Polymer from nitrile terminated compounds having Schiff bonds and process for preparing the same

Claim 2

A polymer obtained by polymerizing a nitrile-terminated Schiff compound monomer by heating said monomer to a temperature sufficient to cause polymerization but below the temperature at which an exothermic reaction occurs, said monomer represented by the formula: X--(Z--Y--C.tbd.N).sub.n wherein n is a number of 1 or 2; Z represents --CH═N-- or --N═CH--; when n is 1, X represents a member of the group consisting of a C 1 -C 8 alkyl group, a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, or a C 3 -C 6 cycloalkyl group; Y represents a member of the group consisting of a straight or branched alkylene group having 2 to 12 carbon atoms, a substituted or unsubstituted phenylene group, a substituted or unsubstituted naphthylene group, a substituted or unsubstituted biphenylene group, a substituted or unsubstituted anthracene group, a substituted or unsubstituted phenathrene group, a substituted or unsubstituted pyrene group, or a divalent organic group represented by the formula ##STR37## wherein Q represents O, S, SO 2 , --(CH 2 )m--, CO, --(CF 2 ) m --, ##STR38## m represents a number of 1 to 12, and R 1 and R 2 are the same or different from one another and represent a member of the group consisting of H, CH 3 , C 2 H 5 , CF 3 , ##STR39## and when n is 2, X represents one of the divalent organic groups specified above wherein X and Y are the same or different from one another and a first Y the same or different from a second Y.

Claim 3

The polymer of claim 1 wherein said polymer has a cross-ladder skeleton structure.

Claim 4

The polymer of claim 1 further including a substituent selected from the group consisting of F, Cl, Br, CH 3 , CF 3 , OH, NH 2 , ##STR40##

Claim 5

The polymer of claim 1 wherein n represents 2 and X represents a member of the group consisting of ##STR41## and --(CH 2 ) m' --, wherein m' represents a number of 1 to 8, and Q represents a member of the group consisting of O, CO, S, SO 2 and ##STR42## with R 1 and R 2 being the same or different from each other and representing a member of the group consisting of H, CH 3 , C 2 H 5 , CF 3 , ##STR43##

Claim 6

The polymer of claim 1 wherein n represents 1 and X represents a member selected from the group consisting of a C 1 -C 8 alkyl group, ##STR44## wherein R 3 is a member of the group consisting of H, F, Cl, Br, CH 3 , CF 3 , OH, NH 2 , ##STR45##

Claim 7

The polymer of claim 1 wherein said nitrile-terminated Schiff compound monomer is polymerized in the presence of an ethylenic polymerizable compound.

Claim 8

The polymer of claim 1 wherein said nitrile-terminated Schiff compound monomer is polymerized in the presence of an N, N'-substituted bismaleimide compound.

Claim 9

A polymer obtained by polymerizing a monomer of a nitrile-terminated Schiff compound represented by the formula X--(Z--Y--C.tbd.N).sub.2 wherein Z represents --CH═N-- or --N═CH--; Y represents a straight or branched alkylene group having 1 to 12 carbon atoms, a substituted or unsubstituted phenylene group, a substituted or unsubstituted naphthylene group, a substituted or unsubstituted biphenylene group, a substituted or unsubstituted anthracene group, a substituted or unsubstituted phenanthrene group, a substituted or unsubstituted pyrene group or a divalent organic group represented by the formula ##STR46## wherein Q represents O, S, SO 2 , --CH 2 ) m --, CO, --(CF 2 ) m --, ##STR47## m represents a number of 1 to 12, and R 1 and R 2 are the same or different from one another and represent a member selected from the group consisting of H, CH 3 , C 2 H 5 , CF 3 , ##STR48## and X represents one of the divalent organic groups specified above wherein X and Y are the same or different from one another and a first Y is the same or different from a second Y.

Claim 10

A polymer obtained by polymerizing a monomer of a nitrile-terminated Schiff compound represented by the formula X--(Z--Y--C.tbd.N).sub.2 wherein Z represents --CH═N-- or --N═CH--; Y represents a straight or branched alkylene group having 1 to 12 carbon atoms, a substituted or unsubstituted phenylene group, a substituted or unsubstituted naphthylene group, a substituted or unsubstituted biphenylene group, a substituted or unsubstituted anthracene group, a substituted or unsubstituted phenanthrene group, a substituted or unsubstituted pyrene group or a divalent organic group represented by the formula ##STR46## wherein Q represents O, S, SO 2 , --CH 2 ) m --, CO, --(CF 2 ) m --, ##STR47## m represents a number of 1 to 12, and R 1 and R 2 are the same or different from one another and represent a member selected from the group consisting of H, CH 3 , C 2 H 5 , CF 3 , ##STR48## and X represents one of the divalent organic groups specified above wherein X and Y are the same or different from one another and a first Y is the same or different from a second Y.

Claim 11

The polymer of claim 8 wherein said polymer has a cross-ladder skeleton structure.

Claim 12

The polymer of claim 8 wherein said polymer includes a substituent selected from the group consisting of F, Cl, Br, CH 3 , CF 3 , OH, NH 2 , ##STR49##

Claim 13

The polymer of claim 8 wherein X represents a member of the group consisting of ##STR50## wherein m' represents a number of 1 to 8, and Q represents a member of the group consisting of O, CO, S, SO 2 and ##STR51## with R 1 and R 2 being the same or different from each other and representing a member of the group consisting of H, CH 3 , C 2 H 5 , CF 3 , ##STR52##

Claim 14

A process for producing a polymer, the process comprising: providing a nitrile-terminated Schiff compound monomer represented by the formula X--(Z--Y--C.tbd.N).sub.2 wherein Z represents --CH═N-- or --N═CH--; Y represents a straight or branched alkylene group having 1 to 12 carbon atoms, a substituted or unsubstituted phenylene group, a substituted or unsubstituted naphthylene group, a substituted or unsubstituted biphenylene group, a substituted or unsubstituted anthracene group, a substituted phenanthrene group, a substituted or unsubstituted pyrene group or a divalent organic group consisting of ##STR53## wherein Q represents O, S, SO 2 , --(CH 2 ) m --, CO, --CF 2 ) m --, ##STR54## m represents a number of 1 to 12, and R 1 and R 2 are the same or different from one another and represent a member selected from the group consisting of H, CH 3 , C 2 H 5 , CF 3 , ##STR55## and X represents one of the divalent organic groups specified above wherein X and Y are the same or different from one another and a first Y is the same or different from a second Y; applying heat energy to the nitrile-terminated Schiff compound at a temperature sufficient to polymerize the same.

