Process for making electro-optically active polymers

Claim 1

The method for making optically active polymers composed of a carbon-carbon backbone chain having the general formula: ##STR32## wherein X, Ar, Z 1 , R, [linking moiety], and P have the meanings set forth below, which comprises reacting in homogeneous solution in an aprotic polar solvent a polymer having the general composition [terminal moiety]--[linking moiety]--P wherein (a) P represents a polymeric carbon-carbon backbone chain having the structure ##STR33## (3) units of (1) or (2), above, copolymerized with (i) alkyl acrylate wherein the alkyl moiety contains from about 1-5 carbons, (ii) alkyl methacrylate wherein the alkyl moiety contains from about 1-5 carbons, (iii) acryl amide, (iv) methacryl amide, and (v) styrene; (b) the linking moiety is (1) --(CH 2 ) m --, (2) --(CH 2 ) m --O-- (3) ##STR34## (4) --(CH 2 ) m --O--CH 2 -- or (5) ##STR35## wherein m is an integer of from about 1-20; and (c) the terminal moiety is ##STR36## wherein (1) Z 1 is H or OH, (2) R is (i) H, (ii) alkyl, straight chain, branched or cyclic, having 1-20 carbon atoms, (iii) --C n H 2n OH wherein n is an integer of from about 1-20, or (iv) an alkylene bridging group having 2 to 4 carbon atoms connecting the N atom to the o- position of the aromatic ring to which the N atom is attached, with a diazonium salt having the general formula X--Ar--N.sub.2.sup.+ A.sup.- wherein (a) X is (1) --NO 2 , (2) --CN, (3) --COOR 3 wherein R 3 is alkyl, straight chain, cyclic or branched having 1-20 carbon atoms, (4) --CH═C(CN) 2 , or (5) --C(CN)═C(CN) 2 ; (b) Ar is selected from the group consisting of ##STR37## wherein Z 2 is (i) --H, (ii) --OH, or (iii) alkyl, straight chain, branched or cyclic, having from about 1-20 carbon atoms, ##STR38## (c) A - is the conjugate base of an organic strong acid or superacid HA which is: (1) substituted sulfonic acid R 5 SO 3 H wherein R 5 is (i) --CH 3 , (ii) --CH 2 (CF 2 ) n F wherein n is an integer of from about 1-10, or (iii) --(CF 2 ) n F wherein n is an integer of from 1-10; (2) substituted benzenesulfonic acid ##STR39## wherein R 6 is (i) --CH 3 , (ii) --Cl, (iii) --Br, or (iv) --NO 2 ; followed by recovering the desired reaction product from the reaction mixture.

Claim 2

The method for making optically active polymers composed of a carbon-carbon backbone chain having the general formula: ##STR32## wherein X, Ar, Z 1 , R, [linking moiety], and P have the meanings set forth below, which comprises reacting in homogeneous solution in an aprotic polar solvent a polymer having the general composition [terminal moiety]--[linking moiety]--P wherein (a) P represents a polymeric carbon-carbon backbone chain having the structure ##STR33## (3) units of (1) or (2), above, copolymerized with (i) alkyl acrylate wherein the alkyl moiety contains from about 1-5 carbons, (ii) alkyl methacrylate wherein the alkyl moiety contains from about 1-5 carbons, (iii) acryl amide, (iv) methacryl amide, and (v) styrene; (b) the linking moiety is (1) --(CH 2 ) m --, (2) --(CH 2 ) m --O-- (3) ##STR34## (4) --(CH 2 ) m --O--CH 2 -- or (5) ##STR35## wherein m is an integer of from about 1-20; and (c) the terminal moiety is ##STR36## wherein (1) Z 1 is H or OH, (2) R is (i) H, (ii) alkyl, straight chain, branched or cyclic, having 1-20 carbon atoms, (iii) --C n H 2n OH wherein n is an integer of from about 1-20, or (iv) an alkylene bridging group having 2 to 4 carbon atoms connecting the N atom to the o- position of the aromatic ring to which the N atom is attached, with a diazonium salt having the general formula X--Ar--N.sub.2.sup.+ A.sup.- wherein (a) X is (1) --NO 2 , (2) --CN, (3) --COOR 3 wherein R 3 is alkyl, straight chain, cyclic or branched having 1-20 carbon atoms, (4) --CH═C(CN) 2 , or (5) --C(CN)═C(CN) 2 ; (b) Ar is selected from the group consisting of ##STR37## wherein Z 2 is (i) --H, (ii) --OH, or (iii) alkyl, straight chain, branched or cyclic, having from about 1-20 carbon atoms, ##STR38## (c) A - is the conjugate base of an organic strong acid or superacid HA which is: (1) substituted sulfonic acid R 5 SO 3 H wherein R 5 is (i) --CH 3 , (ii) --CH 2 (CF 2 ) n F wherein n is an integer of from about 1-10, or (iii) --(CF 2 ) n F wherein n is an integer of from 1-10; (2) substituted benzenesulfonic acid ##STR39## wherein R 6 is (i) --CH 3 , (ii) --Cl, (iii) --Br, or (iv) --NO 2 ; followed by recovering the desired reaction product from the reaction mixture.

Claim 5

The method of any one of claims 1 through 3, wherein Ar in the diazonium salt is ##STR40## wherein Z 2 has the aforestated meaning.

Claim 6

The method of any one of claims 1 through 3, wherein Ar in the diazonium salt reactant is ##STR41##

Claim 7

The method of any one of claims 1 through 3, wherein Ar in the diazonium salt reactant is ##STR42##