CA1164338A - Disinfectant composition containing a quaternary ammonium and a polymer of hexamethylene beguanide hydrochloride - Google Patents

Disinfectant composition containing a quaternary ammonium and a polymer of hexamethylene beguanide hydrochloride

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Publication number
CA1164338A
CA1164338A CA000378586A CA378586A CA1164338A CA 1164338 A CA1164338 A CA 1164338A CA 000378586 A CA000378586 A CA 000378586A CA 378586 A CA378586 A CA 378586A CA 1164338 A CA1164338 A CA 1164338A
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Prior art keywords
composition
polymer
quaternary ammonium
phmb
hydrochloride
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Expired
Application number
CA000378586A
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French (fr)
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Nicolas Salkin
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    • CCHEMISTRY; METALLURGY
    • C11ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11DDETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D3/00Other compounding ingredients of detergent compositions covered in group C11D1/00
    • C11D3/48Medical, disinfecting agents, disinfecting, antibacterial, germicidal or antimicrobial compositions
    • AHUMAN NECESSITIES
    • A01AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01NPRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N47/00Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
    • A01N47/40Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having a double or triple bond to nitrogen, e.g. cyanates, cyanamides
    • A01N47/42Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having a double or triple bond to nitrogen, e.g. cyanates, cyanamides containing —N=CX2 groups, e.g. isothiourea
    • A01N47/44Guanidine; Derivatives thereof

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  • Life Sciences & Earth Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Engineering & Computer Science (AREA)
  • Health & Medical Sciences (AREA)
  • Agronomy & Crop Science (AREA)
  • Dentistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Pest Control & Pesticides (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Plant Pathology (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Organic Chemistry (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Abstract

ABSTRACT OF THE DISCLOSURE

The present invention relates to dininfectant compositions.
A bactericidal and fungicidal composition contains the polymer of hexamethylenehexamethylene biguanide (PHNB) and a quaternary ammonium compound. This composition brings an inoculum after one minute contact time to 0.0001% of the initial bacterial population, that is if the population count is 107 germs per ml, only 10 germs will survive. A film forming polymer can also be added, such as for example polyvinylpyrrolidone, in order to obtain a film showing long-lasting germicidal properties.
The invention finds an application in the disinfection of medical staff's hands and of linen and clothing soiled with proteins, blood, pus, etc.

Description

NEW DISINFECTANT COMPOS TION CONTAINING A QUATERNA~Y
~MMONIUM AND A POLYMER OF HEXAMETHYLENE BIGUANIDE HYDROCHLORIDE
. .
The present invention relates to a novel instantly and strongly ac-ting disinfectant composition.
Products with a residual bactericidal activity have been described previously by the inventor as possessing extended disinfectant properties for a certain length of time. The invention relates to a germicidal composition suitable for forming a film having a long lasting germ killing effect. The composition contains a solvent, one or more film-forming polymers soluble in the said solvent and one or more germicides. The film formed on the surface to which the product is applied has bactericidal properties due to the presence of germicides therein, which germicides are active against bacteria which could be deposited on the film coming from the atmosphere or through direct contact. One of the conditions previously mentioned is the perfect compatibility between the polymer or copolymer germicides and the solvent, and other possible additives. It is, however, essential that the germicides or their mixture if several are used show a maximum efficiency, that is speed of destruction and the widest possible spectrum of activity~
An aspect of this invention is as follows:
A novel bactericidal and fungicidal composition con-taining polymeric hexamethylene biguanide hydrochloride lPHMB) and a quaternary ammonium compound, the quaternary ammonium compound being didecyl dimethyl ammonium chloride IDDAC), the amount of PHMB being from 0.1 to 4~ and the amount of DDAC being from 0.01 to 1.5~.
An object of an aspect of the present invention is to widen the field of application previously described, by including applications on various surfaces such as walls, ceilings, door knobs, trolleys, operating tables, etc., and the aim is to extend the application of these compositions to human skint for example to disinfect surgeons' hands before they put on the surgical gloves, nurses' and others' hands. The purpose of these applications is to avoid . ,, ~
.'~;``''' J 1 6~1 33 la contamination of the medical staff by the patients and cross-infection between hospitalized patients. An object of an aspect of the invention is to ensure effective pre- and post-operative disinfection of the skin, of the operating theatre, of the drapes, to clean and disinfect : :j `3 ~ 6~33~