Claim 15

A process for producing a polymer, the process comprising: providing a nitrile-terminated Schiff compound monomer represented by the formula X--(Z--Y--C.tbd.N).sub.2 wherein Z represents --CH═N-- or --N═CH--; Y represents a straight or branched alkylene group having 1 to 12 carbon atoms, a substituted or unsubstituted phenylene group, a substituted or unsubstituted naphthylene group, a substituted or unsubstituted biphenylene group, a substituted or unsubstituted anthracene group, a substituted phenanthrene group, a substituted or unsubstituted pyrene group or a divalent organic group consisting of ##STR53## wherein Q represents O, S, SO 2 , --(CH 2 ) m --, CO, --CF 2 ) m --, ##STR54## m represents a number of 1 to 12, and R 1 and R 2 are the same or different from one another and represent a member selected from the group consisting of H, CH 3 , C 2 H 5 , CF 3 , ##STR55## and X represents one of the divalent organic groups specified above wherein X and Y are the same or different from one another and a first Y is the same or different from a second Y; applying heat energy to the nitrile-terminated Schiff compound at a temperature sufficient to polymerize the same.

Claim 16

The process of claim 12 wherein the step of applying heat energy is replaced by a step of applying light energy.

Claim 17

The process of claim 12 wherein the step of applying heat energy to the nitrile-terminated Schiff compound calls for heating the monomer up to a temperature of about 180° C.

Claim 18

The process of claim 14 wherein the monomer is heated to a temperature between about 120° C. and 180° C.

Claim 19

The process of claim 12 wherein the polymer that is obtained includes a dihydrotriazine ring formed within its structural unit.

Claim 20

The process of claim 12 wherein the polymer that is obtained includes a cross-ladder skeleton.

Claim 21

The process of claim 12 further comprising the step of adding a cross-linking agent to the nitrile-terminated Schiff compound monomer.

Claim 22

The process of claim 18 wherein the cross-linking agent is an ethylenic polymerizable compound.

Claim 23

The process of claim 12 further comprising the step of adding an N, N'-substituted bismaleimide compound to the nitrile-terminated Schiff compound monomer.

Claim 24

A process for producing a polymer, the process comprising: providing a nitrile terminated Schiff compound monomer represented by the formula X--(Z--Y--C.tbd.N).sub.n wherein n is a number of 1 or 2; Z represents a --CH═N-- or --N═CH--; when n is 1, X represents a member of the group consisting of a C 1 -C 8 alkyl group, a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, or a C 3 -C 6 cycloalkyl group; and Y represents a member of the group consisting of a straight or branched alkylene group having 2 to 12 carbon atoms, a substituted or unsubstituted phenylene group, a substituted or unsubstituted naphthylene group, a substituted or unsubstituted biphenylene group, a substituted or unsubstituted anthracene group, a substituted or unsubstituted phenathrene group, a substituted or unsubstituted pyrene group, or a divalent organic group represented by the formula ##STR56## wherein Q represents O, S, SO 2 , --(CH 2 ) m --, CO, --(CF 2 ) m --, ##STR57## m represents a number of 1 to 12, and R 1 and R 2 are the same or different from one another and represent a member of the group consisting of H, CH 3 , C 2 H 5 , CF 3 , ##STR58## and when n is 2, X represents one of the divalent organic groups specified above wherein X and Y are the same or different from one another and a first Y is the same or different from a second Y; giving heat energy to the monomer at a temperature between about 120° C. and 180° C. to polymerize the monomer.

Claim 25

A process for producing a polymer, the process comprising: providing a nitrile terminated Schiff compound monomer represented by the formula X--(Z--Y--C.tbd.N).sub.n wherein n is a number of 1 or 2; Z represents a --CH═N-- or --N═CH--; when n is 1, X represents a member of the group consisting of a C 1 -C 8 alkyl group, a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, or a C 3 -C 6 cycloalkyl group; and Y represents a member of the group consisting of a straight or branched alkylene group having 2 to 12 carbon atoms, a substituted or unsubstituted phenylene group, a substituted or unsubstituted naphthylene group, a substituted or unsubstituted biphenylene group, a substituted or unsubstituted anthracene group, a substituted or unsubstituted phenathrene group, a substituted or unsubstituted pyrene group, or a divalent organic group represented by the formula ##STR56## wherein Q represents O, S, SO 2 , --(CH 2 ) m --, CO, --(CF 2 ) m --, ##STR57## m represents a number of 1 to 12, and R 1 and R 2 are the same or different from one another and represent a member of the group consisting of H, CH 3 , C 2 H 5 , CF 3 , ##STR58## and when n is 2, X represents one of the divalent organic groups specified above wherein X and Y are the same or different from one another and a first Y is the same or different from a second Y; giving heat energy to the monomer at a temperature between about 120° C. and 180° C. to polymerize the monomer.

Claim 26

The process of claim 21 further including the step of adding a cross-linking agent to the Schiff compound monomer compound.