Maleimide: aryloxy diamine resin composition and process for producing same

Claim 2

A maleimide resin composition comprising a maleimide-diamine adduct having the recurring units: ##STR13## wherein A represents a mono- , di-, tri-or tetravalent organic group containing at least two carbon atoms, m represents an integer of 0 ro 4, R 1 through R 4 which are the same or different represent hydrogen atom, a lower alkyl group, a lower alkoxy group, chlorine atom or bromine atom, and R 5 and R 6 which are the same or different represent hydrogen atom, methyl group, ethyl group, trifluoromethyl group or trichloromethyl group, said adduct being soluble in an organic solvent having a boiling point of 130° C. or lower to form a solution of a concentration of 50% or more.

Claim 3

A maleimide resin composition according to claim 1, further comprising a curing accelerator selected from the group of organic amines, imidazoles or onium salts.

Claim 4

A maleimide resin composition according to claim 1, wherein said adduct has a molecular weight from about 450 to about 4300.

Claim 5

A process for producing a heat resistant resin, comprising heating and reacting a reaction mixture comprising (I) a maleimide compound of the general formula: ##STR14## wherein A represents a mono-, di-, tri- or tetravalent organic group containing at least two carbon atoms and n represents an integer of 1-5 and (II) an ether bond-containing diamine compound of the general formula: ##STR15## wherein R 1 through R 4 which are the same or different from one another represent a hydrogen atom, a lower alkyl group, a lower alkoxyl group, chlorine atom or bromine atom, and R 5 and R 6 which are the same as or different from each other represent hydrogen atom, methyl group, ethyl group, trifluoromethyl group or trichloromethyl group.

Claim 6

A process for producing a heat resistant resin, comprising heating and reacting a reaction mixture comprising (I) a maleimide compound of the general formula: ##STR14## wherein A represents a mono-, di-, tri- or tetravalent organic group containing at least two carbon atoms and n represents an integer of 1-5 and (II) an ether bond-containing diamine compound of the general formula: ##STR15## wherein R 1 through R 4 which are the same or different from one another represent a hydrogen atom, a lower alkyl group, a lower alkoxyl group, chlorine atom or bromine atom, and R 5 and R 6 which are the same as or different from each other represent hydrogen atom, methyl group, ethyl group, trifluoromethyl group or trichloromethyl group.

Claim 7

A process for producing a heat resistant resin according to claim 4 wherein molar ratio of maleimide compound to diamine compound to be reacted is in the range of 10:1 to 1:1.2.

Claim 8

A process for producing a heat-resistant resin according to claim 4 wherein the reaction mixture comprises at least one curing accelerator selected from the group consisting of amines, imidazoles and onium salts.

Claim 9

A process for producing a maleimide resin which comprises the steps of reacting a maleimide compound having the general formula ##STR16## with a diamine having the general formula: ##STR17## to produce a maleimide-diamine adduct having the general formula: ##STR18## wherein A represents a mono-, di-, tri- or tetravalent organic group containing at least two carbon atoms, n represents an integer of 1 to 5, m represents an integer of 0 to 4, R 1 through R 4 which are the same or different represent hydrogen atom, a lower alkyl group, a lower alkoxy group, chlorine atom or bromine atom, and R 5 and R 6 which are the same or different represent hydrogen atom, methyl group, ethyl group, trifluoromethyl group or trichloromethyl group.

Claim 10

A process for producing a maleimide resin which comprises the steps of reacting a maleimide compound having the general formula ##STR16## with a diamine having the general formula: ##STR17## to produce a maleimide-diamine adduct having the general formula: ##STR18## wherein A represents a mono-, di-, tri- or tetravalent organic group containing at least two carbon atoms, n represents an integer of 1 to 5, m represents an integer of 0 to 4, R 1 through R 4 which are the same or different represent hydrogen atom, a lower alkyl group, a lower alkoxy group, chlorine atom or bromine atom, and R 5 and R 6 which are the same or different represent hydrogen atom, methyl group, ethyl group, trifluoromethyl group or trichloromethyl group.

Claim 11

The heat resistant resin produced by the process of claim 4, 5 or 6.

