Thermoplastic polyamide particles

Patent metadata

Field	Value
Publication number	US-11401382-B2
Application number	US-201716095465-A
Country	US
Kind code	B2
Filing date	Apr 25, 2017
Priority date	Apr 26, 2016
Publication date	Aug 2, 2022
Grant date	Aug 2, 2022

Abstract

Thermoplastic polyamide particles comprising at least one polyamide and at least one polymeric ionic compound comprising imidazolium groups (imidazolium compound), the thermoplastic polyamide particles having an ellipsoidal or approximately ellipsoidal shape with the largest diameter of 1 to 100 mm, preferably 2 to 10 mm, more preferably 3 to 8 mm.

First claim

The invention claimed is:

1. Thermoplastic polyamide particles comprising a mixture of at least one polyamide and at least one polymeric ionic compound comprising imidazolium groups (imidazolium compound), the thermoplastic polyamide particles having an ellipsoidal shape with the largest diameter of 1 to 100 mm, further comprising at least one particulate inorganic filler having a density of at least 2.5 g/cm 3 , the thermoplastic polyamide particles having a density of at least 1.65 g/cm 3 , and wherein the amount of particulate inorganic fillers, based on the thermoplastic polyamide particles, is 50 to 80 wt %, wherein an ellipsoidal shape is characterized by the diameter of the ellipsoid at any, arbitrarily selected position of the ellipsoid deviating by not more than 20% from the corresponding diameter of an ideal ellipsoid, wherein the polymeric ionic compound contains at least one end group capable of forming a covalent bond with the polyamide and wherein from mixing and heating of polymeric imidazolium compound and polyamide, a covalent bond or linkage between polymeric imidazolium compound and polyamide main chain is formed.

2. The thermoplastic polyamide particles according to claim 1 , wherein the polymeric ionic compound comprising imidazolium groups (imidazolium compound) is obtained by reacting
a) at least one α-dicarbonyl compound,
b) at least one aldehyde,
c) at least one amino compound having at least two primary amino groups,
d) optionally an amino compound having only one primary amino group and
e) at least one protic acid,
and optionally subjecting the reaction product to an anion exchange,
wherein the components a) and b) the aldehyde carbonyl groups may also be present as hemiacetal or acetal and the ketone carbonyl groups may also be present as hemiketal or ketal.

3. The thermoplastic polyamide particles according to claim 2 , wherein the main chain of the at least one imidazolium compound apart from the nitrogen atoms of the imidazolium groups does not contain any quaternary nitrogen atoms that bear 4 residues that are different from hydrogen.

4. The thermoplastic polyamide particles according to claim 2 , wherein component c) is selected from
amines of the formula 1 H 2 N-A-NH 2   (1)

wherein
A is a divalent aliphatic, alicyclic, aliphatic-alicyclic, aromatic or araliphatic radical, where the aliphatic moieties in the aforementioned aliphatic, aliphatic-alicyclic or araliphatic radicals may be interrupted by one or more nonadjacent groups which are selected from —O—, —S— and —N(R b )—, where R b is selected from hydrogen, C 1 -C 20 -alkyl and a group CH 2 CH 2 —O y —R c , wherein y is 1, 2, 3, 4, 5 or 6 and R c is hydrogen or C 1 -C 4 -alkyl; where alicyclic or aromatic moieties in the aforementioned alicyclic, aliphatic-alicyclic, aromatic or araliphatic radicals may be substituted by 1, 2, 3 or 4 radicals selected from C 1 -C 20 -alkyl, C 1 -C 20 -alkoxy, a radical of the formula
—O— CH 2 CH 2 O] z —R d , where R d is hydrogen or C 1 -C 4 -alkyl and z is 1, 2, 3, 4, 5 or 6; carboxyl and carboxylate, and where the aliphatic moieties in the aforementioned aliphatic, aliphatic-alicyclic or araliphatic radicals may be substituted by 1, 2, 3 or 4 radicals selected from C 1 -C 20 -alkoxy, a radical of the formula —O— CH 2 CH 2 O] z —R d , where R d is hydrogen or C 1 -C 4 -alkyl and z is 1, 2, 3, 4, 5 or 6, carboxyl and carboxylate; with the proviso that the aromatic or araliphatic radicals preferably do not contain 1,4-bound phenylene rings;

amines of the formula 2

in which
Y is CR C , N, C 2 -C 6 -alkyl or C 3 -C 6 -cycloalkyl;
E 1 , E 2 and E 3 , independently of each other, are a single bond, C 1 -C 10 -alkylene, —NR D —C 2 -C 10 -alkylene or —O—C 1 -C 10 -alkylene, with the proviso that E 1 , E 2 and E 3 are not a single bond and are not —NR D —C 2 -C 10 -alkylene when Y is N;
R C is H, C 1 -C 4 -alkyl, C 2 -C 4 -hydroxyalkyl or C 1 -C 4 -alkoxy; and
R B and R D , independently of each other, are H, C 1 -C 4 -alkyl, C 2 -C 4 -hydroxyalkyl or C 1 -C 4 -alkoxy; and
mixtures thereof
and/or wherein component c) is selected from nitrogen-comprising polymers.

