.1 to 2, R 1 , R 2 , R 3 and R 4 are independently hydrogen or a monovalent aliphatic, cycloaliphatic or aromatic radical or a combination of such radicals, and R 5 is a divalent organic radical containing from 2 to 30 carbon atoms and selected from the group consisting of aromatic, aliphatic, alkylaromatic and cycloaliphatic radicals combinations of these, and radicals with hetero-atom containing bridging groups where the hetero-atom in the bridge is selected from the group consisting of oxygen, sulfur, nitrogen, phosphorus and silicon, and (b) from about 1 to 10 mole equivalents per mole equivalent of (a) of a bis-dienophile selected from the group consisting of (1) a compound of the formula ##STR46## (2) a polyamide-acid of the formula ##STR47## its corresponding polyimide, (3) a polyamide-amide acid of the formula ##STR48## its corresponding polyamide-imide, and (4) a polyamide-amide acid of the formula ##STR49## and its corresponding polyamide-imide, wherein R 5 and R 7 are the same or different and each is defined as R 5 above, R 6 is a tetravalent aliphatic, cycloaliphatic, aromatic or heterocyclic radical containing at least 2 carbon atoms or a combination of aromatic and aliphatic radicals, m is a number from 1 to 20, and D is a divalent radical containing olefinic unsaturation selected from a group having the formula ##STR50## wherein R 16 is hydrogen, methyl, bromo or chloro; R 17 is hydrogen, bromo or chloro; Y 1 -y 6 inclusive is selected from the group consisting of hydrogen, bromine, chlorine, nitro, phenyl, and alkyl of from 1 to 6 carbon atoms; and X is carbonyl, oxygen, sulfur, chloro or bromo substituted methylene, alkylidene of from 1 to 6 carbon atoms, and benzylidene.
Claim 2
Dependent Claim 304 words
A composition of matter consisting essentially of (a) a compound of the formula ##STR45## wherein a is a number from 0.1 to 2, R 1 , R 2 , R 3 and R 4 are independently hydrogen or a monovalent aliphatic, cycloaliphatic or aromatic radical or a combination of such radicals, and R 5 is a divalent organic radical containing from 2 to 30 carbon atoms and selected from the group consisting of aromatic, aliphatic, alkylaromatic and cycloaliphatic radicals combinations of these, and radicals with hetero-atom containing bridging groups where the hetero-atom in the bridge is selected from the group consisting of oxygen, sulfur, nitrogen, phosphorus and silicon, and (b) from about 1 to 10 mole equivalents per mole equivalent of (a) of a bis-dienophile selected from the group consisting of (1) a compound of the formula ##STR46## (2) a polyamide-acid of the formula ##STR47## its corresponding polyimide, (3) a polyamide-amide acid of the formula ##STR48## its corresponding polyamide-imide, and (4) a polyamide-amide acid of the formula ##STR49## and its corresponding polyamide-imide, wherein R 5 and R 7 are the same or different and each is defined as R 5 above, R 6 is a tetravalent aliphatic, cycloaliphatic, aromatic or heterocyclic radical containing at least 2 carbon atoms or a combination of aromatic and aliphatic radicals, m is a number from 1 to 20, and D is a divalent radical containing olefinic unsaturation selected from a group having the formula ##STR50## wherein R 16 is hydrogen, methyl, bromo or chloro; R 17 is hydrogen, bromo or chloro; Y 1 -y 6 inclusive is selected from the group consisting of hydrogen, bromine, chlorine, nitro, phenyl, and alkyl of from 1 to 6 carbon atoms; and X is carbonyl, oxygen, sulfur, chloro or bromo substituted methylene, alkylidene of from 1 to 6 carbon atoms, and benzylidene.
Claim 3
Dependent Claim 209 words
A composition according to claim 1 where in the compound of formula I and in the bis-dienophile R 5 and R 7 are the same or different and each is an alkylene group containing from 2 to 12 carbon atoms, a cycloalkylene group containing from 4 to 6 carbon atoms; a xylylene group, an arylene group selected from ortho, meta or para phenylene, xylylene, tolylene, biphenylene, naphthylene or anthrylene; a substituted arylene group of the formula ##STR51## wherein W is a covalent bond, sulfur, carbonyl, --NH, --N--(lower)alkyl, O, S, SS, --N-phenyl, sulfonyl, a linear or branched alkylene group of from 1 to 3 carbon atoms, ##STR52## arylene, a dialkyl or diaryl silyl group, ##STR53## (lower) alkyl, said lower alkyl containing from 1 to 5 carbon atoms, --N═N--, or ##STR54## R 8 and R 9 are independent and each is hydrogen, halogen, lower alkyl from 1 to 5 carbon atoms, lower alkoxy containing from 1 to 5 carbon atoms, aryl, a group having the formula ##STR55## wherein R 11 is hydrogen, halogen or lower alkyl of from 1 to 5 carbon atoms, or a group having the formula ##STR56## wherein Y is a covalent bond or NH-- and R 10 is phenyl, piperidino, H, diphenylamino, or a di(lower alkyl)amino group.
Claim 4
Dependent Claim 38 words
A composition according to claim 2 wherein the bis-dienophile is selected from the group consisting of (1) a compound of the formula ##STR57## (2) a polyamide-acid of the formula ##STR58## and (3) a polyimide of the formula ##STR59##
Claim 5
Dependent Claim 72 words
A composition according to claim 2 where (a) in the compound of formula I R 1 is hydrogen or phenyl, R 2 and R 3 are hydrogen, R 4 is phenyl, and R 5 is selected from the group consisting of ##STR60## and (b) the bis-dienophile is the compound of the formula ##STR61## wherein R 5 is as defined under clause (a) above, and D is a group of the formula ##STR62##
Claim 6
Dependent Claim 16 words
A solution of a composition according to claim 1 in a volatile solvent for said composition.
Claim 7
Dependent Claim 12 words
A molding powder consisting essentially of the composition according to claim 1.
Claim 8
Dependent Claim 16 words
A composition according to claim 2 wherein the bis-dienophile is the compound of the formula ##STR63##
Claim 9
Dependent Claim 17 words
The crosslinked resin obtained by heating at 100° to 250° C, the composition according to claim 1.
Claim 10
Dependent Claim 60 words
A composition according to claim 4 where (a) is the compound of formula I R 1 , r 2 and R 3 are hydrogen, R 4 is phenyl, R 5 is a group of the formula ##STR64## and (b) in the bis-dienophile R 5 is a group of the formula ##STR65## and D is a group of the formula ##STR66##
Claim 11
Dependent Claim 13 words
A glass fabric or fiber impregnated with the composition according to claim 1.

References Cited (Backward Citations)

US3432574A Cited
US3843602A Cited
US3845018A Cited

USPTO Annuity & Maintenance Windows

Annuity Stage Window Opens Payment Deadline Surcharge Period Until Estimated Fee Status
3.5 Years (Year 4) 1981-08-07 1982-02-06 1982-08-08 $2000.00 Window Closed / Lapsed
7.5 Years (Year 8) 1985-08-07 1986-02-06 1986-08-08 $3760.00 Window Closed / Lapsed
11.5 Years (Year 12) 1989-08-07 1990-02-06 1990-08-08 $7700.00 Window Closed / Lapsed

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