Novel polyaromatic cyanates and polytriazines prepared therefrom

Claim 2

A polyaromatic cyanate which corresponds to the formula wherein: Ar is an aromatic radical; B . is a C 7-20 polycyclic aliphatic radical; D is independently in each occurrence any non- active hydrogen-containing substituent; q, r and s are independently in each occur- ence the integers 0, 1, 2, or 3; with the proviso that the sum of q, r and s is greater than or'equal to 2; t is independently in each occurrence an integer of between about 0 and 4 inclusive; and x is a number between about 0 and 5 inclusive.

Claim 3

The composition of Claim 1 wherein: Ar is a benzene, naphthalene, phenanthracene, anthracene, or biaromatic radicals, or two or more aromatic radicals bridged by alkyelne moieties; B is and D is an alkyl, alkenyl, alkynyl, aryl, alkaryl, aralkyl, halo, alkoxy, nitro, carboxy- . late, sulfone, sulfide, or carbonate moiety; D 1 is C 1-5 alkyl; Y is q, r and s are independently 1 or 2; t is independently 0, 1 or 2; and x is a number between about 0 and 2 inclusive.

Claim 4

The composition of Claim 2 wherein: Ar is a benzene, biphenyl, binaphthyl or diphenylalkylene radical; B is D is a C 1-10 alkyl, C 1-10 alkenyl, nitro or halo moiety; q, r and s are 1; t is 0 or 1; and x is a number between 0 and 1 inclusive.

Claim 5

The composition of Claim 3 wherein: Ar is benzene; B is D is a C 1-3 alkyl, C 1-3 alkenyl, bromo or chloro moiety; and t is 0.

Claim 6

The composition of Claim 4 wherein:

Claim 7

The composition of Claim 1 which corresponds to the formula wherein x is a real number of between about 0 and 5, inclusive-

Claim 8

The composition of Claim 6 wherein x is a real number of between about 0 and 2, inclusive.

Claim 9

The composition of Claim 6 wherein x is a real number of between about 0 and 1, inclusive.

Claim 10

A process for the preparation of an aromatic polycyanate which comprises (a) preparing in situ a cyanogen chloride by contacting a solution of chlorine in a chlorinated hydrocarbon with an aqueous solution of an alkali metal cyanide at a temperature of 0°C or below under conditions such that a cyanogen chloride is prepared; (b) physically separating the chlorinated hydrocarbon in which the cyanogen chloride is dissolved from the aqueous layer in which an alkali metal chloride salt is dissolved; and (c) contacting the cyanogen chloride dissolved in the chlorinated hydrocarbon with a polycyclic bridged hydroxy-substituted polyaromatic compound dissolved in a chlorinated hydrocarbon, a secondary alcohol or a tertiary alcohol, in the presence of a tertiary amine at a temperature of about 0°C or less under conditions such that a polyaromatic cyanate is prepared; wherein the.polycyclic bridged hydroxy-substituted polyaromatic compound corresponds to the formula wherein the polyaromatic cyanate corresponds to the formula wherein: Ar is an aromatic radical; B is a C 7-20 polycyclic aliphatic radical; D is independently in each occurrence any non- active hydrogen-containing substituent; q, r and s are independently in each occurrence the integers 0, 1, 2, or 3; with the proviso that the sum of q, r and s is greater than or equal to 2; t is independently in each occurrence an integer of between about 0 and 4 inclusive; and x is a number between about 0 and 5 inclusive.

