Polyelectrolyte complex antibacterial agent in antibacterial material

• US 5,578,598 A
• Filed: 10/03/1994
• Issued: 11/26/1996
• Est. Priority Date: 11/29/1990
• Status: Expired due to Term

• Current Assignee: Mitsubishi Chemical Medience Corporation (Mitsubishi Chemical Group Corp.)
• Original Assignee: Iatron Laboratories, Inc.
• Inventors: Abe, Koji, Inaba, Satoshi, Tanaka, Mitsunao, Akimoto, Masaharu
• Primary Examiner(s): Wityshyn, Michael G.
• Assistant Examiner(s): Witz, Jean C.
• Application Number:
  US08/317,288
• Time in Patent Office: 785 Days
• Field of Search: 514/255, 514/642, 514/643, 514/561
• US Class Current: 514/2.4
• CPC Class Codes: A01N 2300/00 Combinations or mixtures of active ingredients covered by classes A01N27/00 - A01N65/48 with other active or formulation relevant ingredients, e.g. specific carrier materials or surfactants, covered by classes A01N25/00 - A01N65/48
• CPC Class Codes: A01N 33/12 Quaternary ammonium compounds
• CPC Class Codes: A01N 43/40 six-membered rings
• CPC Class Codes: A01N 43/60 1,4-Diazines; Hydrogenated 1,4-diazines
• CPC Class Codes: A01N 61/00 Biocides, pest repellants or attractants, or plant growth regulators containing substances of unknown or undetermined composition, e.g. substances characterised only by the mode of action
• CPC Class Codes: C08G 73/0226 Quaternisation of polyalkylene(poly)amines
• CPC Class Codes: C08G 73/026 Wholly aromatic polyamines
• CPC Class Codes: C08G 73/0273 Polyamines containing heterocyclic moieties in the main chain
• CPC Class Codes: C08G 73/028 Polyamidoamines
• CPC Class Codes: C08J 3/246 Intercrosslinking of at least two polymers
• CPC Class Codes: C08L 101/02 characterised by the presence of specified groups , e.g. terminal or pendant functional groups
• CPC Class Codes: C08L 2203/02 for biomedical use
• CPC Class Codes: C08L 2666/02 Organic macromolecular compounds, natural resins, waxes or and bituminous materials
• CPC Class Codes: C08L 5/00 Compositions of polysaccharides or of their derivatives not provided for in groups C08L1/00 or C08L3/00
• CPC Class Codes: C08L 5/08 Chitin; Chondroitin sulfate; Hyaluronic acid; Derivatives thereof
• CPC Class Codes: Y10T 428/31725 Of polyamide

Abstract

An antibacterial agent characterized by containing a polyelectrolyte complex prepared by reacting a cationic polymer containing N⁺ atoms in repeating units thereof and an anionic polymer containing --COO^--, --SO₃^--, or --PO₃^-- groups in repeating units thereof, and an antibacterial material carrying the above polyelectrolyte complex on a carrier.

Claims

1. Antibacterial agent comprising a polyelectrolyte complex prepared by reacting (a1) an aqueous solution of a cationic polymer of formula (I):

##STR43## wherein (i) R₁ and R₄ are, independently, an alkylene group of 1 to 10 carbon atoms, a group of the general formula ##STR44## wherein R₁₁ and R₁₂ are, independently, an alkylene group of 1 or 2 carbon atoms, or an arylene group, and R₂, R₃, R₅ and R₆ are, independently, an alkyl group of 1 to 3 carbon atoms, or (ii) R₁ forms, together with the 2 nitrogen atoms and R₂, R₃, R₅ and R₆ in the formula a group of the formula ##STR45## wherein R₂, R₃, R₅ and R₆ are, independently, an alkyl group of 1 to 3 carbon atoms, R₄ has the same meaning as above (i) , X₁ --is a halogen atom, and m is an integer of 5 to 500, and (b1) an aqueous solution of an anionic polymer of formula (IV);

##STR46## wherein u is 1 or 2, R₈₁ is a hydrogen atom;

an alkyl group of 1 to 4 carbon atoms;

an alkyl group of 1 to 4 carbon atoms substituted by a hydroxyl or mercapto group or by an alkylthio group of 1 to 3 carbon atoms;

or an imidazolylmethyl or indolylmethyl group;

s is 20 to 100, q is an integer of 10 to 1000, wherein the concentration ratio of the cationic sites of the cationic polymer and the anionic sites of the anionic polymer are within the range of 0.25 to 4.0, and recovering a reaction product of (a1) and (b1) as a precipitate.

3. A method for imparting an antibacterial property to a material which comprises applying to said material the antibacterial agent of claim 1.

4. A synthetic or natural material having a coating of the antibacterial agent of claim 1.

5. An antibacterial agent according to claim 1, wherein the cationic polymer is the polymer of formula (I) wherein R₁ and R₄ are, independently, a straight or branched alkylene group of 2 to 8 carbon atoms, and R₁₁ and R₁₂ are bonded to the p-position, is used.

6. An antibacterial composition comprising an antibacterially effective amount of the antibacterial agent of claim 5 and a carrier.

7. An antibacterial agent according to claim 1, wherein the compound (b1) of the general formula (IV), wherein R₈₁ a hydrogen atom, or a methyl, isopropyl, isobutyl, s-butyl, hydroxymethyl, hydroxyethyl, methylthioethyl, mercaptomethyl, 5-imidazolylmethyl or 3-imidazolylmethyl group, is used.

2. An antibacterial agent comprising a polyelectrolyte complex of formula (IV):

##STR47## wherein (i) R₁ and R₄ are, independently, an alkylene group of 1 to 10 carbon atoms, a group of the general formula ##STR48## wherein R₁₁ and R₁₂ are, independently, an alkylene group of 1 or 2 carbon atoms, or an arylene group, and R₂, R₃, R₅ and R₆ are, independently, an alkyl group of 1 to 3 carbon atoms, or (ii) R₁ forms, together with the 2 nitrogen atoms and R₂, R₃, R₅, and R₆ in the formula, a group of the formula ##STR49## wherein R₁₃ and R₁₆ are, independently, a hydrogen atom or an alkyl group of 1 to 3 carbon atoms, R₄ has the same meaning as above (i), and m is an integer of 5 to 500, wherein u is 1 or 2, R₈₁, is a hydrogen atom;

an alkyl group of 1 to 4 carbon atoms;

an alkyl group of 1 to 4 carbon atoms substituted by a hydroxyl or mercapto group or by an alkylthio group of 1 to 3 carbon atoms;

or an imidazolylmethyl or indolylmethyl group;

s is 20 to 100 and q is an integer of 10 to 1000, provided that 0.25≦

2 m/q≦

4.0.

8. An antibacterial composition comprising an antibacterially effective amount of the antibacterial agent of claim 2 and a carrier.

9. An antibacterial composition comprising an antibacterially effective amount of the antibacterial agent of claim 2 and a carrier.