Crosslinkable polymers of unsaturated imides

Claim 2

A crosslinkable polymer which has an average molecular weight of at least 1,200, or the corresponding cyclized imide derivative, which is manufactured by reacting at a temperature between about -50° and 300° C. in the melt or in an inert organic solvent or solvent mixture

Claim 3

5 to 100 mol% of a compound of the formula Ib or IIb ##STR20## and 0 to 99.5 mol% of a compound of the formula IV ##STR21## with substantially stoichiometric amounts of a compound of the formula V HY--Q--XH in which formulae m and n independently of one another represent the number 1 or 2, A represents a radical of the formula ##STR22## R 2 ' represents phenoxy; phenoxy substituted by one or two nitro groups, by one alkyl of 1 to 2 carbon atoms, by one alkoxy of 1 to 2 carbon atoms or by two to five halogen atoms; alkoxy with 1 to 18 carbon atoms or the two R 2 's conjointly represent the --O-- grouping, R' 1 represents a chlorine atom, phenoxy; phenoxy substituted by one or two nitro groups, by one alkyl of 1 to 2 carbon atoms, by one alkoxy of 1 to 2 carbon atoms or by two to five halogen atoms; or alkoxy of 1 to 18 carbon atoms, R 3 and R 4 independently of one another represent hydrogen, chlorine or bromine, X and Y represent --O-- or one of X and Y represents --O-- and the other denotes ##STR23## where R 5 represents hydrogen, alkyl with 1-4 carbon atoms or phenyl, Q represents an aliphatic radical with at least 2 carbon atoms or a cycloaliphatic, araliphatic, carbocyclic-aromatic or heterocyclic-aromatic radical, and Q 1 represents an aliphatic radical or a cycloaliphatic, carbocyclic-aromatic or heterocyclic-aromatic radical, in which the carbonyl and carboxyl groups are bonded to different carbon atoms and the carboxyl groups are each in the ortho-position relative to a carbonyl group, M 1 represents a chlorine atom, a hydroxyl group, phenoxy; phenoxy substituted by one or two nitro groups, by one alkyl of 1 to 2 carbon atoms, by one alkoxy of 1 to 2 carbon atoms or by two to five halogen atoms; or alkoxy with 1 to 18 carbon atoms, or when m or n is 2, M 1 , conjointly with M 2 , forms the --O-- grouping and the groups --COM 1 and --COM 2 are bonded to different carbon atoms and the --COM 1 groups are each in the ortho-position relative to a --COM 2 group.

Claim 4

5 to 100 mol% of a compound of the formula Ib or IIb ##STR20## and 0 to 99.5 mol% of a compound of the formula IV ##STR21## with substantially stoichiometric amounts of a compound of the formula V HY--Q--XH in which formulae m and n independently of one another represent the number 1 or 2, A represents a radical of the formula ##STR22## R 2 ' represents phenoxy; phenoxy substituted by one or two nitro groups, by one alkyl of 1 to 2 carbon atoms, by one alkoxy of 1 to 2 carbon atoms or by two to five halogen atoms; alkoxy with 1 to 18 carbon atoms or the two R 2 's conjointly represent the --O-- grouping, R' 1 represents a chlorine atom, phenoxy; phenoxy substituted by one or two nitro groups, by one alkyl of 1 to 2 carbon atoms, by one alkoxy of 1 to 2 carbon atoms or by two to five halogen atoms; or alkoxy of 1 to 18 carbon atoms, R 3 and R 4 independently of one another represent hydrogen, chlorine or bromine, X and Y represent --O-- or one of X and Y represents --O-- and the other denotes ##STR23## where R 5 represents hydrogen, alkyl with 1-4 carbon atoms or phenyl, Q represents an aliphatic radical with at least 2 carbon atoms or a cycloaliphatic, araliphatic, carbocyclic-aromatic or heterocyclic-aromatic radical, and Q 1 represents an aliphatic radical or a cycloaliphatic, carbocyclic-aromatic or heterocyclic-aromatic radical, in which the carbonyl and carboxyl groups are bonded to different carbon atoms and the carboxyl groups are each in the ortho-position relative to a carbonyl group, M 1 represents a chlorine atom, a hydroxyl group, phenoxy; phenoxy substituted by one or two nitro groups, by one alkyl of 1 to 2 carbon atoms, by one alkoxy of 1 to 2 carbon atoms or by two to five halogen atoms; or alkoxy with 1 to 18 carbon atoms, or when m or n is 2, M 1 , conjointly with M 2 , forms the --O-- grouping and the groups --COM 1 and --COM 2 are bonded to different carbon atoms and the --COM 1 groups are each in the ortho-position relative to a --COM 2 group.

