Heptaphosphorus-derived compounds as flame retardants

Patent metadata

Field	Value
Publication number	US-10414985-B2
Application number	US-201515128775-A
Country	US
Kind code	B2
Filing date	Mar 24, 2015
Priority date	Mar 27, 2014
Publication date	Sep 17, 2019
Grant date	Sep 17, 2019

Abstract

The invention relates to flame retardant compositions comprising heptaphosphorus-derived compounds and to novel heptaphosphorus-derived compounds.
These heptaphosphorus-derived compounds are especially useful for the manufacture of flame retardant compositions based on thermoplastic polymers, especially polyolefin homo- and copolymers, polycondensates, such as polyamides, or polyesters and duroplastic polymers, such as the ones based on polyepoxides.

First claim

The invention claimed is:

1. A composition, which comprises
a) a heptaphosphorus-derived (P 7 ) compound selected from the group consisting of zinc heptaphosphorus halide, triazine heptaphosphide, tris-trialkylsilyl-heptaphosphide and trialkylheptaphosphine; and
b) a polymer substrate.

2. The composition according to claim 1 , which comprises a) the heptaphosphorus-derived (P 7 ) compound selected from the group consisting of zinc heptaphosphorus chloride, melamine heptaphosphide, tris-trimethylsilyl-heptaphosphide and trialkylheptaphosphine of the formula
P 7 (R x ) 3   (I),

wherein R x represents a group of the partial formula
—CR 1 R 2 R 3   (A),

wherein
a) one of R 1 , R 2 and R 3 represents hydrogen;
one of R 1 , R 2 and R 3 represents C 1 -C 4 -alkyl, phenyl or C 1 -C 4 -alkyl substituted with phenyl; and
one of R 1 , R 2 and R 3 represents the group of the partial formula
—CH═CR a R b   (B),

wherein
one of R a and R b represents (C 1 -C 4 alkyl) 3 silyl; and the other
one of R a and R b represents C 1 -C 4 -alkyl, phenyl or C 1 -C 4 -alkyl substituted with phenyl; or
b) one of R 1 , R 2 and R 3 represents hydrogen;
one of R 1 , R 2 and R 3 represents C 1 -C 4 -alkyl, phenyl or C 1 -C 4 -alkyl substituted with phenyl; and
one of R 1 , R 2 and R 3 represents the group of the partial formula
—CH—C(═O)—R a   (C),

wherein
R a represents C 1 -C 4 -alkyl, phenyl or C 1 -C 4 -alkyl substituted with phenyl; or
wherein
c) one of R 1 , R 2 and R 3 represents hydroxy;
one of R 1 , R 2 and R 3 represents hydrogen; and
one of R 1 , R 2 and R 3 represents C 1 -C 4 -alkyl, phenyl or C 1 -C 4 -alkyl substituted with phenyl; or
d) one of R 1 , R 2 and R 3 represents hydroxy; and
two of R 1 , R 2 and R 3 represent C 1 -C 4 -alkyl, phenyl or C 1 -C 4 -alkyl substituted with phenyl.

3. The composition according to claim 2 , which comprises a) the heptaphosphorus-derived (P) compound selected from the group consisting of zinc heptaphosphorus chloride, melamine heptaphosphide, tris-trimethylsilyl-heptaphosphide and trialkylheptaphosphine (I), wherein
R x represents the group (A), wherein
a) one of R 1 , R 2 and R 3 represents hydrogen;
one of R 1 , R 2 and R 3 represents C 1 -C 4 -alkyl, phenyl or C 1 -C 4 -alkyl substituted with phenyl; and
one of R 1 , R 2 and R 3 represents the group (B), wherein
one of R a and R b represents (C 1 -C 4 alkyl) 3 silyl; and the other
one of R a and R b represents C 1 -C 4 -alkyl, phenyl or C 1 -C 4 -alkyl substituted
with phenyl; or

b) one of R 1 , R 2 and R 3 represents hydrogen;
one of R 1 , R 2 and R 3 represents C 1 -C 4 -alkyl, phenyl or C 1 -C 4 -alkyl substituted with phenyl; and
one of R 1 , R 2 and R 3 represents the group (C), wherein
R a represents C 1 -C 4 -alkyl, phenyl or C 1 -C 4 -alkyl substituted with phenyl.

4. The composition according to claim 3 , which comprises a) the heptaphosphorus-derived (P 7 ) compound selected from the group consisting of zinc heptaphosphorus chloride, melamine heptaphosphide, tris-trimethylsilyl-heptaphosphide and trialkylheptaphosphine (I), wherein
R x represents the group (A), wherein
a) one of R 1 , R 2 and R 3 represents hydrogen;
one of R 1 , R 2 and R 3 represents phenyl; and
one of R 1 , R 2 and R 3 represents the group (B), wherein
one of R a and R b represents trimethylsilyl; and the other
one of R a and R b represents phenyl; or

b) one of R 1 , R 2 and R 3 represents hydrogen;
one of R 1 , R 2 and R 3 represents phenyl; and
one of R 1 , R 2 and R 3 represents the group (C), wherein
R a represents phenyl.