wounds and scars, etc. It was necessary to search for a powerful, yet non-irritating, non-diffusing, non~
penetrating through the skin, germicidal composition.
One product which has the required properties (in addition to the chlorhexidine salts previously des-cribed is the polymer (n = 4 - 7) of hexamethylene biguan-ide hydrochloride described in British Patents Nos.
702 268 and 1 ~67 249. This product has very low mammalian toxicity, LD 50 or rats is over 5000 mg/kg body weight.
At the concentrations recommended for use, no irritation of the skin or the eyes occurs. It is known to be non-allergic and it is free of systemic toxicity through the epidermis.
The replacement of chlorhexidine salts by poly-hexamethylene biguanide hydrochloride = PHMB shows manyadvantages. Chlorhexidine derivatives have very poor light stability, they are very unstable in the presence of most surfactants, cork, slight variation of pH, and in the presence of hypochlorites they form an indelible red dye and also there is always a danger of parachlor-aniline forming which is toxic.
Polyhexamethylene biguanide hydrochloride or PHMB is entirely free of the aforesaid disadvantages. Its germicidal activity is ~ery high and also very instan-taneous. A ~0~ aqueous solution of PHMB diluted to O.25%(i.e. 0.05~) destroys in 3 minutes, at 22C~ 99.99%
of a bacterial population, which means that an initial inoculum of 10 9 micro-organisms per ml is reduced to 0.01%, this representing still 10 5 bacteria per ml.
These tests were conducted with Staphilococcus Aureus, Escherichia Coli, Pseudomonas Aerugonosa and Saccharo-myces. The germicidal activity is hardly affected by the presence of proteins - 1 to 5~ of blood, 1% of milk, 1 of peptone. However, although very active against gram~
and gram- bacteria, PHMB has little activity against fungi (moulds). In order to compensate for this deficiency a small quantity of one or more qua-ternary ammonium com-pounds was added.
Surprisingly, it was discovered that the composition obtained by mixing PH~3 with a quaternary ammonium com-pound, had bactericidal and fun~icidal properties well above the individual activity of each component~ The created synergy is very important and the composition corresponding to this invention has a very strong and instantaneous activity against most micro-organisms.
After addition of the mixture of PHMB (0.15~) and didecyl dimethyl ammonium chloride (DDAC) at 0.03% to bacterial inoculum, the number of germs is reduced by 106 a~ter one minute of contact (99.9999~).
The same solution applied on the hands ~or one minute leaves 0 survivals on the surface of the skin, the normal bacterial population being 106. Such results cannot be obtained with any other products known today, keeping in mind the other properties required such as absence of irritation and toxicity.
This composition is particularly suitable when used with a film forming polymer since the deposi-ted film destroys instantly all the micro-organisms present on the surface and maintains its germicidal activity for a long time.
The quaternary ammonium compounds which can be used according to this invention are, for example :
alkvl dimethyl benzyl ammonium chloride, alkyl ethyl benzyl ammonium chloride, alkyl dimethyl 3,4-dichloro benzyl ammonium chloride, alkyl dimethyl benzyl ammonium saccharinate, octyl dodecyl dimethyl ammonium chloride, benzalkonium chloride, diisobutyl phenoxy ethoxy ethyl dimethy] benzyl ammonium chloride. However, the best results are obtained with didecyl dimethyl ammonium chloride which, in addition, has an excellent wetting I ~ 6~33~3 power~ lowering the ~surface tension of water to28 Dynes/cm.
The composition according to this invention contains 0.01~ to 1.5~ of DDAC and 0.1 to 4% of PHMB. It is a water and/or alcohol so]ution.
The following examples are given to illustrate non-restrictively how the composition according to the invention can be used.
COMPARATIVE EXAMPLE 1~: - Bactericidal activity of the polymeric (n=4-7) hexamethylene biguanide hydro-chloride -MHMB is used in solution in distilled water. An inoculum containing a given number of micro-oryanisms is added. After 3 mimltes of exposure, the surviving bac-teria are counted in powers of lO.
The results obtained are given in Table I here-under :

TABLE I

. ._ _ .... .. .~
20 Micro-organism Concen-tration Concentration of Strains PHMB ~oO-) Micro-organisms per ml Initial Final , ~ . _ . _ __ _ _. ~
Staphylococcus Aureus 0.15 10less than 105 Escherichia Coli 0.15 109 " " 105 Pseudomonas 9 6 A~lginosa 0.15 10more than 10 Sac~c~Dn~ 0.15 5, 10915. 10 . __ The drop in the micro-organism count is 104 C~PA~ATIV~ EX~PLE lB: - Testing -the fungicidal activity of PHMB -This product is not very active against mould and fungi~ It i,s necessary to use much higher concentrations.

~ ~433~

An inoculum is added to nutritious agar which is -then incubated for 4 or 5 days. PHM~ is added in a concentra-tion which will prevent growth.