Claim 5

A crosslinkable polymer according to claim 1 which is manufactured by using a compound of the formula Ib or IIb wherein A represents the group ##STR24## or the --CH═CH-- group.

Claim 6

A crosslinkable polymer which has an average molecular weight of at least 1,200, which is manufactured by reacting at a temperature between about 30°-100° C. in bulk, solution, precipitation, emulsion or suspension polymerization in the presence of 0.01 to 5% by weight based on the total weight of monomers, of a free-rdical initiator 0.5 to 100 mol % of a compound of the formula Ia or IIa ##STR25## with 0 to 99.5 mol % of a compound of the formula III ##STR26## A represents a radical of the formula ##STR27## R 2 represents hydroxyl, phenoxy; phenoxy substituted by one or two nitro groups, by one alkyl of 1 to 2 carbon atoms, by one alkoxy of 1 to 2 carbon atoms or by two to five halogen atoms; alkoxy with 1 to 18 carbon atoms or an --O--M + group, or the two R 2 s conjointly represent the --O-- grouping, R 1 represents a hydroxyl group, phenoxy; phenoxy substituted by one or two nitro groups, by one alkyl of 1 to 2 carbon atoms, by one alkoxy of 1 to 2 carbon atoms or by two to five halogen atoms; alkoxy of 1 to 18 carbon atoms or --O--M + , with the proviso that when R 2 is hydroxyl, R 1 cannot be --O--M + , and with the proviso that when R 2 is --O--M + , R 1 cannot be hydroxyl, and M + represents an alkali metal cation, a trialkylammonium cation with 3-24 carbon atoms or a quaternary ammonium cation, R 3 and R 4 independently of one another represent hydrogen, chlorine or bromine, and Z 1 and Z 3 each represent hydrogen, Z 2 represents hydrogen, chlorine or methyl and Z 4 represents hydrogen, methyl, ethyl, chlorine, --CN, --COOH, --CONH 2 , phenyl, methylphenyl, methoxyphenyl, cyclohexyl, pyridyl, imidazolyl, pyrrolidonyl, --COO--alkyl with 1-12 carbon atoms in the alkyl part, --COO--phenyl, ##STR28## --COO--alkyl--OH with 1-3 carbon atoms in the alkyl part or ##STR29## wherein R 8 denotes a linear or branched saturated aliphatic radical with at most 10 carbon atoms, R 9 denotes hydrogen or methyl and x denotes an integer from 1 to 3; --OCO--alkyl with 1-4 carbon atoms in the alkyl part, --OCO--phenyl, --CO--alkyl with 1-3 carbon atoms in the alkyl part, alkoxy with 1-6 carbon atoms, phenoxy, --CH═CH 2 or ##STR30## or Z 1 and Z 2 each represent hydrogen and Z 3 and Z 4 conjointly form the ##STR31##

