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US4847344A Expired / Lapsed US ⏱️ 0.0 years remaining

Heat-resistant maleimido copolymers

Assignee: Huntsman Advanced Materials Americas LLC
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Filing: 1988-03-10
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Granted: 1989-07-11
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Expires: 2008-03-10
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Abstract

Abstract Novel heat-resistant maleimido polymers, well adopted for the production of molded/laminated shaped articles, are copolymerizates of (a) a hydrocarbyl N,N'-bis(maleimide); (b) a diamine containing a diorganopolysiloxane bridge; optionally, (c) an N,N'-bis(maleimide) containing a diorganopolysiloxane bridge; optionally, (d) at least one other comonomer copolymerizable therewith; and, optionally, (e) a catalyst therefor.

Inventors

  • 👤 Pascal Barthelemy
  • 👤 Yves Camberlin

Bibliographic Details

Application Number —
Jurisdiction US
Data Source google_patents
Last Synchronized 2026-11-09 02:24
CPC Classifications
C; C08; C08G; C08G73/00; C08G73/06; C08G73/10; C08G73/12; C08G77/00; C08G77/42; C08G77/452; C08G77/455; C07; C07F; C07F7/00; C07F7/02; C07F7/08; C07F7/0834; C07F7/0838; C08G73/121; C08G73/122; C08G73/125; C08G73/126; C08G73/127; C08G8/00; C08G8/04; C08G8/08

