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US4966923A Expired / Lapsed US ⏱️ 0.0 years remaining

Polymerizable compositions

Assignee: Novartis Corp
•
Filing: 1987-11-13
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Granted: 1990-10-30
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Expires: 2007-11-13
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Abstract

Abstract A polymerizable composition comprises a mixture of (A) a substance having at least one allyl- or methallyl-substituted bicyclo[2.2.1]-hept-5-ene-2,3-dicarboxylic acid imide residue, and (B) a substance having at least one polymerizable residue of formula CH.sub.2 =C(R.sup.1)COO-- I where R 1 denotes a hydrogen atom or a methyl group. Typically, (A) is bis[4-(allylbicyclo[2.2.1]hept-5-ene-2,3-dicarboximidophenyl)]methane and (B) is an acrylate or methacrylate of a polyhydric alcohol. The compositions can be photopolymerized or heat-cured. They are suitable for use in prepreg manufacture and in image formation.

Inventors

  • 👤 Christopher P. Banks
  • 👤 Edward Irving
  • 👤 Alfred Renner
  • 👤 Terence J. Smith

Bibliographic Details

Application Number —
Jurisdiction US
Data Source google_patents
Last Synchronized 2026-10-27 12:24
CPC Classifications
G; G03; G03F; G03F7/00; G03F7/004; G03F7/027; C; C07; C07D; C07D209/00; C07D209/56; C07D209/58; C07D209/72; C07D209/76; C08; C08F; C08F226/00; C08F226/06; C08J; C08J5/00; C08J5/24; C08J5/241; C08J5/243; C08J5/249