Claim 7

A crosslinkable polymer which has an average molecular weight of at least 1,200, which is manufactured by reacting at a temperature between about 30°-100° C. in bulk, solution, precipitation, emulsion or suspension polymerization in the presence of 0.01 to 5% by weight based on the total weight of monomers, of a free-rdical initiator 0.5 to 100 mol % of a compound of the formula Ia or IIa ##STR25## with 0 to 99.5 mol % of a compound of the formula III ##STR26## A represents a radical of the formula ##STR27## R 2 represents hydroxyl, phenoxy; phenoxy substituted by one or two nitro groups, by one alkyl of 1 to 2 carbon atoms, by one alkoxy of 1 to 2 carbon atoms or by two to five halogen atoms; alkoxy with 1 to 18 carbon atoms or an --O--M + group, or the two R 2 s conjointly represent the --O-- grouping, R 1 represents a hydroxyl group, phenoxy; phenoxy substituted by one or two nitro groups, by one alkyl of 1 to 2 carbon atoms, by one alkoxy of 1 to 2 carbon atoms or by two to five halogen atoms; alkoxy of 1 to 18 carbon atoms or --O--M + , with the proviso that when R 2 is hydroxyl, R 1 cannot be --O--M + , and with the proviso that when R 2 is --O--M + , R 1 cannot be hydroxyl, and M + represents an alkali metal cation, a trialkylammonium cation with 3-24 carbon atoms or a quaternary ammonium cation, R 3 and R 4 independently of one another represent hydrogen, chlorine or bromine, and Z 1 and Z 3 each represent hydrogen, Z 2 represents hydrogen, chlorine or methyl and Z 4 represents hydrogen, methyl, ethyl, chlorine, --CN, --COOH, --CONH 2 , phenyl, methylphenyl, methoxyphenyl, cyclohexyl, pyridyl, imidazolyl, pyrrolidonyl, --COO--alkyl with 1-12 carbon atoms in the alkyl part, --COO--phenyl, ##STR28## --COO--alkyl--OH with 1-3 carbon atoms in the alkyl part or ##STR29## wherein R 8 denotes a linear or branched saturated aliphatic radical with at most 10 carbon atoms, R 9 denotes hydrogen or methyl and x denotes an integer from 1 to 3; --OCO--alkyl with 1-4 carbon atoms in the alkyl part, --OCO--phenyl, --CO--alkyl with 1-3 carbon atoms in the alkyl part, alkoxy with 1-6 carbon atoms, phenoxy, --CH═CH 2 or ##STR30## or Z 1 and Z 2 each represent hydrogen and Z 3 and Z 4 conjointly form the ##STR31##

Claim 8

Crosslinkable polymers according to claim 3, which is manufactured by using 50-99 mol % of a compound of the formula III, wherein Z 1 and Z 3 each denote hydrogen, Z 2 denotes hydrogen or methyl and Z 4 denotes --COO--alkyl with 1-10 carbon atoms in the alkyl part, or Z 1 , Z 2 and Z 3 each denote hydrogen and Z 4 denotes --CN, chlorine, phenyl or --OCOCH 3 .

Claim 9

A crosslinkable polymer according to claim 1, which is manufactured by using 3-50 mol % of a compound of the formula Ib, wherein A represents the --CH═CH-- group, R 1 ' represents a chlorine atom or an alkoxy group with 1-4 carbon atoms and the two R 2 's conjointly represent the --O-- grouping.

Claim 10

A crosslinkable polymer according to claim 1, which is manufactured by using a compound of the formula V and 50-97 mol % of a compound of the formula IV, in which formulae one of X and Y denotes --O-- and the other denotes --NH--, Q denotes the 1,3- or 1,4-phenylene group, m and n denote the number 1, the M 1 s each denote a chlorine atom and Q 1 denotes the 1,3- or 1,4-phenylene group.

Claim 11

A crosslinkable polymer according to claim 1, which is manufactured by using a compound of the formula V and 50-97 mol % of a compound of the formula IV, in which formulae X and Y each denote --O--, Q denotes an unsubstituted alkylene group with 2-12 carbon atoms, m and n denote the number 1, and M 1 s each denote a chlorine atom and Q 1 denotes a 1,3- or 1,4-phenylene group.

Claim 12

A crosslinkable polymer according to claim 1, which is manufactured by reacting about 50 mol % of 5-maleimidyltrimellitic anhydride-chloride and about 50 mol % of isophthalic acid dichloride with 3-aminophenol.

Claim 13

A crosslinkable polymer according to claim 1 wherein A is --CH═CH--.

Claim 14

A crosslinkable polymer according to claim 3, which is manufactured by using 1-50 mol % of a compound of the formula Ia, wherein A represents the --CH═CH-- group, R 1 represents --OH or an alkoxy group with 1-4 carbon atoms and the two R 2 s conjointly represent the --O-- grouping.

Claim 15

A crosslinkable polymer according to claim 3 which is manufactured by using a compound of formula Ia or IIa wherein A represents the group ##STR32## or the --CH═CH-- group.

Claim 16

A crosslinkable polymer according to claim 3 wherein A is --CH═CH--.

Claim 17

A crosslinkable polymer according to claim 3 wherein the compound of formula Ia is 5-maleimidyl-trimellitic anhydride ethyl ester and the compound of formula III is styrene.

Claim 18

A crosslinkable polymer according to claim 1, which is manufactured by reacting about 10 mol % of 5-maleimidyltrimellitic anhydride-chloride and about 90 mol % of isophthalic acid dichloride with butanediol.