Claims Analysis

Total Claims: 13
Claim 1
Independent Claim 325 words
A heat-resistant maleimido polymer comprising the copolymerizate of: (a) at least one N,N,-bis (maleimide) of the formula: ##STR25## in which the symbols Z, which may be identical or different, are each H, CH 3 or Cl; the symbol A is a cyclohexylene; phenylene; 4-methyl-1,3-phenylene; 2-methyl-1,3-phenylene; 5-methyl-1,3-phenylene; 2,5-diethyl-3-methyl-1,4-phenylene; or a radical of the formula: ##STR26## in which B is a single valence bond or a group or atom selected from ##STR27## (b) at least one diamine containing a diorganopolysiloxane bridge and having the following general formula: ##STR28## in which X, which is in the ortho, meta or para position with respect to the carbon atom of the benzene ring bonded to the nitrogen atom, is one of the following atoms or groups: ##STR29## R 1 , R 2 , R 3 , R 4 and R 5 , which may be identical or different, are each a linear or branched chain alkyl radical having from 1 to 12 carbon atoms, or a substituted such radical bearing one or more chlorine, bromine or fluorine atom substituents or a --CN group; or a phenyl radical optionally substituted with one or more alkyl and/or alkoxy radicals having from 1 to 4 carbon atoms or with one or more chlorine atoms; the symbol x ranging from 1 to 8; and the symbols y and z denote numbers, which may be identical or different, integral or fractional, the sum of which ranges from 0 to 100; (c) optionally, at least one N, N'-bis(maleimide) containing a diorganopolysiloxane bridge and having the following general formula: ##STR30## in which X, R 1 , R 2 , R 3 , R 4 , R 5 , x, y and z are as defined above; (d) optionally, at least one comonomer other than a bis (maleimide) of formula (I) or formula (III) and containing one or more copolymerizable carbon-carbon double bonds; and (e) optionally, a catalyst selected from a free-radical polymerization initiator or an imidazole compound.
Claim 2
Dependent Claim 325 words
A heat-resistant maleimido polymer comprising the copolymerizate of: (a) at least one N,N,-bis (maleimide) of the formula: ##STR25## in which the symbols Z, which may be identical or different, are each H, CH 3 or Cl; the symbol A is a cyclohexylene; phenylene; 4-methyl-1,3-phenylene; 2-methyl-1,3-phenylene; 5-methyl-1,3-phenylene; 2,5-diethyl-3-methyl-1,4-phenylene; or a radical of the formula: ##STR26## in which B is a single valence bond or a group or atom selected from ##STR27## (b) at least one diamine containing a diorganopolysiloxane bridge and having the following general formula: ##STR28## in which X, which is in the ortho, meta or para position with respect to the carbon atom of the benzene ring bonded to the nitrogen atom, is one of the following atoms or groups: ##STR29## R 1 , R 2 , R 3 , R 4 and R 5 , which may be identical or different, are each a linear or branched chain alkyl radical having from 1 to 12 carbon atoms, or a substituted such radical bearing one or more chlorine, bromine or fluorine atom substituents or a --CN group; or a phenyl radical optionally substituted with one or more alkyl and/or alkoxy radicals having from 1 to 4 carbon atoms or with one or more chlorine atoms; the symbol x ranging from 1 to 8; and the symbols y and z denote numbers, which may be identical or different, integral or fractional, the sum of which ranges from 0 to 100; (c) optionally, at least one N, N'-bis(maleimide) containing a diorganopolysiloxane bridge and having the following general formula: ##STR30## in which X, R 1 , R 2 , R 3 , R 4 , R 5 , x, y and z are as defined above; (d) optionally, at least one comonomer other than a bis (maleimide) of formula (I) or formula (III) and containing one or more copolymerizable carbon-carbon double bonds; and (e) optionally, a catalyst selected from a free-radical polymerization initiator or an imidazole compound.
Claim 3
Dependent Claim 126 words
The heat-resistant polymer as defined by claim 1, comprising at least one of the following catalysts (e): (e 1 ) a free-radical polymerization initiator; or (e 2 ) an imidazole compound of the formula: ##STR31## in which R 7 is a hydrogen atom, an alkyl or alkoxy radical having from 1 to 20 carbon atoms, or a vinyl, phenyl or nitro radical, R 8 and R 9 are the same or different and are each selected from the same radicals as R 7 or R 8 and R 9 together form, with the carbon atoms from which they depend, a single ring member, and R 6 is selected from the same radicals as R 7 or is a carbonyl group bonded to a second imidazole ring.
Claim 4
Dependent Claim 38 words
The heat-resistant polymer as defined by claim 1, comprising from 50 to 98% by weight of the bis(maleimide) (s) (a) of formula (I), and from 2 to 50% by weight of the siloxanediamine (b) of the formula (II).
Claim 5
Dependent Claim 32 words
The heat-resistant polymer as defined by claim 1 comprising from 5 to 30% by weight of bis(maleimide)-siloxane (c) of formula (III), based on the total weight of the reactants (a) + (b).
Claim 6
Dependent Claim 30 words
The heat-resistant polymer as defined by claim 1, comprising from 5 to 50 % by weight of comonomer (d), based on the total weight of the reactants (a) + (b).
Claim 7
Dependent Claim 36 words
The heat-resistant polymer as defined by claim 2, comprising from 0.01 to 1 % by weight of said catalyst (e), based on the total weight of the constituents (a) + (b) + optionally, (c) and/or (d).
Claim 8
Dependent Claim 22 words
The heat-resistant polymer as defined by claim 1, in cured state, solvent insoluble, and exhibiting essentially no softening below its decomposition temperature.
Claim 9
Dependent Claim 27 words
The heat-resistant thermosettable prepolymer comprising the copolymerizates defined in claim 1, soluble in polar organic solvents and having a softening point at a temperature below 200° C.
Claim 10
Dependent Claim 12 words
A shaped article comprising the heat-resistant polymer as define by claim 1.
Claim 11
Dependent Claim 12 words
A shaped article comprising the heat-resistant polymer as defined by claim 7.
Claim 12
Dependent Claim 12 words
A shaped article comprising the heat-resistant polymer as defined by claim 8.
Claim 13
Dependent Claim 163 words
The heat-resistant polymer as defined by claim 1, in which (d) is: (d 1 ) at least one comonomer of the formula: ##STR32## in which the allyloxy or methallyloxy radical is in the ortho, meta or para position with respect to the carbon atom of the benzene ring bonded to the nitrogen atom; or (d 2 ) a composition comprising a mixture of: (i) at least one monomer of the formula: ##STR33## in which the allyloxy or methallyloxy radical is in the ortho, meta or para position with respect to the carbon atom of the benzene ring bonded to the nitrogen atom; with: (ii) at least one monosubstituted derivative of the formula: ##STR34## and, optionally, (iii) at least one disubstituted derivative of the formula: ##STR35## or (d3) at least one substituted heterocyclic compound selected from vinyl pyridine, N-vinylpyrrolidone, allyl isocyanurate, triallyl isocyanurate and vinyl tetrahydrofuran and wherein Q in the above formulae (III), (IV), (V) and (VI) is --H or --CH 3 .

References Cited (Backward Citations)

US4544728A Cited
US4656235A Cited

USPTO Annuity & Maintenance Windows

Annuity Stage Window Opens Payment Deadline Surcharge Period Until Estimated Fee Status
3.5 Years (Year 4) 1992-07-10 1993-01-09 1993-07-11 $2000.00 Window Closed / Lapsed
7.5 Years (Year 8) 1996-07-10 1997-01-09 1997-07-11 $3760.00 Window Closed / Lapsed
11.5 Years (Year 12) 2000-07-10 2001-01-09 2001-07-11 $7700.00 Window Closed / Lapsed

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