Claim 12

A maleimide resin composition comprising a maleimide-diamine adduct produced by heating and reacting a reaction mixture comprising at least one maleimide compound selected from the group consisting of N,N'-hexamethylene bismaleimide, N-phenylmaleimide, N,N'-m-phenylene bismaleimide, N,N'-p-phenylene bismaleimide, N,N'-4,4'-diphenylmethane bismaleimide, N,N'-4,4'-diphenyl ether bismaleimide, N,N'-methylene bis(3-chloro-p-phenylene) bismaleimide, N,N'-4,4'-diphenylsulfone bismaleimide, N,N'-4,4'-dicyclo-hexylmethane bismaleimide, N,N'-α,α'-4,4'-dimethylenecyclohexane bismaleimide, N,N'-m-xylene bismaleimide, N,N'-4,4'-diphenylcyclohexane bismaleimide and polyvalent maleimides of the following formula obtained from aniline, formaldehyde condensate and maleic anhydride: ##STR19## with at least one ether bond-containing diamine compound selected from the group consisting of 2,2'-bis[4-(4-aminophenoxy)phenyl]propane, 2,2'-bis[3-methyl-4-(4-aminophenoxy)phenyl]propane, 2,2'-bis[3-chloro-4-(4-aminophenoxy)phenyl]propane, 2,2'-bis[3-bromo-4-(4-aminophenoxy)phenyl]propane, 2,2-bis[3-ethyl-4-(4-aminophenoxy)phenyl]propane, 2,2-bis[3-propyl-4-(4-aminophenoxy)phenyl]propane, 2,2-bis[3-isopropyl-4-(4-aminophenoxy)phenyl]propane, 2,2-bis[3-butyl-4-(4-aminophenoxy)phenyl]propane, 2,2-bis[3-sec.-butyl-4-(4-aminophenoxy)phenyl]propane, 2-2-bis[3-methoxy-4-(4aminophenoxy)phenyl]propane, 1,1-bis[4-(4-aminophenoxy)phenyl]ethane, 1,1-bis[3-methyl-4-(4-aminophenoxy)phenyl]ethane, 1,1-bis[3-chloro-4-(4-aminophenoxy)phenyl]ethane, 1,1-bis[3-bromo-4-(4-aminophenoxy)phenyl]ethane, bis[4-(4-aminophenoxy)phenyl]methane, bis[3-methyl-4-(4-aminophenoxy)phenyl]methane, bis[3-chloro-4-(4-aminophenoxy)phenyl] methane, bis[3-bromo-4-(4-aminophenoxy)phenyl]methane, 1,1,1,3,3-hexafluoro-2, 2-bis[4-(4-aminophenoxy)phenyl]propane, 1,1,1,3,3,3-hexachloro-2, 2-bis[4-(4-aminophenoxy)phenyl]propane, 3,3-bis[4-(4-aminophenoxy)phenyl]pentane, 1,1-bis[4-(4-aminophenoxy)phenyl]propane, 1,1,1,3,3,3-hexafluoro-2,2-bis[3,5-dimethyl-4-(4-aminophenoxy)phenyl]propane, 1,1,1,3,3,3-hexafluoro-2,2-bis-[3,5-dibromo-4-(4-aminophenoxy)phenyl]propane, and 1,1,1,3,3,3-hexafluoro-2,2-bis[3-methyl-4-(4-aminophenoxy)phenyl]propane.

