Use of organic oxyimide salts as flame retardants, flame-retardant plastic compositions, method for the production thereof and moulded part, paint or coating

Patent metadata

Field	Value
Publication number	US-10450442-B2
Application number	US-201515511410-A
Country	US
Kind code	B2
Filing date	Sep 16, 2015
Priority date	Sep 18, 2014
Publication date	Oct 22, 2019
Grant date	Oct 22, 2019

Abstract

The invention relates to the use of organic oxyimide salts as flame retardants for plastics and to a corresponding flame retardant plastic composition. The invention also relates to a method for producing said type of plastic composition or a molded part produced therefrom, a molding compound, a molded part, paint or a coating.

First claim

The invention claimed is:

1. A method for imparting flame retardancy to a plastic material comprising incorporating an organic oxyimide salt having at least one structural element of formula I

wherein R 1 is selected from the group consisting of inorganic cations, organic cations, and combinations thereof, into the plastic material; wherein
R 1 is ionically bonded to the remainder of the structural element of formula I; and wherein
R 1′ , upon each occurrence, is the same or different and is a linear or branched alkyl radical, a linear or branched alkylene radical, an aromatic radical, a heteroaromatic radical or both radicals R 1′ are joined to form a ring, the ring being saturated or unsaturated, substituted or unsubstituted and/or at least one or both radicals R 1′ or the radicals R 1′ are joined to form a ring comprising at least one further structural element of formula I.

2. The method according to claim 1 , wherein the organic oxyimide salt
a) comprises a structural element of formula I and has a structure according to one of the formulae:

b) comprises a structural element of formula I and has a structure according to one of the subsequent formulae:

 wherein
n is 0, 1, 2, 3 or 4, and
R 2 is selected from the group consisting of optionally substituted alkylene-, cycloalkylene-, arylene-, heteroarylene- or bridging acyl-radicals; or
c) comprises three structural elements of formula I and has a structure according to the formula

3. The method according to claim 2 , wherein R 2 is selected from the group consisting of —(CH 2 ) n — with n=1 to 18, —CH(CH 3 )—, —C(CH 3 ) 2 —, —CH(CF 3 )—, —O—, —S—, —SO 2 —, —NHCO—, —CO—, and —OC(O)O— and groups

wherein
the cycloaliphatic or aromatic ring systems contained in the above groups are unsubstituted or substituted by one or more alkyl- and/or alkoxy groups,
Q upon each occurrence, is the same or different and is selected from the group consisting of a chemical bond, —(CH 2 ) n — with n=1 to 18, —CH(CH 3 )—, —C(CH 3 ) 2 —, —CH(CF 3 )—, —C(CF 3 ) 2 —, —O—, —S—, —SO 2 —, —NHCO—, —CO—, and —C(O)—O—, and
m is 0 or 1 to 3.

4. The method according to claim 1 , wherein the plastic material is selected from the group consisting of
a) polymers made of olefins or diolefins,
b) polystyrene, polymethylstyrene, polyvinylnaphthalene, styrene-butadiene (SB), styrene-butadiene-styrene (SBS), styrene-ethylene-butylene-styrene (SEBS), styrene-ethylene-propylene-styrene, styrene-isoprene, styrene-isoprene-styrene (SIS), styrene-butadiene-acrylonitrile (ABS), styrene-acrylonitrile-acrylate (ASA), styrene-ethylene, styrene-maleic anhydride polymers and graft copolymers made of methylmethacrylate, styrene-butadiene and ABS (MABS),
c) halogen-containing polymers,
d) polymers of unsaturated esters,
e) polymers made of unsaturated alcohols and derivatives thereof,
f) polyacetals,
g) polyphenylene oxides and blends with polystyrene or polyamides,
h) polymers of cyclic ethers,
i) polyurethanes made of hydroxy-terminated polyethers or polyesters and aromatic or aliphatic isocyanates,
j) polyamides,
k) polyimides, polyamideimides, polyetherimides, polyesterimides, poly(ether)ketones, polysulfones, polyethersulfones, polyarylsulfones, polyphenylenesulfides, polybenzimidazoles, or polyhydantoins,
l) polyesters made of aliphatic or aromatic dicarboxylic acids and diols or made of hydroxycarboxylic acids,
m) polycarbonates, polyestercarbonates and blends thereof,
n) cellulose derivatives,
o) elastomeric, thermoplastic, non-thermoplastic, and duroplastic materials, and
p) mixtures, combinations, or blends thereof.

5. The method according to claim 1 , which includes incorporating at least one further flame retardant selected from the group consisting of
a) inorganic flame retardants,
b) nitrogen-containing flame retardants,
c) radical formers,
d) phosphorus-containing flame retardants,
e) halogen-containing flame retardants based on chlorine and bromine, optionally in combination with Sb 2 O 3 and/or Sb 2 O 5 ,
f) borates,
g) sulfur-containing compounds,
h) antidrip agents,
i) silicon-containing compounds, and
j) combinations or mixtures thereof.

6. The method according to the claim 5 , wherein the radical formers are selected from the group consisting of
a) N-alkoxyamines according to the structural formula,

wherein
R 3 is hydrogen or an optionally substituted alkyl-, cycloalkyl-, aryl-, heteroaryl- or acyl-radical,
R 4 is an alkoxy-, aryloxy-, cycloalkoxy-, aralkoxy- or acyloxy-radical, and
Z is hydrogen or an optionally substituted alkyl-, cycloalkyl-, aryl-, heteroaryl- or acyl-radical, the two radicals Z also being able to form a closed ring which is substituted optionally by ester-, ether-, amine-, amide-, carboxy- or urethane-groups,
b) azo compounds according to the structural formula,

 wherein
R 5 is an alkyl-, cycloalkyl- or aryl-radical,
R 6 upon each occurrence, is the same or different and is a linear or branched alkyl-radical,
R 7 upon each occurrence, is the same or different and is hydrogen or a linear or branched alkyl-radical, and
R 8 upon each occurrence, is the same or different and is an alkyl-, alkoxy-, aryloxy-, cycloalkyloxy-, aralkoxy- or acyloxy-radical,
c) dicumyl compounds according to the structural formula

 wherein R 7 upon each occurrence, is the same or different and is hydrogen or a linear or branched alkyl-radical,
d) and/or a polycumyl compound according to the structural formula

wherein
R 7 upon each occurrence, is the same or different and is hydrogen or a linear or branched alkyl-radical, and 2<n<100.

7. The method according to claim 5 , wherein the organic oxyimide salt and the at least one further flame retardant are incorporated in a weight ratio of 99:1 to 1:99.

8. The method according to claim 1 , wherein the organic oxyimide salt is incorporated in combination with at least one phosphorus-containing compound.

9. The method according to claim 1 , wherein the organic oxyimide salt, relative to the plastic material is incorporated at 0.01 to 30% by weight.

10. A flame-retardant plastic material composition, comprising or consisting of:
a) 60 to 99.9 parts by weight of at least one plastic material,
b) 0.1 to 40 parts by weight of at least one organic oxyimide salt, comprising at least one structural element of the formula I,

 R 1 being selected from the gro

Assignees

• Fraunhofer Ges Forschung

Inventors

• Pfaendner Rudolf
• Mazurowski Markus

Classifications

• C08K5/5393

  Phosphonous compounds, e.g. R—P(OR')2 · CPC title

• C08L23/12

  Polypropene · CPC title

• C08K5/3415

  Five-membered rings · CPC title

• C08K5/56

  Organo-metallic compounds, i.e. organic compounds containing a metal-to-carbon bond · CPC title

• C09K21/10

  containing nitrogen · CPC title