# US 5,350,848 A · Triazinylphosphonic acids and their use in self-extinguishing polymeric compositions

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- Number: US 5,350,848 A
- Document ID: US5350848A
- Status: Granted
- Kind: A
- Application number: 07/990,519
- Filed: 1992-12-15
- Granted: 1994-09-27
- Earliest claimed: 1991-12-18
- Assignees: Ministero deli'Universita e della Ricerca Scientifica e Tecnologica
- Inventors: Roberto Cipolli; Cristina Rossi; Roberto Oriani; Enrico Masarati; Gilberto Nucida
- Web page: https://patentgrep.com/patent/US5350848A

## CPC

- C08K 5/5373: containing heterocyclic rings not representing cyclic esters of phosphonic acids
- C07F 9/6521: Six-membered rings
- C07F 9/65583: {each of the hetero rings containing nitrogen as ring hetero atom}
- C08K: Use of inorganic or non-macromolecular organic substances as compounding ingredients (paints, inks, varnishes, dyes, polishes, adhesives C09)
- C07F: ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM (metal-containing porphyrins C07D487/22)

## Abstract

Triazinylphosphonic acids of general formula (I): ##STR1## obtained by subsequent condensation reaction of a cyanuric halide with a osphite and with amines, and then by hydrolysis reaction of the intermediate thus obtained; The compounds of general formula (I) are used in particular as flame retardant additives.

## Claims

### Claim 1

A triazinylphosphonic acid of the formula (I): ##STR47## wherein at least one of the radicals R, R.sub.1, R.sub.2 and R.sub.3 is selected from the group consisting of --CH.sub.2 --C.sub.m H.sub.2m --O--R.sub.4, --CH.sub.2 --C.sub.p H.sub.2p -- and ##STR48## in which: m is a whole number between 1 and 7;
p is a whole number between 1 and 5;
R.sub.4 is selected from the group consisting of H; C.sub.1 -C.sub.8 alkyl; C.sub.2 -C.sub.6 alkenyl; --C.sub.q H.sub.2q --O--R.sub.6, where q is a whole number between 1 and 4 and R.sub.6 is H or C.sub.1 -C.sub.4 alkyl; C.sub.6 -C.sub.12 cycloalkyl and C.sub.1 -C.sub.8 -alkyl-C.sub.6 -C.sub.12 -cycloalkyl; provided that when R.sub.4 is H, m is a whole number between 2 and 7; and
the radicals R.sub.5, which can be the same or different, are selected from the group consisting of H; C.sub.1 -C.sub.8 alkyl; C.sub.2 -C.sub.6 alkenyl; C.sub.6 -C.sub.12 cycloalkyl; C.sub.1 -C.sub.8 -alkyl-C.sub.6 -C.sub.12 -cycloalkyl; and C.sub.1 -C.sub.4 hydroxyalkyl; or
one or more pairs of radicals selected from the group consisting of (a) R and R.sub.1, (b) R.sub.2 and R.sub.3, and (c) the radicals R.sub.5 may be joined to form a heterocyclic radical selected from the group consisting of aziridine, pyrrolidine, piperidine, morpholine, thiomorpholine and piperazine, each of which may be substituted with from 1 to 4 C.sub.1 -C.sub.2 alkyl groups, and
the remaining radicals R, R.sub.1, R.sub.2 and R.sub.3, which can be the same or different, are selected from the group consisting of H; C.sub.1 -C.sub.8 alkyl; C.sub.2 -C.sub.8 alkenyl; C.sub.6 -C.sub.16 cycloalkyl; and C.sub.1 -C.sub.8 -alkyl-C.sub.6 -C.sub.12 -cycloalkyl, each of which may be substituted with a hydroxyl or C.sub.1 -C.sub.4 hydroxyalkyl group.

### Claim 2 (depends on 1)

The triazinylphosphonic acid of claim 1, wherein R is selected from the group consisting of --CH.sub.2 --C.sub.m H.sub.2m --O--R.sub.4, --CH.sub.2 --C.sub.p H.sub.2p -- and ##STR49## in which: m is a whole number between 1 and 7;
p is a whole number between 1 and 5;
R.sub.4 is selected from the group consisting of H; C.sub.1 -C.sub.8 alkyl; C.sub.2 -C.sub.6 alkenyl; --C.sub.q H.sub.2q --O--R.sub.6, where q is a whole number between 1 and 4 and R.sub.6 is H or C.sub.1 -C.sub.4 alkyl; C.sub.6 -C.sub.12 cycloalkyl and C.sub.1 -C.sub.8 -alkyl-C.sub.6 -C.sub.12 -cycloalkyl; provided that when R.sub.4 is H, m is a whole number between 2 and 7; and
the radicals R.sub.5, which can be the same or different, are selected from the group consisting of H; C.sub.1 -C.sub.8 alkyl; C.sub.2 -C.sub.6 alkenyl; C.sub.6 -C.sub.12 cycloalkyl; C.sub.1 -C.sub.8 -alkyl-C.sub.6 -C.sub.12 -cycloalkyl; and C.sub.1 -C.sub.4 hydroxyalkyl;
R is selected from the group consisting of H; C.sub.1 -C.sub.8 alkyl; C.sub.2 -C.sub.8 alkenyl; C.sub.6 -C.sub.16 cycloalkyl; C.sub.1 -C.sub.8 -alkyl-C.sub.6 -C.sub.12 -cycloalkyl, each of which may be substituted with a hydroxyl or C.sub.1 -C.sub.4 hydroxyalkyl group; and the radicals listed above for R; and
R.sub.2 and R.sub.3 are joined to form a heterocyclic radical selected from the group consisting of aziridine, pyrrolidine, piperidine, morpholine, thiomorpholine and piperazine, each of which may be substituted with from 1 to 4 C.sub.1 -C.sub.2 alkyl groups.

### Claim 3

A triazinylphosphonic acid of the formula (I): ##STR50## wherein R is selected from the group consisting of at least one of the radicals R, R.sub.1, R.sub.2 and R.sub.3 is selected from the group consisting of --CH.sub.2 --C.sub.m H.sub.2m --O--R.sub.4, --CH.sub.2 --C.sub.p H.sub.2p -- and ##STR51## in which: m is a whole number between 1 and 7;
p is a whole number between 1 and 5;
R.sub.4 is selected from the group consisting of H; C.sub.1 -C.sub.8 alkyl; C.sub.2 -C.sub.6 alkenyl; --C.sub.q H.sub.2q --O--R.sub.6, where q is a whole number between 1 and 4 and R.sub.6 is H or C.sub.1 -C.sub.4 alkyl; C.sub.6 -C.sub.12 cycloalkyl and C.sub.1 -C.sub.8 -alkyl-C.sub.6 -C.sub.12 -cycloalkyl; provided that when R.sub.4 is H, m is a whole number between 2 and 7; and
the radicals R.sub.5, which can be the same or different, are selected from the group consisting of H; C.sub.1 -C.sub.8 alkyl; C.sub.2 -C.sub.6 alkenyl; C.sub.6 -C.sub.12 cycloalkyl; C.sub.1 -C.sub.8 -alkyl-C.sub.6 -C.sub.12 -cycloalkyl; and C.sub.1 -C.sub.4 hydroxyalkyl; and
R.sub.1, R.sub.2 and R.sub.3 are each H.

### Claim 4 (depends on 1)

The triazinylphosphonic acid of claim 1, wherein R, R.sub.1, R.sub.2 and R.sub.3 are said pairs of radicals (a) and (b), and each of said pairs is joined to form said heterocyclic radical.