Patent GB-905609-A (GB)
Title: Polymeric compounds containing s-triazine nuclei
Inventor: ADER GEORGE
IPC: C08G73/06
Filed: 1958-03-14
Abstract: Polcondensates having either the formula <FORM:0905609/IV(a)/1> or the formula <FORM:0905609/IV(a)/2> in which formulae, R is an alkyl or alkoxy group having 1 to 4 carbon atoms, a phenyl group, an amino group having one or more of these groups as substituents, or a halogen atom; R1 is alkyl of 1 to 4 carbon atoms, phenyl or hydrogen; R2 is phenylene or ethylene or is not present; and n is at least 2, may be prepared by self-condensation by heating of an amino-halo-s-triazine of formula <FORM:0905609/IV(a)/3> or by reacting, either in solution in presence of triethylamine or by direct anhydrous fusion, at least one halo-s-triazine of formula <FORM:0905609/IV(a)/4> with at least one compound R1NH-R2-NHR1.  The invention also includes the preparation of cross-linked polycondensates by reacting a polycondensate of formula <FORM:0905609/IV(a)/5> with at least one triazine having at least two replaceable halogen atoms when R is alkylamino or alkoxyamino of 1 to 4 carbon atoms; or with at least one polyfunctional compound containing amino, secondary amino or hydroxyl group when R is a halogen atom; or by reacting together at least one compound of formula <FORM:0905609/IV(a)/6> and at least one compound of formula <FORM:0905609/IV(a)/7> (8) Cyanuric chloride heated with p-phenylene diamine gives a cross-linked resin.  (9) Methyl dichloro-s-triazine was reacted with p-phenylene (Z is R or R4NH; and R4 is alkyl of 1 to 4 carbons, phenyl or hydrogen); or by reacting a cyanuric halide with R1NH-R2-NHR1.  In the examples, (1) 2-phenyl-4-anilino-6-chloro-s-triazine is self-condensed at 300 DEG C. with elimination of HCl; (2) 2,4-dianilino-6-chloro-s-triazine is similarly condensed.  The product is cross-linked with 2-anilino- 4,6-dichloro-s-triazine. similar product may be obtained by direct heating of the mixed monomeric materials.  (3) 2-methylamino-4-dimethylamino-6-chloro-s-triazine was auto-condensed. (4) The starting material was 2-methyl-4-anilino-6-chloro-s-triazine. Similarly polycondensates may be prepared by heating 2-methyl-4-methylamino-6-chloro-s-triazine; 2-diphenylamino-4-anilino-6-chloro-s-triazine; 2-phenyl-4-methylamino-6-chloro-s-triazine, or 2-chloro-4,6-bis-ethyl-amino-s-triazine.  (5) 2-anilino-4,6-dichloro-s-triazine was self-condensed and the product cross-linked with 2,4-dianilino-6-phenyl-s-triazine (6) 2-phenyl-4-amino-6-chloro-s-triazine heated in nitrogen at 220 DEG -300 DEG C. gave a polymer of formula <FORM:0905609/IV(a)/8> (7) 2-methoxy-4,6-dichloro-s-triazine is condensed with p-phenylenediamine in dioxane containing trialkylamine.  The product has the formula <FORM:0905609/IV(a)/9> diamine in acetone solution and in presence of triethylamine to yield a product of formula <FORM:0905609/IV(a)/100> (10) In a similar manner a product of formula <FORM:0905609/IV(a)/111> was produced.  (11) Refluxing 2-phenyl-4,6-dichloro-s-triazine with phenylhydrazine in acetone containing triethylamine gave a product of formula <FORM:0905609/IV(a)/122> Similar condensations were effected between phenyl dichloro-s-triazine and m- or p-phenylene diamine or N,N1-dimethyl-p-phenylene diamine; cyanuric chloride and ethylene diamine or phenyl hydrazine.ALSO:The invention comprises polycondensates having either the formula <FORM:0905609/IV (b)/1> or the formula <FORM:0905609/IV (b)/2> in which formulae, R is an alkyl or alkoxy group having 1 to 4 carbon atoms, a phenyl group, an amino group having one or more of these groups as substituents, or a halogen atom; R1 is alkyl of 1 to 4 carbon atoms, phenyl or hydrogen; R2 is phenylene or ethylene or is not present; and n is at least 2. The above polycondensates may be prepared by self-condensation by heating of an amino-halo-s-triazine of formula <FORM:0905609/IV (b)/3> in which X represents a halogen atom, or by reacting, either in solution in presence of triethylamine or by direct anhydrous fusion at least one halo-s-triazine of formula <FORM:0905609/IV (b)/4> in which X represents a halogen atom, with at least one compound R1NH-R2-NHR1.  In the examples, (1) 2-phenyl-4-anilino-6-chloro-s-triazine is self-condensed at 300 DEG C. with elimination of HCl.  (2) 2,4-dianilino-6-chloro-s-triazine is similarly condensed.  (3) 2-methylamino - 4-dimethylamine-6-chloro-s-triazine was auto-condensed.  (4) The starting material was 2-methyl-4-anilino-6-chloro-s-triazine. Similarly polycondensates may be prepared by heating 2-methyl-4-methylamino-6-chloro-s-triazine; 2 - diphenylamino-4-anilino-6-chloro-s-triazine; 2-phenyl-4-methylamino-6-chloro-s-triazine, or 2-chloro-4,6-bisethylamino-s-triazine.  (5) 2-anilino-4,6-dichloro-s-triazine was self-condensed.  (6) 2-phenyl-4-amino-6-chloro-s-triazine heated in nitrogen at 220-300 DEG C. gave a polymer of formula <FORM:0905609/IV (b)/5> (7) 2-methoxy-4,6-dichloro-s-triazine is condensed with p-phenylenediamine in dioxane containing triethylamine.  The product has the formula <FORM:0905609/IV (b)/6> (9) Methyl dichloro-s-triazine was reacted with p-phenylene diamine in acetone solution and in presence of triethylamine to yield a product of formula <FORM:0905609/IV (b)/7> (10) In a similar manner a product of formula <FORM:0905609/IV (b)/8> was produced.  (11) Refluxing 2-phenyl-4,6-dichloro-s-triazine with phenylhydrazine in acetone containing triethylamine gave a product of formula <FORM:0905609/IV (b)/9> Similar condensations were effected between phenyl dichloro-s-triazine and m of p-phenylene diamine or N,N1-dimethyl-p-phenylene diamine; cyanuric chloride and ethylene diamine or phenyl hydrazine.