Claim 13

A maleimide resin composition comprising a maleimide-diamine adduct produced by heating and reacting a reaction mixture comprising at least one maleimide compound selected from the group consisting of N,N'-hexamethylene bismaleimide, N-phenylmaleimide, N,N'-m-phenylene bismaleimide, N,N'-p-phenylene bismaleimide, N,N'-4,4'-diphenylmethane bismaleimide, N,N'-4,4'-diphenyl ether bismaleimide, N,N'-methylene bis(3-chloro-p-phenylene) bismaleimide, N,N'-4,4'-diphenylsulfone bismaleimide, N,N'-4,4'-dicyclo-hexylmethane bismaleimide, N,N'-α,α'-4,4'-dimethylenecyclohexane bismaleimide, N,N'-m-xylene bismaleimide, N,N'-4,4'-diphenylcyclohexane bismaleimide and polyvalent maleimides of the following formula obtained from aniline, formaldehyde condensate and maleic anhydride: ##STR19## with at least one ether bond-containing diamine compound selected from the group consisting of 2,2'-bis[4-(4-aminophenoxy)phenyl]propane, 2,2'-bis[3-methyl-4-(4-aminophenoxy)phenyl]propane, 2,2'-bis[3-chloro-4-(4-aminophenoxy)phenyl]propane, 2,2'-bis[3-bromo-4-(4-aminophenoxy)phenyl]propane, 2,2-bis[3-ethyl-4-(4-aminophenoxy)phenyl]propane, 2,2-bis[3-propyl-4-(4-aminophenoxy)phenyl]propane, 2,2-bis[3-isopropyl-4-(4-aminophenoxy)phenyl]propane, 2,2-bis[3-butyl-4-(4-aminophenoxy)phenyl]propane, 2,2-bis[3-sec.-butyl-4-(4-aminophenoxy)phenyl]propane, 2-2-bis[3-methoxy-4-(4aminophenoxy)phenyl]propane, 1,1-bis[4-(4-aminophenoxy)phenyl]ethane, 1,1-bis[3-methyl-4-(4-aminophenoxy)phenyl]ethane, 1,1-bis[3-chloro-4-(4-aminophenoxy)phenyl]ethane, 1,1-bis[3-bromo-4-(4-aminophenoxy)phenyl]ethane, bis[4-(4-aminophenoxy)phenyl]methane, bis[3-methyl-4-(4-aminophenoxy)phenyl]methane, bis[3-chloro-4-(4-aminophenoxy)phenyl] methane, bis[3-bromo-4-(4-aminophenoxy)phenyl]methane, 1,1,1,3,3-hexafluoro-2, 2-bis[4-(4-aminophenoxy)phenyl]propane, 1,1,1,3,3,3-hexachloro-2, 2-bis[4-(4-aminophenoxy)phenyl]propane, 3,3-bis[4-(4-aminophenoxy)phenyl]pentane, 1,1-bis[4-(4-aminophenoxy)phenyl]propane, 1,1,1,3,3,3-hexafluoro-2,2-bis[3,5-dimethyl-4-(4-aminophenoxy)phenyl]propane, 1,1,1,3,3,3-hexafluoro-2,2-bis-[3,5-dibromo-4-(4-aminophenoxy)phenyl]propane, and 1,1,1,3,3,3-hexafluoro-2,2-bis[3-methyl-4-(4-aminophenoxy)phenyl]propane.

Claim 14

A maleimide resin composition according to claim 9, produced from a mixture consisting essentially of said at least one maleimide and said at least one ether bond-containing diamine.

Claim 15

A maleimide resin composition according to claim 9, wherein said adduct has a molecular weight from about 450 to about 4300.

Claim 16

A maleimide resin composition according to claim 9, wherein said at least one maleimide compound is N,N'-4,4'-diphenylmethane bismaleimide and said at least one ether bond-containing diamine compound is 2,2-bis[4-(4-aminophenoxy)phenyl]propane.

Claim 17

A maleimide resin composition according to claim 9, wherein said at least one maleimide compound is N,N'-m-phenylene bismaleimide and said at least one ether bond-containing diamine compound is 2,2-bis[3-methyl-4-(4-aminophenoxy)phenyl]propane.

Claim 18

A maleimide resin composition according to claim 9, wherein said at least one maleimide compound is: ##STR20## and said at least one ether bond-containing diamine compound is 2,2-bis[4-(4-aminophenoxy)phenyl]propane.

Claim 19

A maleimide resin composition according to claim 9, wherein said at least one maleimide compound is N,N'-4,4-diphenylmethane bismaleimide and ##STR21## and said at least one ether bond-containing diamine compound is 2,2-bis[3-ethyl-4-(4-aminophenoxy)phenyl]propane.

Claim 20

A maleimide resin composition according to claim 9, wherein said reaction mixture contains a low boiling solvent selected from the group consisting of acetone, methyl ethyl ketone and methyl cellosolve.