Compositions containing polymeric, ionic compounds comprising imidazolium groups

Patent metadata

Field	Value
Publication number	US-10016354-B2
Application number	US-201213427287-A
Country	US
Kind code	B2
Filing date	Mar 22, 2012
Priority date	Mar 23, 2011
Publication date	Jul 10, 2018
Grant date	Jul 10, 2018

Abstract

The present invention relates to compositions containing polymeric, ionic compounds comprising imidazolium groups. In particular, it relates to the use of polymeric, ionic compounds comprising imidazolium groups in personal care compositions and/or in biocide compositions.

First claim

The invention claimed is:

1. A biocide composition comprising an ionic polymer produced by a process comprising polymerizing
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, and
d) optionally an amino compound having only one primary amino group in the presence of
e) at least one protic acid,
to provide a polymer product;
and optionally subjecting the reaction product to an anion exchange,
the ionic polymer having a weight average molecular weight of from 2000 to 200,000, and has a dispersity PDI of 1.1 to 20,
where in 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;
where the main chain of the at least one compound comprising imidazolium groups does not contain 1,4-bound phenylene rings;
where the amino compound having at least two primary amino groups is not 1,3-diamino-2-hydroxy-propane or 1,3-diamino-2-hydroxy-2-methyl-propane; and
where the polymer comprises at least 10 repeat units each comprising an imidazolium ring;
and at least one carrier and/or at least one auxiliary agent.

2. The composition as claimed in claim 1 , 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.

3. The composition as claimed in claim 1 , wherein component a) comprises or consists of glyoxal or a hemiacetal or acetal thereof.

4. The composition as claimed in claim 1 , wherein component b) comprises or consists of a formaldehyde source or an aldehyde of formula R 3 —CHO, where R 3 is selected from C 1 -C 20 -alkyl, a group —CH 2 [O—CH 2 CH 2 ] x —OR a , wherein x is 1, 2, 3, 4, 5 or 6 and R a is hydrogen or C 1 -C 4 -alkyl; and phenyl which may be substituted by 1, 2, 3, 4 or 5 radicals selected from C 1 -C 20 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 20 -alkoxy, C 1 -C 6 -haloalkoxy and NR′R″, where R′ and R′R″ are, independently of each other, selected from hydrogen and C1-C6-alkyl; or comprises or consists of a formaldehyde source.

5. The composition as claimed in claim 1 , 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 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 —C2-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.

6. The composition as claimed in claim 5 , 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; or
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 1, 2, 3, 4, 5 or 6.

7. The composition as claimed in claim 5 , wherein component c) is selected from the group consisting of
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, 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.

8. The composition as claimed in claim 1 , 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 primary amino groups.

9. The composition as claimed in claim 1 , wherein component c) is a polyvinylamine polymer, polyalkylenimine, polyamidoamine or a mixtures thereof.

10. The composition as claimed in claim 1 , wherein the at least one protic acid e) is not a hydrohalic acid and the

Assignees

• Konradi Rupert
• Siemer Michael
• Sobotka Bettina
• Koltzenburg Sebastian
• Haberecht Monika
• Lindner Jean Pierre Berkan
• Rosenbaum Claudia
• Mueller Bernd
• Riggs Richard
• Lauterwasser Erica May Wilson
• Montag Jurith
• Basf Se

Inventors

• Konradi Rupert
• Siemer Michael
• Sobotka Bettina
• Koltzenburg Sebastian
• Haberecht Monika
• Lindner Jean-Pierre Berkan
• Rosenbaum Claudia
• Müller Bernd
• Riggs Richard
• Lauterwasser Erica May Wilson
• Montag Jurith

Classifications

• A61P17/10

  Anti-acne agents · CPC title

• A61P17/08

  Antiseborrheics · CPC title

• A61Q17/00

  Barrier preparations; Preparations brought into direct contact with the skin for affording protection against external influences, e.g. sunlight, X-rays or other harmful rays, corrosive materials, bacteria or insect stings · CPC title

• A61K31/787

  containing heterocyclic rings having nitrogen as a ring hetero atom · CPC title

• A61K8/84 Primary

  obtained by reactions otherwise than those involving only carbon-carbon unsaturated bonds · CPC title