Claim 11

A process for the preparation of an aromatic polycyanate which comprises (a) preparing in situ a cyanogen chloride by contacting a solution of chlorine in a chlorinated hydrocarbon with an aqueous solution of an alkali metal cyanide at a temperature of 0°C or below under conditions such that a cyanogen chloride is prepared; (b) physically separating the chlorinated hydrocarbon in which the cyanogen chloride is dissolved from the aqueous layer in which an alkali metal chloride salt is dissolved; and (c) contacting the cyanogen chloride dissolved in the chlorinated hydrocarbon with a polycyclic bridged hydroxy-substituted polyaromatic compound dissolved in a chlorinated hydrocarbon, a secondary alcohol or a tertiary alcohol, in the presence of a tertiary amine at a temperature of about 0°C or less under conditions such that a polyaromatic cyanate is prepared; wherein the.polycyclic bridged hydroxy-substituted polyaromatic compound corresponds to the formula wherein the polyaromatic cyanate corresponds to the formula wherein: Ar is an aromatic radical; B is a C 7-20 polycyclic aliphatic radical; D is independently in each occurrence any non- active hydrogen-containing substituent; q, r and s are independently in each occurrence the integers 0, 1, 2, or 3; with the proviso that the sum of q, r and s is greater than or equal to 2; t is independently in each occurrence an integer of between about 0 and 4 inclusive; and x is a number between about 0 and 5 inclusive.

Claim 12

10 A polytriazine which comprises the reaction product of (a) between about 1 and 100 mole percent of an aromatic polycyanate which corresponds to the formula ' wherein: Ar is an aromatic radical; B is a C 7-20 polycyclic aliphatic radical; D.is independently in each occurrence any nonactive hydrogen-containing substituent; q, r and s are independently in each occurrence the integers 0, 1, 2, or 3; with the proviso that-the sum of q, r and s is greater than or equal to 2; t is independently in each occurrence an integer of between about 0 and 4 inclusive; and x is a number between about 0 and 5 inclusive; . (b) between about 0 and 99 mole percent of one or more cyanate containing compounds, wherein x is a real number of between about 0 and 5, inclusive.

Claim 13

10 A polytriazine which comprises the reaction product of (a) between about 1 and 100 mole percent of an aromatic polycyanate which corresponds to the formula ' wherein: Ar is an aromatic radical; B is a C 7-20 polycyclic aliphatic radical; D.is independently in each occurrence any nonactive hydrogen-containing substituent; q, r and s are independently in each occurrence the integers 0, 1, 2, or 3; with the proviso that-the sum of q, r and s is greater than or equal to 2; t is independently in each occurrence an integer of between about 0 and 4 inclusive; and x is a number between about 0 and 5 inclusive; . (b) between about 0 and 99 mole percent of one or more cyanate containing compounds, wherein x is a real number of between about 0 and 5, inclusive.

Claim 14

The polytriazine of Claim 10 wherein the cyanate-containing compound corresponds to the formula ArfOCN) n wherein Ar is an aromatic radical and n is an integer of between 1 and 5, inclusive.

Claim 15

The polytriazine of Claim 10 wherein the cyanate-containing compound corresponds to the formula wherein each R is the same or different and represents hydrogen, halogen, straight and branched . C 1- C 20 alkyl, phenyl, alkoxy radicals having from 1 to 4 carbon atoms, alkoxy carbonyl radicals having from 1 to 4 carbon atoms in the alkyl group or; two adjacent radicals R on the same nucleus may together form a carbocyclic 5- or 6-membered ring, two adjacent radicals R may, together with a hetero atom (0, S, N), form a 5- or 6-membered heterocyclic ring, R' has the same meaning as R or represents the group A represents a direct bond, a C 1 -C 20 alkylene group optionally substituted by C 1 -C 4 alkyl or phenyl, a cycloaliphatic or aromatic 5- or 6-membered ring optionally interrupted by oxygen, a sulfonyl group (-SO 2 -), a carbonyl dioxide group, or a carbonyl group; a represents a number of from 1 to 5 when e≧1, and a number of from 2 to 5 when e=0; b represents 5-a when e≧1 and 6-(a+d) when e=0; c represents 5-d; d represents a number of from 0 to 5, and e represents 0, 1, 2 or 3, with a proviso that the sum of a and d is always a number from 2 to 5.