Publication Date: 2016-Jun-03
The IP.com Prior Art Database
Disclosed is a polymeric, ionic compound comprising at least 5 imidazolium groups, which compound is obtainable by simultaneously reacting glyoxal, formaldehyde, at least one C4-C8alkylene diamine, at least one protic acid, and a C8-C20alkylamine, especially by simultaneously reacting glyoxal, formaldehyde, hexylene diamine, acetic acid and dodecylamine. The present polymeric, ionic compound comprising at least 5 imidazolium groups shows advantageous antimicrobial properties (i.e. biocidal Polyimidazolium compound), and may be used in various formulations for application fields including plant protection, personal care, home care, industrial or institutional or hospital disinfection, material protection, or pharmaceuticals.
Page 01 of 107
The present invention relates to a new formulation with antimicrobial activity, to a new antimicrobial polymer, to the use of said formulation and said polymer as a biocide e.g. in formulations for cleaning, disinfection and/or descaling purposes, as well as to a cleaning agent or disinfection agent or descaling agent comprising said formulation.
WO 2012/127009 describes a number of imidazolium polymers with activity against Staphylococcus aureus and Pseudomonas aeruginosa. It has now been found that certain polymers of this class may be derivatized inter alia to obtain defined end groups, and that such modified polymers unexpectedly show an improved antimicrobial action.
It has now been found that a certain class of such linear imidazolium polymers shows a distinctly improved biocidal effect when derivatized to obtain alkyl end groups ("alkyl capping"), especially when certain molecular weight ranges are met.
The invention thus provides polymeric, ionic compound comprising at least 5 imidazolium groups, typically at least 8 imidazolium groups, which contains alkyl moieties as end groups, which compound shows a good antimicrobial activity. In the following, the compound of the invention will be referred to as a polymeric compound, polyimidazolium or imidazolium polymer, notwithstanding the fact that properties of valuable species of short chain length (i.e. compounds comprising 8, 7, 6 or even only 5 imidazolium moieties in total) may vary with chain length, which species thus could, alternatively, be described as oligomers.
The alkyl end groups are typically selected from the group consisting of C8-C20alkyl groups, which may be straight chain or branched, such as octyl, 2-ethylhexyl, nonyl, decyl, undecyl, dodecyl, tridecyl, tetradecyl, pentadecyl, hexadecyl, heptadecyl, octadecyl, eicosyl.
Present end-capped imidazolium polymer is advantageously prepared in analogy to methods described in WO 2012/127009, WO 2010/072571, and literature cited therein by reaction of glyoxal (i.e. ethane-1,2-dione), formaldehyde and alkylene diamine, where, in addition, a defined end group is introduced. This can be effected e.g. by reacting the product obtained in WO 2012/127009 with a suitable alkylating agent such as an alkyl halogenide. Generally, the polymer of the invention is obtainable by one of the methods (i) to (iii):
Method (i) comprises reacting glyoxal, formaldehyde, at least one C4-C8alkylene diamine, at least one protic acid, and a C8-C20alkylamine.
Page 02 of 107
Method (ii) comprises a first step of reacting glyoxal, formaldehyde, at least one C4- C8alkylene diamine and at least one protic acid, followed by a second step of reacting the product obtained in the first step with a suitable C8-C20alkyl compound such as a C8- C20alkyl halogenide.
Method (iii) comprises a first step of reacting glyoxal, formaldehyde, at least one C4- C8alkylene diamine, at least one protic acid and a C8-C20alkylamine,