Claims Analysis

Total Claims: 13
Claim 1
Independent Claim 387 words
A polymerizable composition comprising a mixture of (A) a substance having at least one allyl- or methallyl-substituted bicyclo[2.2.1]-hept-5-ene-2,3-dicarboxylic acid imide residue and having formula III ##STR9## where n denotes 1, 2 or 3, R 2 denotes allyl or methallyl, R 3 denotes a hydrogen atom or methyl group, and when n is 1, R 4 denotes a hydrogen atom, a hydroxyl group, or an organic group selected from C 1 -C 40 -alkyl, C 1 -C 40 -alkyl interrupted in the chain by oxygen atoms, C 3 -C 6 -alkenyl, C 5 -C 20 -cycloalkyl, C 6 -C 20 -aryl or benzyl, any of said organic groups being substituted or unsubstituted by a hydroxyl group, or a group of formula IV --Ar.sup.1 --X--Ar.sup.2 --OH IV where Ar 1 and Ar 2 each denote a phenylene group and X denotes methylene, isopropylidene, --CO--, --O--, --S-- --SO 2 --, or when n is 2, R 4 denotes C 2 -C 20 -alkylene, C 2 -C 20 -alkylene interrupted in the chain by oxygen atoms or secondary amino groups, C 6 -C 20 -arylene or a group of formula V --Ar.sup.1 --X--Ar.sup.2 -- V where Ar 1 , Ar 2 and X are as defined in formula IV, or when n is 3, R 4 denotes a group of formula VI ##STR10## Y denotes >P═O or >P-- and R denotes an alkylene group of 2 to 40 carbon atoms, C 2 -C 40 -alkylene in the chain by oxygen atoms, a m-or p-phenylene group, or a m- or p-phenyleneoxy group in which the oxygen atom is bonded to the group Y, or Y denote >CH-- and R denotes a m- or p-phenylene group, or Y denotes CH 3 CH 2 C(CH 2 ) 3 or --CH 2 CHCH 2 -- and R denotes an oxyalkylene group of 2 or 3 carbon atoms, a polyoxyethylene or polyoxypropylene group of 4 to 40 carbon atoms, or a m- or p-phenyleneoxy group in which the oxygen atom it attached to the group Y, or Y denotes N- and R denotes an alkylene group of 2 to 10 carbon atoms, or a m- or p-phenylene group, and (B) an acrylic material having at least one polymerizable residue of formula I CH.sub.2 ═C(R.sup.1)COO-- I where R 1 denotes a hydrogen atom or a methyl group.
Claim 2
Dependent Claim 387 words
A polymerizable composition comprising a mixture of (A) a substance having at least one allyl- or methallyl-substituted bicyclo[2.2.1]-hept-5-ene-2,3-dicarboxylic acid imide residue and having formula III ##STR9## where n denotes 1, 2 or 3, R 2 denotes allyl or methallyl, R 3 denotes a hydrogen atom or methyl group, and when n is 1, R 4 denotes a hydrogen atom, a hydroxyl group, or an organic group selected from C 1 -C 40 -alkyl, C 1 -C 40 -alkyl interrupted in the chain by oxygen atoms, C 3 -C 6 -alkenyl, C 5 -C 20 -cycloalkyl, C 6 -C 20 -aryl or benzyl, any of said organic groups being substituted or unsubstituted by a hydroxyl group, or a group of formula IV --Ar.sup.1 --X--Ar.sup.2 --OH IV where Ar 1 and Ar 2 each denote a phenylene group and X denotes methylene, isopropylidene, --CO--, --O--, --S-- --SO 2 --, or when n is 2, R 4 denotes C 2 -C 20 -alkylene, C 2 -C 20 -alkylene interrupted in the chain by oxygen atoms or secondary amino groups, C 6 -C 20 -arylene or a group of formula V --Ar.sup.1 --X--Ar.sup.2 -- V where Ar 1 , Ar 2 and X are as defined in formula IV, or when n is 3, R 4 denotes a group of formula VI ##STR10## Y denotes >P═O or >P-- and R denotes an alkylene group of 2 to 40 carbon atoms, C 2 -C 40 -alkylene in the chain by oxygen atoms, a m-or p-phenylene group, or a m- or p-phenyleneoxy group in which the oxygen atom is bonded to the group Y, or Y denote >CH-- and R denotes a m- or p-phenylene group, or Y denotes CH 3 CH 2 C(CH 2 ) 3 or --CH 2 CHCH 2 -- and R denotes an oxyalkylene group of 2 or 3 carbon atoms, a polyoxyethylene or polyoxypropylene group of 4 to 40 carbon atoms, or a m- or p-phenyleneoxy group in which the oxygen atom it attached to the group Y, or Y denotes N- and R denotes an alkylene group of 2 to 10 carbon atoms, or a m- or p-phenylene group, and (B) an acrylic material having at least one polymerizable residue of formula I CH.sub.2 ═C(R.sup.1)COO-- I where R 1 denotes a hydrogen atom or a methyl group.
Claim 3
Dependent Claim 19 words
A composition according to claim 1, in which R 2 denotes allyl and R 3 denotes a hydrogen atom.
Claim 4
Dependent Claim 234 words
A composition according to claim 1, in which n is 1 and R 4 denotes a hydrogen atom, a hydroxyl group, C 1 -C 8 alkyl, allyl, cyclohexyl, phenyl or benzyl, C 2 -C 8 alkyl substituted by one or two hydroxyl groups and interrupted or uninterrupted in the chain by 1 to 3 oxygen atoms, hydroxycyclohexyl, hydroxyphenyl, or a group of formula IV where X denotes methylene, isopropylidene, --O--, or --SO 2 --, or n is 2 and R 4 denotes C 2 -C 12 straight chain alkylene, m- or p-phenylene or a group of formula V where X denotes methylene, --O-- or --SO 2 --, or n is 3 and R 4 denotes a group of formula VI where Y denotes >P═O or >P-- and R denotes an alkylene group of 2 to 4 carbon atoms, a m- or p-phenylene group or a m-or p-phenyleneoxy group, or Y denotes >CH-- and R denotes a p-phenylene group, or Y denotes CH 3 CH 2 C(CH 2 ) 3 and R denotes a group --[CH 2 CH(CH 3 )O]-- r where r is 1, 2 or 3, or Y denotes --CH 2 CHCH 2 -- and R denotes a group --(CH 2 CH 2 O)-- r where r is 1, 2 or 3, or a m- or p-phenyleneoxy group, or Y denotes >N-- and R denotes an ethylene, trimethylene, or m- or p-phenylene group.
Claim 5
Dependent Claim 56 words
A composition according to claim 3, in which R 2 denotes allyl, R 3 denotes a hydrogen atom and n is 1 and R 4 denotes a hydroxyl group, allyl, 2-hydroxyethyl, or p-hydroxyphenyl, or n is 2 and R 4 denotes --(CH 2 ) 6 --, ##STR11## or n is 3 and R 4 denotes ##STR12##
Claim 6
Dependent Claim 34 words
A composition according to claim 1, in which the acrylic material is an ester of a carboxylic acid containing a group of formula I and a polyhydric alcohol or phenol or an epoxide resin.
Claim 7
Dependent Claim 40 words
A composition according to claim 5, in which the acrylic material is a polyacrylate or polymethacrylate ester of a polyhydric alcohol having from 2 to 10 alcoholic hydroxyl groups or of a polyglycidyl ether of a polyhydric alcohol or phenol.
Claim 8
Dependent Claim 16 words
A composition according to claim 1, which also contains (C) a photopolymerization initiator for acrylic materials.
Claim 9
Dependent Claim 16 words
A composition according to claim 1, which also contains (D) a thermally activated cationic polymerization initiator.
Claim 10
Dependent Claim 122 words
A composition according to claim 8, in which (D) is an imide of formula ##STR13## where R 2 denotes allyl or methallyl, R 3 denotes a hydrogen atom or a methyl group, R 5 denotes a valency bond, a C 2 -C 20 alkylene radical interrupted or uninterrupted in the chain by oxygen atoms, a C 5 -C 20 cycloalkylene radical, a C 6 -C 20 arylene radical or a group of formula V --Ar.sup.1 --X--Ar.sup.2 -- V where Ar 1 and Ar 2 each denote a phenylene group and X denotes methylene, isopropylidene, --CO--, --O--, --S--, or --SO 2 --, and R 6 denotes C 1 -C 12 alkyl, C 5 -C 8 cycloalkyl, C 6 -C 12 aryl or benzyl.
Claim 11
Dependent Claim 26 words
A composition according to claim 1, in which (B) is present in an amount 10 to 80% by weight of the mixture of (A) and (B).
Claim 12
Dependent Claim 12 words
A composition according to claim 1 photopolymerized by exposure to actinic radiation.
Claim 13
Dependent Claim 9 words
A compostion according to claim 1 cured by heating.

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