Hydrogen phosphonates and polymer compositions containing them as flame retardants
AssigneeMonsanto Company
InventorGail H. Birum
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Abstract
The present invention relates to cyclic phosphorus compounds including cyclic hydrogen phosphonates and processes for the preparation thereof. The present invention relates to an improved process for the preparation of cyclic hydrogenphosphonates, which comprises the reaction of phosphorochloridites with formic acid in accordance with the general reaction set forth below: ##STR1## where R is an alkylene or haloalkylene group of a 1,2-glycol having from two to six carbon atoms, or a 1,3-glycol having from three to eight carbon atoms, and Z is Cl or Br. Ketone and sulfenyl derivatives are also a part of the present invention. The cyclic phosphorus compounds are useful as flame retardants with organic polymers, such a polyurethanes, polyesters and polyamides.
Claims23
A cyclic phosphorus compound having the formula ##STR20## where Y is selected from the group consisting of ##STR21## and ##STR22## and where X is selected from the group consisting of
- --S(R.sub.c)
- where R.sub.c is phenyl with 0 to 5 halogens, or phenyl with 0 to 2 nitro groups, or methyl with 0 to 3 chlorine atoms, and ##STR23## where R.sub.d is an alkyl radical of 1 to 4 carbon atoms, or phenyl.
The compound ##STR28##
The compound ##STR29##
The compound ##STR30##
Process for the preparation of cyclic hydrogenphosphonate which comprises admixing at 10.degree. C to 100.degree. C, formic acid with a cyclic phosphorochloridite having the formula ##STR31## where R is an alkylene, or haloalkylene group of a 1,2-glycol having from 2 to 8 carbon atoms, or of a 1,3-glycol having from 3 to 8 carbon atoms, and Z is Cl or Br.
Process for the preparation of the compound ##STR32## which comprises admixing at 10.degree. to 100.degree. C, formic acid with -chloro-5,5-bis(bromomethyl)-1,3,2-dioxaphosphorinane, ##STR33##
Process for the preparation of the compound ##STR34## which comprises admixing at 10.degree. to 100.degree. C, formic acid with
- . 9-dichloro-2,4,8,10-textraoxa-3,9-diphosphaspiro[5.5]undecane.
Process for the preparation of cyclic phosphorus compounds which comprises admixing at 10.degree. to 100.degree. C, formic acid with a phosphorochloridite selected from the group consisting of 2-chloro-5,5-dimethyl-1,3,2-dioxaphosphorinane, and 2-chloro-5-ethyl-5-methyl-1,3,2-dioxaphosphorinane, and 2-bromo-5,5-bis-(chloromethyl)-1,3,2-dioxaphosphorinane, and 2-chloro-4-methyl-1,3,2-dioxaphosphorinane, and 2-chloro-5-phenyl-1,3,2-dioxaphosphorinane, and 2-chloro-5-(4-fluoro-3-bromophenyl)-1,3,2-dioxaphosphorinane, 2-chloro-5,5-bis(bromomethyl)-1,3,2-dioxaphosphorinane, 3,9-dichloro-2,4,8,10-tetraoxa-3,9-diphosphaspiro[5.5]undecane.
Process for the preparation of a cyclic phosphorus compound which comprises admixing at 10.degree. to 100.degree. C, formic acid with a cyclic phosphorochloridite having the formula ##STR35## where R is an alkylene, or haloalkylene group of a 1,2-glycol having from 2 to 8 carbon atoms, or of a 1,3-glycol having from 3 to 8 carbon atoms, and Z is Cl or Br, and thereafter treating the reaction mixture with a sulfenyl chloride, (R.sub.c) SCl, where R.sub.c is phenyl with 0 to 5 halogen atoms, or phenyl with 0 to 2 groups, or methyl with 0 to 3 chlorine atoms.
Process for the preparation of a cyclic phosphorus compound which comprises admixing at 10.degree. to 100.degree. C, formic acid with a cyclic phosphorochloridite having the formula ##STR36## where R is an alkylene, or haloalkylene group of a 1,2-glycol having from 2 to 8 carbon atoms, or of a 1,3-glycol having from 3 to 8 carbon atoms, and Z is Cl or Br, and thereafter treating the reaction mixture with a ketone, ##STR37## where R.sub.d is an alkyl radical of 1 to 4 carbon atoms, or phenyl.
Process for the preparation of a cyclic phosphorus compound which comprises admixing at 10.degree. to 100.degree. C, formic acid with a mixture of a cyclic phosphorochloridite having the formula ##STR38## where R is an alkylene, or haloalkylene group of a 1,2-glycol having from 2 to 8 carbon atoms, or of a 1,3-glycol having from 3 to 8 carbon atoms, and Z is Cl or Br, and a ketone, ##STR39## where R.sub.d is an alkyl radical of 1 to 4 carbon atoms or phenyl
Dependencies are inferred from the claim text.