_ . .. . ,~
Micro-organisms Concentration of PH~B
preventing grow~h (p~m) . , . ~. . . .. _ . . _ Aspergilus Niger 400 Penicill~m Nota-tum 1.5 Candida Albicans 250 COMPARATIVE EX~PLE lC: - Bactericidal ac-tivity of a quaternary ammonil~ compound such as didecvl dimethyl ammonium chloride -The procedure is the same as -that used in test lA
and the following resul-ts are obtained after one minute of exposure .
___ . . _~ _ _ ... _ .
Micro-organism Concentration Concen~ration of Strams of DDAC (~)micro-organisms per ml.
Initial Final - ~ . _.~ .__. ~ ~ __~
Streptococcus 0 . 03 5 ~106 3 ~103 Staphyloco ~ s Aureus 0.035 ~106 8 .103 Escherichia Coli 0.03 5~105 4'103 25 Pseudomonas 5 3 Aeruginosa 0 . 03 5 .10 10 . . _ _ _ _ . . _ _ _ . . . ~
The drop in bacterial concentration is only 103 after one minute.

EXAMPLE 1: - Bactericidal and fungicidal activi-ty of the compos-tion according to -the invention ~
The following solu-tion is prepared :
PHMB ............ ,......... 0...... 0.15%
DDAC ...................... ....... 0.03%
Ethanol at 90 .. S.Q.F. 100%
The bactericidal activity of this composi-tion is tested in vivo.
The results obtained after one minute of exposure are given in Table 4 hereunder.

_ .... . ~. . _ Micro-organism Micro-organism Co~t Strains Initial Final . . _ . _ . .. . . ~
S-taphylococcus ~ureus 6.106 o Escherichia Coli 5~1o6 Saccharomyces 7.106 o Total C~ws 20.10 5 There is consequently a decrease of the bacterial count of 106 in one minu-te.
This test proves -tha-t the activity of DDAC and of PHMB has strongly increased. The tested solution acts faster and stronger.
EXAMPLE 2:
.
The following solution is prepared :
PHMB in aqueous solu-tion at 20% .. .........Ø1 to 4%
DDAC in solution at 50% ........... A ~ 0~01 to 0.3%
Ethanol or water or mixture of both, s.O~F. 100%
This solution is used as a disinfec-tant for hospital staff, surgeons' hands, and various surfaces which may be contaminated, X-P~ay equipment, surgical instruments, etc.

3 3 ~

EXAMPLE 3:
The following solution is prepared :
PHMB in aqueous solution at 20% ................................ 20~
DDAC in solution at 50% .....Ø.......................... 1.5%
Distilled water ..............~........................... 100%
This composition used at 4% is one of the most powerful sterilants -Eor instruments.
EXAMPLE 4:
-An alcohol-free surgical soap is prepared as follows:
Mixture of amine oxides (lauryl, myristyl/ stearyl) at 30% of active materials....~............................ 21%
Thickening agen-t (polyethylene glycol distearate) 0.5-1%
Acetylated lanolin ...............,............................ 0.5%
PHMB in a~ueous solution at 20% .............. ~ ............ 1%
15 Alkyl dimethyl benzyl ammonium saccharinate in solution at 50% ............................... ........ 0.2%
Water ............................................ . S.~.F. 100%
The pH o-E this preparation is adjusted to between 6 and 7.
EXAMPLE 5:
... . .
A cleansing solution Eor skin and wounds is prepared as follows :
Amphoteric detergent ("Miranol") ........................ 15~
~3 PHMB in aqueous solution at 20% ........................ 1.5%
DDAC ......................~........................... 0.02%
Blue or pink dye and water in S.Q.F. 100%
The bactericidal activity of this composition i-~shown in Table 5 hereunder.

__ _ . .. _ . .. . .......... .
~ tial Micro organism Micro-organism count a~ter count Fer ml one minute exposure _ . _ ... . . . _ . .. _ . __ _ . __ l,S. 106 80
2,3. 106 90 ~ 1,7. lo , _ . ... ~ . _ ~r~Je ~c.~i 1 3 ~33~

A spray with long-lasting germicidal effect is prepared as follows :
PHMB (20%) ...................................... 1.5~
DDAC (50%) ..................................... 0.02%
Polyvinylpyrrolidone (MW 40,000).................... 2 Alcohol (70) ............................ S.Q.F. 100~
The bactericidal activity is tested according to GASHEN's method.
Three men and women wash their hands with soap for one minute. The soap is rinsed with water and the hand hands are air-dried. After 60 minutes~ a bacterial count is made on each hand and the germicidal solution is applied on each right hand, the left hand being used for control.
The following results are obtained :

TAsLE 6 _ _ ~
Initial bacterial I Final count count per ml. after one minute ~ . . ~
0.55.106 60 0.98.106 ~5 . ~ .... .~ _ Moreover, the bactericidal activity remains apparent after the wear of a surgical glove for one hour since the bacterial coun-t remains at the same level as immediately after the application of the disinfec-tant.
The residual activity for -this spray seems to be very good.
EXAMPLE 3:
A spraY is prepared as follows :
PHMB ~20%) .................................. 1 to 4%
Polyvinylpyrrolidone (MW 300,000 to 40,000) 0.5 to 2 1 3 3 .~-~