5. The composition according to claim 1 , which comprises
a) the heptaphosphorus-derived (P 7 ) compound selected from the group consisting of zinc heptaphosphorus halide, triazine heptaphosphide, tris-trialkylsilyl-heptaphosphide and trialkylheptaphosphine; and
b′) wherein the polymer substrate is a thermoplastic polymer substrate.

6. The composition according to claim 5 , which comprises
a) the heptaphosphorus-derived (P 7 ) compound selected from the group consisting of zinc heptaphosphorus halide, triazine heptaphosphide, tris-trialkylsilyl-heptaphosphide and trialkylheptaphosphine; and
b″) wherein the polymer substrate comprises a polyfunctional epoxide compound, and, optionally, a hardener compound.

7. The composition according to claim 1 , which further comprises flame retardants and additives selected from the group consisting of tetraalkylpiperidine additives, polymer stabilizers, fillers and reinforcing agents.

8. The composition according to claim 7 , which further comprises at least one additional flame retardant selected from the group consisting of phosphorus flame retardants, nitrogen generating flame retardants, organohalogen containing flame retardants and inorganic flame retardants.

9. The composition according to claim 8 , wherein the additional flame retardant is a nitrogen containing compound selected from the group consisting of melamine cyanurate, melamine phosphate, melamine poly-phosphate, ammonium polyphosphate, melamine ammonium phosphate, melamine ammonium polyphosphate, melamine ammonium pyrophosphate, a condensation product of melamine with phosphoric acid and other reaction products of melamine with phosphoric acid and mixtures thereof.

10. The composition according to claim 8 , wherein the additional flame retardant is a phosphorus containing flame retardant selected from the group consisting of tetra(2,6-dimethylphenyl)resorcinol diphosphate, salts of di-C 1 -C 4 alkylphosphinic acid, salts of hypophosphoric acid and 9,10-dihydro-9-oxa-10-phosphorylphenanthrene-10-oxide (DOPO) and its derivatives.

11. The composition according to claim 7 , which additionally comprises at least one tetraalkylpiperidine derivative selected from the group consisting of
1-Cyclohexyloxy-2,2,6,6-tetramethyl-4-octadecylaminopiperidine,
bis(1-Octyloxy-2,2,6,6-tetramethylpiperidin-4-yl) sebacate,
2,4-bis[(1-Cyclohexyloxy-2,2,6,6-tetramethylpmeridin-4-yl)butylamino]-6-(2-hydroxy-ethylamino-s-triazine,
bis(1-Cyclohexyloxy-2,2,6,6-tetramethylpiperidin-4-yl) adipate,
2,4-bis[(1-Cyclohexyloxy-2,2,6,6-tetramethylpiperidin-4-yl)butylamino]-6-chloro-s-triazine,
1-(2-Hydroxy-2-methylpropoxy)-4-hydroxy-2,2,6,6-tetramethylpiperidine,
1-(2-Hydroxy-2-methylpropoxy)-4-oxo-2,2,6,6-tetramethylpiperidine,
1-(2-Hydroxy-2-methylpropoxy)-4-octadecanoyloxy-2,2,6,6-tetramethylpiperidine,
bis(1-(2-Hydroxy-2-methylpropoxy)-2,2,6,6-tetramethylpiperidin-4-yl) sebacate,
bis(1-(2-Hydroxy-2-methylpropoxy)-2,2,6,6-tetramethylpiperidin-4-yl) adipate,
2,4-bis {N-[1-(2-Hydroxy-2-methylpropoxy)-2,2,6,6-tetramethylpiperidin-4-yl]-N-butylamino}-6-(2-hydroxyethylamino)-s-triazine,
the reaction product of 2,4-bis[(1-cyclohexyloxy-2,2,6,6-tetramethylpiperidin-4-yl)-butylamino]-6-chloro-s-triazine with N,N′-bis(3-aminopropyl)ethylenediamine),
2,4-bis[(1-Cyclohexyloxy-2,2,6,6-tetramethylpiperidin-4-yl)butylamino]-6-(2-hydroxy-ethylamino)-s-triazine,
the oligomeric compound which is the condensation product of 4,4′-hexamethylene-bis(amino-2,2,6,6-tetramethylpiperidine) and 2,4-dichloro-6-[(1-cyclohexyloxy-2,2,6,6-tetramethylpiperidin-4-yl)butylamino]-s-triazine end-capped with 2-chloro-4,6-bis(dibutylamino)-s-triazine,
the compound of the formula

and the compound of the formula

in which n is from 1 to 15.

12. A process for induci

Assignees

• Basf Se

Inventors

• Krämer Roland H
• Deglmann Peter
• König Alexander
• Von Benten Rebekka
• Eisenhardt Andrea
• Menon Sindhu
• Reuter Frank
• Grützmacher Hansjörg
• Tondreau Aaron

Classifications

• C08K5/5406

  containing elements other than oxygen or nitrogen · CPC title

• C08K5/34922

  Melamine; Derivatives thereof · CPC title

• C07F9/6568

  having phosphorus atoms as the only ring hetero atoms · CPC title

• C01B25/06

  Hydrogen phosphides · CPC title

• C08K3/32

  Phosphorus-containing compounds · CPC title