Antibacterial agent

Details Antibacterial agent Antibacterial agent

1992-10-21

1994-11-22

Nagumo, Mark

Drug, bio-affecting and body treating compositions

Solid synthetic organic polymer as designated organic active...

Polymer from ethylenic monomers only

424 7831, 424 7832, 424405, 424409, 526274, 526278, 568 8, 568 11, 514134, A61K 3180, A61K 3166

Patent

active

053667271

DESCRIPTION:

BRIEF SUMMARY
TECHNICAL FIELD

The present invention relates to antibacterial agents and, more particularly, to antibacterial agents comprising as active ingredients a phosphonium salt having vinyl groups and/or a phosphonium salt polymer in which the phosphonium salt, a monomer, is polymerized.


BACKGROUND ART

Recently, a variety of antibacterial agents have been used in the fields of industry, agriculture, food processing industry and the like.
Although the greater part of the synthesized antibacterial agents previously used have been highly toxic, research has progressed towards antibacterial agents with decreased toxicity, to develop polymer type immobilized antibacterial agents that are water-insoluble and have little toxicity. These immobilized antibacterial agents can confer antibacterial activity on the surface of various materials, and thus have been used in different fields including the textile industry where, for example antibacterial agents are immobilized on the surface of antibacterial and deodorant textiles.
It is reported that in the immobilized polymer type antibacterial agents, the antibacterial agents themselves are immobilized in pendant form to polymers such as polyvinyl, polyacrylate, polymethacrylate, polyester and polyamide. For example, alkyl pyridinium salts and alkyl dimethylbenzyl ammonium salts are immobilized by polyvinyl chains, biganides by polyacrylate chains and polymethacrylate chains, and alkyl pyridinium salts by polyester chains and polyamide chains.
Most of the immobilized antibacterial agents practically used or being researched are those of quaternary ammonium salts.
Further, certain type of phosphonium salt compound are known as biologically active substances which have a broad antibacterial spectrum against bacteria, fungi and algae such as various nitrogen-containing compounds (Japanese Patent Laid-Open Nos.57-204286, 63-60903, 1-93596, 2-240090, and 62-114903).
Although the quaternary ammonium salt type immobilized antibacterial agents have a broad antibacterial spectrum, they do not have sufficient antibacterial activity for short periods of exposure to affect microorganisms. Phosphonium salt compound type antibacterial agents also do not have sufficient antibacterial activity, and vinylbenzyl phosphonium salt compounds according to the present invention have not yet been disclosed.


DISCLOSURE OF THE INVENTION

Accordingly, an object of the present invention is to overcome the above mentioned problems and to provide antibacterial agents which have a broad antibacterial spectrum, and have sufficient antibacterial activity through a short period of exposure.
As a result of intensive research, the present inventors have now found that certain kinds of phosphonium salt compound type antibacterial agents having vinyl groups can solve the above mentioned problems.
That is, in a first aspect of the present invention, there is provided an antibacterial agent comprising as an active ingredient a vinylbenzyl phosphonium salt of the general formula (I), ##STR2## wherein R.sub.1, R.sub.2 and R.sub.3 each represent a hydrogen atom, a linear or branched alkyl group having 1 to 18 carbon atoms, an aryl group, a hydroxyl group, or an alkoxyl-substituted alkyl, aryl or aralkyl group, and X.sup.- is an anion; and/or a phosphonium salt polymer in which the vinylbenzyl phosphonium salt, a monomer, is polymerized.
In a second aspect of the present invention, there is provided the above mentioned antibacterial agent in which a phosphonium salt polymer is a homopolymer of phosphonium salt of the general formula (II), ##STR3## wherein R.sub.1, R.sub.2 and R.sub.3 each represent a hydrogen atom, a linear or branched alkyl group having 1 to 18 carbon atoms, an aryl group, a hydroxyl group, or an alkoxyl-substituted alkyl, aryl or aralkyl group; X.sup.- is an anion; and n is an integer of 2 or more.
In a third aspect of the present invention, there is provided the above mentioned antibacterial agent in which the phosphonium salt polymer is a copolymer, whose degree of polymerization is 2 or more,

REFERENCES:
patent: 3065272 (1962-11-01), Garner et al.
patent: 3539684 (1970-11-01), Hoover
patent: 4749642 (1988-06-01), Kurematsu et al.
patent: 4855211 (1989-08-01), Janssens et al.

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