Novel aromatic imine polymers and process for the preparation thereof

An aromatic imine polymer comprising A. 100 to 20 mol%, based on its entire recurring units, of a recurring unit of the formula (I)

• [r--y.sub.1 --ar(Z).sub.p Y.sub.2 ] (I)
• wherein Z is --SO.sub.2 -- or --CO--;
• p is 0 or 1;
• and when p is 0, --Ar-- is directly bonded to --Y.sub.2 --;
• R is an organic group of 2 to 50 carbon atoms;
• Ar is a divalent aromatic group not containing a primary or secondary amino group, a hydroxyl group, or a group substantially reactive with said amino and hydroxyl groups and is expressed by the following formula (II) ##STR203## wherein Ar.sub.1 is an aromatic ring group containing 6 to 20 carbon atoms and having a valence of (q + 2) or (q + 3);
• Ar.sub.2 is an aromatic ring group containing 6 to 20 carbon atoms and having a valence of (r + 2) or (r + 3);
• W.sub.1 and W.sub.2 are identical or different electron-attracting groups selected from nitro, cyano, sulfonic acid ester, carboxamide, and carboxyl groups;
• q and r are identical or different and each represent 1, 2, 3, or 4;
• m and n are 0 or 1, and when m is 0, n is also 0;
• the symbol . . . represents the presence or absence of a bond;
• E and E' are identical or different non-aromatic bridging groups selected from the group consisting of ##STR204## and alkylene groups containing 1 to 6 carbon atoms, R.sub.3 and R.sub.4 being identical or different and representing a hydrogen atom or an alkyl group containing 1 to 3 carbon atoms;
• and R' is a member selected from the group consisting of ##STR205## or an alkylene group containing 2 to 15 carbon atoms, wherein E" is a non-aromatic bridging group selected from one of the members of the group defining E and E', and the groups R and R' may have an inert substituent;
• Y.sub.1 and (Z).sub.p Y.sub.2 are bonded respectively to the nuclear carbon atoms of the aromatic ring, and when p is 0, Ar has an electron-attracting group capable of causing the nuclear carbon atoms to which Y.sub.1 and Y.sub.2 are bonded to have a Hammet .sigma. constant of substantially at least +1, and when p is 1, Ar has an electron-attracting group capable of causing the nuclear carbon atom to which Y.sub.1 is bonded to have a Hammet .sigma. constant of substantially at least +1;
• said electron-attracting group being at least one member selected from the group consisting of nitro, cyano, sulfone, sulfonic acid ester, sulfonamide, sulfonic acid, carboxylic acid ester, carboxamide, ketone and aldehyde;
• and Y.sub.1 represents the group ##STR206## and Y.sub.2 represents the group ##STR207## or --O--, in which R.sub.1 and R.sub.2 are identical or different and represent a hydrogen atom or a monovalent or divalent aliphatic hydrocarbon residual group containing 1 to 3 carbon atoms, and when one or both R.sub.1 and R.sub.2 are divalent aliphatic hydrocarbon residual groups containing 1 to 3 carbon atoms, R.sub.1 and/or R.sub.2 can be bonded to R or bonded directly to each other;
• and when both R.sub.1 and R.sub.2 are a hydrogen atom or a monovalent aliphatic hydrocarbon group, R is a divalent organic group;
• when one of R.sub.1 and R.sub.2 is a divalent atom or monovalent hydrocarbon group, R is a trivalent organic group;
• when both of R.sub.1 and R.sub.2 are a divalent hydrocarbon group, R is a divalent or tetravalent organic group;
• and
• B. the remainder (0 to 80 mol%) of the recurring units being a unit expressed by the following formula
• [R"-Q.sub.1 D Q.sub.2 ] (IV)
• wherein R" is an organic group of 2 to 50 carbon atoms;
• the symbol . . . represents the presence or absence of a bond;
• D is an organic group containing 2 to 30 carbon atoms and having a valence of 2 to 4;
• and Q.sub.1 and Q.sub.2 are identical or different bridging groups selected from the group consisting of ##STR208## R.sub.5 and R.sub.6 being identical or different and representing a hydrogen atom or a monovalent or divalent hydrocarbon group having 1 to 3 carbon atoms.