Poly(hexamethylenebiguanide)hydrochloride Chemical Properties

storage temp. 

Inert atmosphere,Room Temperature

solubility 

Water

form 

Solid

color 

White to off-white

InChI

InChI=1S/C10H23N5/c1-9(11)14-7-5-3-4-6-8-15-10(12)13-2/h3-8H2,1-2H3,(H2,11,14)(H3,12,13,15)

InChIKey

SAGIGHPRUJPLKX-UHFFFAOYSA-N

SMILES

C(=N)(C)NCCCCCCNC(=N)NC

CAS DataBase Reference

32289-58-0(CAS DataBase Reference)

EPA Substance Registry System

Poly(iminoimidocarbonyliminoimidocarbonyliminohexamethylene) hydrochloride (32289-58-0)

Safety Information

Hazardous Substances Data

32289-58-0(Hazardous Substances Data)

Poly(hexamethylenebiguanide)hydrochloride Usage And Synthesis

Description

PHMB is best known for its broad-spectrum antimicrobial and antifungal activity. It is the standard of care for treatment of Acanthamoeba keratitis and an ingredient in multipurpose contact lens solutions, such as Renu (Bauch & Lomb, Rochester, NY). PHMB is a cationic disinfectant that is effective against Gram-negative and Gram-positive bacteria through its electrostatic interaction with negative sites on the lipopolysaccharide component of bacterial cell membranes. 

Application

Polyhexanide (polyhexamethylene biguanide, PHMB) is a polymer used as a disinfectant and antiseptic. In dermatological use, it is spelled polihexanide (INN) and sold under names such as Lavasept, Serasept, Prontosan and Omnicide. PHMB has been shown to be effective against Pseudomonas aeruginosa, Staphylococcus aureus (also the methicillin-resistant type, MRSA), Escherichia coli, Candida albicans (yeast), Aspergillus brasiliensis (mold), vancomycin-resistant enterococci, and Klebsiella pneumoniae (carbapenem-resistant enterobacteriaceae).

Safety

On the 20th of April 2018, the european commission decided to ban preservative uses of PHMB PT9 (Fibre, leather, rubber and polymerised materials preservatives). It’s still allowed for uses as disinfectants PT2 (Disinfectants and algaecides not intended for direct application to humans or animals). Furthermore, PHMB has been declared as a candidate for substitution by the ECHA.

Chemical Properties

Colorless to pale yellow solution

Chemical Properties

Poly(hexamethylenebiguanide) hydrochloride is also used as a surface disinfectant and is alleged to be suitable for skin disinfection. This compound has a slow effectand does not meet the practical requirementsfor prophylactic antiseptics in this respect. Although it is somewhat less effective than benzalkonium chloride, it is sometimes used instead of benzalkonium because it is less foamproducing under use conditions.

Uses

Broad spectrum antimicrobial polymer; binds and disrupts cytoplasmic membranes

Preparation

The preparation method of Poly(hexamethylenebiguanide)hydrochloride:By a certain proportion of 1; the own bisguanides of 6-and catalyst join in reaction vessel; under nitrogen protection, said mixture is heated to 80-200 DEGC and reacts, react 2-24 hour; reaction terminates; cooling blowing, obtains poly hexamethylene biguanide, poly hexamethylene biguanide aqueous acid is neutralized to pH value 5-9; and performing filtering so as to obtain a polyhexamethylene biguanidine salt.

Biological Activity

Polyhexamethylene biguanide (PHMB) is a cationic polymer with antimicrobial and antiviral properties. It has been commonly accepted that the antimicrobial activity is due to the ability of PHMB to perforate the bacterial phospholipid membrane leading ultimately to its death.

Properties and Applications

Polyhexamethylene biguanide hydrochloride (PHMB) is a new environment-friendly cationic water-soluble polymer. It is a water solution that can be used as a broad spectrum and high efficient disinfectant. It is low toxic, steady, non-flammable, non-explosive, and basically non-corrosive to stainless steel, copper, carbon steel, wood, and plastic. Because of its special bactericidal mechanisms, almost all kinds of bacteria shall be killed efficiently and will not develop resistance action.

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