Quarternary ammon.ium compound ... O.......... ......Ø3~
Glutaraldehyde (in solution at 50%) ......... ...Ø5 - 2%
Water ....................................... S.Q.F. 100%
pH adjusted to between 6.5 and 6.8.
This product is used straight or diluted on contaminated surfaces. It destroys all the micro-organisms on the surface : gram positive and gram negat-ive bacteria, yeasts, viruses, and forms a thin film having a lasting germ-killing effect on micro-organisms present in the environment. It can be used as a cold sterilant for hemodyalyze internal circuits, steriliza-tion of surgical instruments~ probes; endoscopes, etc.
I-t destroys all micro-organisms, gram-~ and gram-bacteria, viruses, spores, fungi. The presence of poly-vinylpyrrolidone polymer confers the anti-redeposition properties to an aqueous solution and thus any soils removed remain in suspension without depositing on the surface.

Claims (5)

The embodiments of the invention in which an exclusive property or privilege is claimed are defined as follows:
1. A novel bactericidal and fungicidal composition con-taining polymeric hexamethylene biguanide hydrochloride (PHMB) and a quaternary ammonium compound, the quaternary ammonium compound being didecyl dimethyl ammonium chloride (DDAC), the amount of PHMB being from 0.1 to 4% and the amount of DDAC being from 0.01 to 1.5%.
2. The composition of claim 1 wherein said composition is an alcoholic solution.
3. The composition of claim 1 wherein said composition is an aqueous solution.
4. The composition of any one of claims 1, 2 or 3, which contains in addition a film forming polymer.
5. The composition of any one of claims 1, 2 or 3, which contains in addition a film forming polymer and wherein the polymer is polyvinylpyrrolidone having a molecular weight of 300,000 to 40,000.
CA000378586A 1980-05-29 1981-05-28 Disinfectant composition containing a quaternary ammonium and a polymer of hexamethylene beguanide hydrochloride Expired CA1164338A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
FR8011892A FR2483177A1 (en) 1980-05-29 1980-05-29 NOVEL DISINFECTANT COMPOSITION COMPRISING A QUATERNARY AMMONIUM AND A HEXAMETHYLENE BIGUANIDE HYDROCHLORIDE OLIGOMER
FR8011892 1980-05-29

Publications (1)

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CA1164338A true CA1164338A (en) 1984-03-27

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Country Status (8)

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EP (1) EP0041448B1 (en)
JP (1) JPS5746906A (en)
AT (1) ATE10697T1 (en)
AU (1) AU7098381A (en)
CA (1) CA1164338A (en)
DE (1) DE3167689D1 (en)
FR (1) FR2483177A1 (en)
ZA (1) ZA813565B (en)

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WO2017222963A1 (en) * 2016-06-24 2017-12-28 Lonza Inc. Synergistic antimicrobial combinations containing quaternary ammonium biocide

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CA1259542A (en) * 1984-09-28 1989-09-19 Francis X. Smith Disinfecting and preserving solutions for contact lenses and methods of use
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US7759327B2 (en) 2006-01-06 2010-07-20 The Trustees Of Columbia University In The City Of New York Compositions containing zinc salts for coating medical articles
EP2359690A1 (en) 2010-02-23 2011-08-24 East Coast Pharmaceutical Research LLC Multiplication of the effectiveness of anti-infective agents by a composition including both a dispersant agent and a metal reversal agent
CA2819137C (en) 2010-12-14 2020-04-28 Ecolab Usa Inc. Wear resistant antimicrobial compositions comprising a quaternary ammonium compound and a cationic biocide, and methods of use thereof
JP5837346B2 (en) * 2011-07-05 2015-12-24 攝津製油株式会社 Virus inactivating composition
RU2589835C1 (en) * 2015-04-29 2016-07-10 Общество с ограниченной ответственностью "Международный институт эколого-технологических проблем" Disinfectant
CN105839410A (en) * 2016-03-29 2016-08-10 腾科宝迪(厦门)生物科技有限公司 Safety protection surgical gown
CN111450001A (en) * 2020-04-14 2020-07-28 广东润洁日化有限公司 Hand cream with antibacterial effect and preparation method thereof

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Publication number Priority date Publication date Assignee Title
WO2017222963A1 (en) * 2016-06-24 2017-12-28 Lonza Inc. Synergistic antimicrobial combinations containing quaternary ammonium biocide

Also Published As

Publication number Publication date
EP0041448A1 (en) 1981-12-09
FR2483177A1 (en) 1981-12-04
AU7098381A (en) 1981-12-03
DE3167689D1 (en) 1985-01-24
JPS5746906A (en) 1982-03-17
EP0041448B1 (en) 1984-12-12
ATE10697T1 (en) 1984-12-15
ZA813565B (en) 1982-06-30

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