Back to results
US 7,645,877 B2Granted
Heptazine derivatives containing phosphorus, method for the production thereof and use thereof as flame retardants
AssigneesZylum Beteiligungsgesellschaft mbH & Co., Patente II KG
InventorsTobias Gmeiner, Edwin Kroke, Marcus Schwarz
Life of this patent
Estimating the term…
Abstract
The present invention relates to unsymmetrical and symmetrical phosphorus-comprising heptazine derivatives, represented by the formula (1): in which Ra, Rb and Rc are, independently of one another, an azide group —N3 or an —N═PR1R2R3 group, with the proviso that at least one radical from Ra, Rb and Rc is an —N═PR1R2R3 group, to a process for the preparation thereof and to the use thereof.
Claims10
A compound represented by the formula (1):
- in which Ra, Rb and Rc are, independently of one another, an azide group —N3 or an —N═PR1R2R3 group, with the proviso that at least one radical from Ra, Rb and Rc is an —N═PR1R2R3 group, and in which R1, R2 and R3 are, independently of one another, a radical chosen from the group α consisting of a straight-chain or branched-chain C1-C12-alkyl radical, a C3-C7-cycloalkyl radical, a straight-chain or branched-chain C2-C12-alkenyl radical, a straight-chain or branched-chain C1-C12-alkoxy radical, furyl, furanyl, benzofuranyl, thienyl, thiazolyl, benzothiazolyl, thiadiazolyl, imidazolyl, pyrazolyl, triazolyl, tetrazolyl, pyrazinyl, benzothienyl, morpholinyl, thiomorpholinyl, piperidinyl, piperazinyl, pyrrolidinyl, pyrimidinyl, imidazolinyl, pyrazolidinyl, phenyl, phenoxy, benzyl, benzyloxy, naphthyl, naphthoxy, di(C1-C6)alkylamino, tri(C1-C6)alkylsilyl and pyridyl, which can in each case be further substituted by one to five substituents chosen, independently of one another, from the group β consisting of a straight-chain or branched-chain C1-C6-alkyl radical, a C3-C7-cycloalkyl radical, a straight-chain or branched-chain C2-C6-alkenyl radical, a straight-chain or branched-chain C1-C6-alkoxy radical, halogen, hydroxy, amino, di(C1-C6)alkylamino, nitro, cyano, benzyl, 4-methoxybenzyl, 4-nitrobenzyl, phenyl and 4-methoxyphenyl.
A process for the preparation of a compound according to the formula (2), which comprises:
- reacting melem with phosphorus pentachloride in phosphorus oxychioride to produce C6N7(N═PCl3)3 as an intermediate;
- and
- reacting the intermediate with either compounds of the X—OH type or an organic metallic compound X—MgHal or Li—X to produce the compound according to formula (2), wherein X represents a radical chosen from the group α consisting of a straight-chain or branched-chain C1-C12-alkyl radical, a C3-C7-cycloalkyl radical, furyl, furanyl, benzofuranyl, thienyl, thiazolyl, benzothiazolyl, thiadiazolyl, imidazolyl, pyrazolyl, triazolyl, tetrazolyl, pyrazinyl, benzothienyl, morpholinyl, thiomorpholinyl, piperidinyl, piperazinyl, pyrrolidinyl, pyrimidinyl, imidazolinyl, pyrazolidinyl, phenyl, phenoxy, benzyl, benzyloxy, naphthyl, naphthoxy, di(C1-C6)alkylamino, tri(C1-C6)alkylsilyl and pyridyl, which can in each case be further substituted by one to five substituents chosen, independently of one another, from the group β consisting of a straight-chain or branched-chain C1-C6-alkyl radical, a C3-C7-cycloalkyl radical, a straight-chain or branched-chain C2-C6-alkenyl radical, a straight-chain or branched-chain C1-C6-alkoxy radical, halogen, hydroxy, ammo, di(C1-C6)alkylamino, nitro, cyano, benzyl, 4-methoxybenzyl, 4-nitrobenzyl, phenyl and 4-methoxyphenyl.
Dependencies are inferred from the claim text.