5. The thermoplastic polyamide particles according to claim 4 , wherein
the divalent aliphatic radicals A are selected from linear and branched C 1 -C 30 -alkylene which may be interrupted by one or more nonadjacent groups which are selected from —O—, —S— and —N(R b )—, where R b is selected from hydrogen, C 1 -C 20 -alkyl and a group CH 2 CH 2 —O y —R c , wherein y is 1, 2, 3, 4, 5 or 6 and R c is hydrogen or C 1 -C 4 -alkyl; and/or may be substituted by 1, 2, 3 or 4 radicals selected from C 1 -C 20 -alkoxy, a radical of the formula —O— CH 2 CH 2 O] z —R d , where R d is hydrogen or C 1 -C 4 -alkyl and z is 1, 2, 3, 4, 5 or 6, carboxyl and carboxylate;
the divalent alicyclic radicals A are selected from C 5 -C 8 -cycloalkylene which may carry 1, 2, 3 or 4 C 1 -C 4 -alkyl radicals;
the divalent aliphatic-alicyclic radicals A are selected from C 1 -C 4 -alkylene-C 5 -C 8 -cycloalkylene, C 5 -C 8 -cycloalkylene-C 1 -C 4 -alkylene-C 5 -C 8 -cycloalkylene and C 1 -C 4 -alkylene-C 5 -C 8 -cycloalkylene-C 1 -C 4 -alkylene, with the cycloalkylene radicals possibly carrying 1, 2, 3 or 4 C 1 -C 4 -alkyl radicals;
the divalent aromatic radicals A are selected from 1,2-phenylene, 1,3-phenylene, naphthylene and biphenylene, with the phenylene radicals possibly carrying 1, 2, 3 or 4 radicals selected from C 1 -C 20 -alkyl, C 1 -C 20 -alkoxy and a radical of the formula —O— CH 2 CH 2 O] z —R d , where R d is hydrogen or C 1 -C 4 -alkyl and z is 1, 2, 3, 4, 5 or 6; and
the divalent araliphatic radicals A are selected from phenylene-C 1 -C 4 -alkylene, phenylene-C 1 -C 4 -alkylene-phenylene and C 1 -C 4 -alkylene-phenylene-C 1 -C 4 -alkylene, with the phenylene radicals possibly carrying 1, 2, 3 or 4 radicals selected from C 1 -C 20 -alkyl, C 1 -C 20 -alkoxy and a radical of the formula —O— CH 2 CH 2 O] z —R d , where R d is hydrogen or C 1 -C 4 -alkyl and z is 1, 2, 3, 4, 5 or 6.

6. The thermoplastic polyamide particles according to claim 4 , wherein component c) is selected from
compounds of the formula H 2 N—(CH 2 ) m —NH 2 , wherein m is an integer of 3 to 20, where a CH 2 group may be substituted by a carboxyl or carboxylate group;
compounds of the formula NH 2 [B—X] k —B—NH 2 ; in which X is O, each B independently is C 2 -C 6 -alkylene; and k is an integer from 1 to 100;
bis(4-aminocyclohexyl)methane, bis(3-aminocyclohexyl)methane, isophoronediamine, 1,1-bis(aminomethyl)cyclohexane, 1,2-bis(aminomethyl)cyclohexane, 1,3-bis(aminomethyl)cyclohexane, 1,4-bis(aminomethyl)cyclohexane, 2-aminopropylcyclohexylamine, 3(4)-aminomethyl-1-methylcyclohexylamine;
3-aminomethyl-benzylamine;
amines of the formula 2, wherein Y is CR C , where R C is H or C 1 -C 4 -alkyl, and E 1 , E 2 and E 3 , independently of each other, are —O—C 1 -C 6 -alkylene; and
mixtures thereof, or wherein component c) is a mixture of amino compounds, comprising at least one amine with two primary amino groups and at least one amine with more than two, in particular three, primary amino groups.

7. The thermoplastic polyamide particles according to claim 1 , wherein the anions of the at least one protic acid e) and/or the anions of the imidazolium compound are selected from:
the group of chloride, bromide and iodide,
the group of carboxylates and polybasic carboxylic acids,
the group of sulfates, sulfites and sulfonates, and
the group of phosphates.

8. The thermoplastic polyamide particles according to claim 1 ,

Assignees

• Basf Se

Inventors

• Schoemer Martina
• Lindner Jean-Pierre Berkan
• Kniesel Simon
• Wiethan Juergen

Classifications

• C08K2003/3045

  Sulfates · CPC title

• C11D3/3719

  Polyamides or polyimides · CPC title

• C08K2003/3036

  of zinc · CPC title

• C08K2003/2227

  of aluminium · CPC title

• C08G73/0616 Primary

  with only two nitrogen atoms in the ring · CPC title