# US 5,344,931 A · Salts of triazinic compounds with phosphorus oxyacids, and use of said compounds in self-extinguishing polymeric compositions

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- Number: US 5,344,931 A
- Document ID: US5344931A
- Status: Granted
- Kind: A
- Application number: 07/956,994
- Filed: 1992-10-06
- Granted: 1994-09-06
- Earliest claimed: 1991-10-11
- Assignees: Ministero dell'Universita' e della Ricerca Scientifica e Technologica
- Inventors: Roberto Cipolli; Enrico Masarati; Roberto Oriani; Mario Pirozzi; Gilberto Nucida
- Web page: https://patentgrep.com/patent/US5344931A

## CPC

- C08K 5/5317: Phosphonic compounds, e.g. R—P(:O)(OR')2
- C07D 251/70: Other substituted melamines
- C07F 9/11: with hydroxyalkyl compounds without further substituents on alkyl
- C07F 9/3834: {Aromatic acids (P-C aromatic linkage)}
- C07F 9/386: {containing hydroxy substituents in the hydrocarbon radicals}
- C07F 9/3873: {containing nitrogen substituent, e.g. N.....H or N-hydrocarbon group which can be substituted by halogen or nitro(so), N.....O, N.....S, N.....C(=X)- (X =O, S), N.....N, N...C(=X)...N (X =O, S)}
- C07F 9/4841: {Aromatic acids or derivatives (P-C aromatic linkage)}
- C07F 9/65742: {non-condensed with carbocyclic rings or heterocyclic rings or ring systems}
- C08K 5/5205: {Salts of P-acids with N-bases}
- C08K: Use of inorganic or non-macromolecular organic substances as compounding ingredients (paints, inks, varnishes, dyes, polishes, adhesives C09)
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)
- 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

Salts of triazinic compounds with phosphorus oxyacids, having the general rmula (I): ##STR1## obtained by salifying oligomeric derivatives of 2,4,6-triamino-1,3,5-triazine with a phosphorus-containing acid. The compounds with general formula (I) find use in particular as flame-retardant additives.

## Claims

### Claim 1

Salts of triazinic compounds with phosphorus oxyacids, having the general formula (I): ##STR85## wherein: R is H or
--[--C.sub.p H.sub.2p --]--O--R.sub.4
in which p is an integer comprised within the range of from 2 to 8; and
R.sub.4 is H; (C.sub.1 -C.sub.8)-alkyl; (C.sub.2 -C.sub.8)-alkenyl; --[--C.sub.q H.sub.2q --]--O--R.sub.5,
in which q is an integer comprised within the range of from 1 to 4; and
R.sub.5 is H or (C.sub.1 -C.sub.4)-alkyl; (C.sub.6 -C.sub.12)-cycloalkyl or alkylcycloalkyl; R.sub.1 is (C.sub.1 -C.sub.4)-alkyl or R; or the moiety: ##STR86## is replaced by a heterocyclic radical bonded to the triazinic ring through the nitrogen atom; wherein said heterocyclic radical is selected from the group consisting of aziridine, pyrrolidine, piperidine, and piperazine radicals;
n is an integer comprised within the range of from 2 to 50;
m is a numeral smaller than, or equal to, n;
z is a divalent or polyvalent radical falling within the scope of one of following formulae: ##STR87## wherein the --R.sub.6 radicals, which may be the same, or different from each other, are hydrogen or (C.sub.1 -C.sub.4)-alkyl; ##STR88## wherein t is an integer comprised within the range of from 2 to 14; R.sub.7 is hydrogen, (C.sub.1 -C.sub.4)-alkyl, (C.sub.2 -C.sub.6)-alkenyl, (C.sub.1 -C.sub.4)-hydroxyalkyl; ##STR89## wherein s is an integer comprised within the range of from 2 to 5 and w is an integer comprised within the range of from 1 to 3; ##STR90## wherein: X is a direct --C--C--; O; S; S--S; SO; SO.sub.2 ; NH; NHSO.sub.2 ; NHCO; N=N; CH.sub.2 bond;
R.sub.8 is hydrogen; hydroxy; (C.sub.1 -C.sub.4)-alkyl; (C.sub.1 -C.sub.4)-alkoxy; ##STR91## wherein "A" can be a saturated or unsaturated cycle; ##STR92## wherein s has the above defined meaning; ##STR93## wherein; R.sub.9 is hydrogen or (C.sub.1 -C.sub.4)-alkyl;
r is an integer comprised within the range of from 1 to 5;
the indexes s, which are the same, or may be different from each other, have the above defined meaning; ##STR94## wherein: R.sub.9 has the above defined meaning;
v is an integer comprised within the range of from 2 to 4;
d is either 1 or 2;
R.sub.2 is H; OH; --O--(C.sub.1 -C.sub.8)-alkyl; --O--(C.sub.6 -C.sub.12)-aryl, possibly substituted with a (C.sub.1 -C.sub.8)-alkyl; (C.sub.7 -C.sub.16)-aralkyl; (C.sub.1 -C.sub.4)-alkyl possibly substituted with a carboxy group; (C.sub.6 -C.sub.12)-aryl;
R.sub.3 is H; OH; --O--(C.sub.1 -C.sub.8)-alkyl; --O--(C.sub.6 -C.sub.12)-aryl, (C.sub.1 -C.sub.4)-alkyl; (C.sub.6 -C.sub.12)-aryl;
R.sub.3 furthermore is: ##STR95## wherein: R.sub.10 is hydrogen or (C.sub.1 -C.sub.12)-alkyl;
Y is OH or R.sub.10 ; ##STR96## wherein: R.sub.10 has the same meaning as defined hereinabove and R.sub.11 radicals, which are the same, or may be different from each other, are hydrogen or (C.sub.1 -C.sub.4)-alkyl;
or the moiety: ##STR97## is replaced by a heterocyclic radical bonded to the carbon atom through the nitrogen atom wherein said heterocyclic radical is selected from the group consisting of azirdine, pyrrolidine, piperidine, or piperazine radicals; ##STR98## wherein: R.sub.12 is hydrogen or (C.sub.1 -C.sub.8)-alkyl; and
w has the same meaning as defined hereinabove; ##STR99## wherein: R.sub.13 is hydrogen or hydroxy; ##STR100## wherein: u has the same meaning as defined above;
or
R.sub.2 and R.sub.3, taken together, may constitute a cyclic structure having the formula: ##STR101##

