Patent GB-927173-A (GB)
Title: Aromatic substituted isocyanurates
Inventor: PARRY GEOFFREY GORDON
IPC: C08G18/02
Filed: 1958-11-03
Abstract: Resin lacquers comprise isocyanurates containing the grouping <FORM:0927173/IV(a)/1> wherein R1, R2 and R3 are aromatic radical each joined to the same isocyanurate ring through a carbon atom which is part of an aromatic ring, R1 being the same as R2 but different from R3 or R1, R2 and R3 are all different.  According to Example 6, a lacquer comprises an ethyl acetate solution of an isocyanurate obtained by copolymerizing 4:41-diisocyanato diphenyl methane and 2:4-diisocyanato-tert. butyl benzene in specified manner, there being isocyanato substituents in the product, cyclohexanone, a solution of unmodified urea-formaldehyde resin in xylene/butanol, methyl isobutyl ketone and a polyester obtained from hexane-triol, adipic acid and phthalic anhydride.  Other suitable isocyanurates and their preparation are described (see Group IV(b)).  The above-defined isocyanurates may also be used as curing agents for or as components of isocyanate modified polyester or polyether rubbers. Specifications 809,809 and 821,158 are referred to.ALSO:Isocyanurates containing the grouping <FORM:0927173/IV(a)/1> wherein R1, R2 and R3 are aromatic radicals each joined to the same isocyanurate ring through a carbon atom which is part of an aromatic ring, which radicals may bear isocyanato groups or other substituents and wherein R1 is the same as R2 but different from R3 or wherein R1, R2 and R3 are all different, are prepared by copolymerizing an aromatic isocyanate with one or two different aromatic isocyanates, in proportions which yield an isocyanurate, in the presence of a substituted pyridine catalyst defined in Specification 821,158.  The products are stated to be novel and those obtained in Examples 1-3 are claimed per se.  They may be monoisocyanurates or, when an aromatic di- or polyisocyanate is used, isocyanurates containing two or more iso-cyanurate rings united by the residue of an aromatic di- or polyisocyanate.  The reaction may be effected at 0 DEG -150 DEG C., if desired in the presence of a solvent and may be terminated by addition of an acyl halide or Friedel-Crafts catalyst.  An isocyanate reactant may be used in its dimeric form.  The products may be used as adhesives or as curing agents for rubbers and components of lacquers (see Group IV(a)).  Examples describe the preparation of isocyanurates from (1) p-nitrophenyl isocyanate (1 mole) and p-tolyl isocyanate (2 moles); (2) p-nitrophenyl isocyanate (2 moles) and p-anisyl isocyanate (1 mole); (3) o-nitrophenyl isocyanate (2 moles) and diphenyl methane-4:41-diisocyanate (1 mole); (4) p-chlorophenyl isocyanate and p-tolyl isocyanate, the product being a 1:1 complex of 1-tolyl-3:5-dichlorophenyl isocyanurate and tri-chlorophenyl isocyanurate; (5) p-chlorophenyl isocyanate and phenyl isocyanate yielding a 1:1-complex of tri-chlorophenyl isocyanate and 1-phenyl-3:5-di-chlorophenyl isocyanurate; (6) 4:41-di-isocyanato diphenyl methane and 2:4-diisocyanatotert-butyl benzene, the product containing unchanged isocyanato groups.  Numerous other suitable aromatic isocyanates are specified.  The Provisional Specification includes a further example (5) wherein p-chlorophenyl isocyanate and p-anisyl isocyanate are interacted yielding a 1:1 complex of di-chlorophenyl methoxy phenyl isocyanurate and tri-chlorophenyl isocyanurate.  Specification 809,809 also is referred to.