Aminotriazine phosphonates in plastics

Synthetic resins or natural rubbers -- part of the class 520 ser – Synthetic resins – Processes of preparing a desired or intentional composition...

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523451, 524556, 524560, 524565, 524601, 524606, 544195, 525453, 525417, C08K 504

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055345735

DESCRIPTION:

BRIEF SUMMARY
FIELD OF THE INVENTION

This invention relates to substituted triazine compounds and to their use. In particular, it relates to sym-triazine (1,3,5-triazine) compounds containing at least one phosphonate, phosphonamidate or phosphonamide group which are generally useful as flame retardants in various organic materials, for example plastics materials such as plastics sheet or film, foamed polymers, moulded plastics articles or fibrous materials such as textiles. Many of the phosphorus-containing triazine compounds have spumescent properties, that is to say they foam at high temperatures and can be used in intumescent coatings or claddings which form an expanded char acting as protective insulation in a fire. Many of the phosphorus-containing triazine compounds are also useful as corrosion inhibitors, for example in surface coatings which inhibit corrosion of metals to which they are applied or which inhibit rust staining.


BACKGROUND OF THE INVENTION

U.S. Pat. No. 3,210,350 describes sym-triazine compounds having one or two of the three ring carbon atoms attached to a phosphonic radical of the formula: ##STR4## where R represents hydrogen or a saturated hydrocarbon group of up to 12 carbon atoms and X represents -OR or -NR.sub.2 ; the other ring carbon atom(s) are attached to a hydroxy, mercapto, nitro, acyl, acyloxy, amino, alkoxy, aryloxy, cycloalkyloxy, alkylsulpho, arylsulpho, cycloalkylsulpho, ureido, hydrazino, alkyl, aryl or cycloalkyl group. The compounds are stated to be useful as fire retardants, rust inhibitors, chemical intermediates, rust removers, electroplating additives, herbicides, insecticides, ion exchange resins, tanning agents, water-soluble interfacial agents, water-insoluble dispersion agents, detergents, wetting agents, gasoline inhibitors and monomers for vinyl polymerisation and copolymers. U.S. Pat. No. 3,158,450 describes the use of such a compound or a metal derivative thereof as an additive to leaded gasoline to inhibit engine misfiring. U.S. Pat. No. 3,011,998 describes condensation products of such triazine compounds with an aldehyde.
An article by J. P. Moreau and L. H. Chance in "American Dyestuff Reporter", May 1970 at pages 37-38 and 64-65 describes the evaluation of 2-amino-4,6-bis(diethoxyphosphinyl)-1,3,5-triazine and 2,4-diamino-6-diethoxyphosphinyl-1,3,5-triazine as possible flame retardant finishes for cotton. An article by the same authors in the same Journal in February 1971 at pages 34-38 describes the evaluation of the formaldehyde derivative of 2,4-diamino-6-diethoxyphosphinyl-1,3,5-triazine as a flame retardant for cotton. U.S. Pat. No. 3,654,274 describes new processes for preparing this compound.
An article by J A Mikroyannidis in J Polymer Science: Part A; Polymer Chemistry, Vol. 26, pages 583-593 (1988) describes linear poly(dialkoxyphosphinyl-sym-triazine)s prepared by interfacial or solution polycondensation reactions of various diamines such as ethylene diamine, hexamethylene diamine or bis(4-aminocyclohexyl) methane with 2-dialkoxyphosphinyl-4,6-dichloro-sym-triazines.


SUMMARY OF THE INVENTION

According to one aspect of the invention a plastics material contains a phosphorus-containing heterocyclic flame retardant and is characterised in that the flame retardant is a sym-triazine compound of the formula: ##STR5## or a polymer comprising repeating units of the formula: ##STR6## where R.sup.1 represents hydrogen, an alkyl or cycloalkyl group having 1 to 12 carbon atoms, an aryl or aralkyl group having 6 to 20 carbon atoms, a heterocyclic group having 2 to 14 carbon atoms and 1 to 4 hetero-atoms selected from N, S and O, or an -NH.sub.2, -CONH.sub.2 or-NHCONH.sub.2 group, and R.sup.2 represents hydrogen or an alkyl or cycloalkyl group having 1 to 12 carbon atoms, or R.sup.1 and R.sup.2 are joined together so that the group R.sup.1 R.sup.2 N- is a heterocyclic group having 2 to 14 carbon atoms and 0 to 3 hetero-atoms selected from N, S and O in addition to the N atom bonded to the triazine ring;
G.sup.1 and G.sup.2 are each independently selected from

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Moreau et al., "New Method for Preparing Alkyl (Amino-s-triazinyl) phosphonates", Journal of Chemical & Engineering Data, vol. 15, No. 4, Oct., 1970, pp. 581-583.
T. Masai et al, "Triazine Derivatives", Chemical Abstracts, 83 (1):857, Abstract No. 10165K (Jul. 7, 1975).
W. Hewertson et al, "1,3,5-Triazines. Part III. Arbozov Reactions of Chlorotriazines", J. Chem. Society, 1670-1675 (1962).
J. Mikroyannidis, "Synthesis, Physical, and Thermal Properties of Linear Poly(dialkoxyphosphinyl-s-Triazines)s", J. Polymer Science: Part A, Polymer Chemistry, 26:583-593 (1988).

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