### Claim 2 (depends on 1)

Salts of triazinic compounds with phosphorus oxyacids according to claim 1, in which said phosphorus acid is selected from: hypophosphorous acid; phosphorous acid; phosphoric acid; pyrophosphoric acid; tripolyphosphoric acid; ethane-1,1,2-triphosphonic acid; 2-hydroxyethane-1,1,2-triphosphonic acid; propane-1,2,3-triphosphonic acid; isopropylphosphoric acid; n-butylphosphoric acid; di-n-butylphosphoric acid; di-isopropylphosphoric acid; di-n-pentylphosphoric acid; isooctylphosphoric acid; hexylphosphoric acid; 2-ethylhexylphosphoric acid; methylphosphonic acid; ethylphosphonic acid; n-propylphosphonic acid; n-butylphosphonic acid; aminomethylphosphonic acid; phenylphosphoric acid; phenylphosphonic acid; phenylphosphinic acid; di-n-butylpyrophosphoric acid; di-(2-ethylhexyl)pyrophosphoric acid; octylphenylphosphoric acid; 2-methylbenzylphosphonic acid; 1-aminoethane-1,1-diphosphonic acid; 1-hydroxyethane-1,1-diphosphonic acid; 1-hydroxydodecane-1,1-diphosphonic acid; 1-(N-methylamino)-ethane-1,1-diphosphonic acid; N,N-dimethylaminoethane-1,1-diphosphonic acid; N-butyl-aminomethane-1,1-diphosphonic acid; phosphonoacetic acid; 2-phosphonopropionic acid; 3-phosphonopropionic acid; 2-phosphonobutyric acid; 4-phosphonobutyric acid; 2-hydroxy-5,5-dimethyl-2-oxo-1,3,2-dioxophosphorinane; 3,9-dihydroxy-2,4,8,10-tetraoxo-3,9-diphosphaspiro-[5,5]-undecane-3,9-diox ido; amino-tris(methylenephosphonic) acid; ethylenediaminotetra(methylene-phosphonic) acid; hexamethylenediaminotetra(methylene-phosphonic) acid; diethylenetriaminopenta(methylenephosphonic) acid; and so forth.