AU2014221288A1 - Disinfectant - Google Patents

Abstract

The invention relates to a disinfectant composition comprising a) a quaternary ammonium salt of the general formula (Ib) and optionally, an amine of the general formula (Ia) where R' is C6 -1 -alkyl, R2 is benzyl or C 6-1 -alkyl, R3 is C 1 i-alkyl or -[(CH 2 )2-O1 R6 where n = 1 20, R 4 and R5 independently of one another are C 1 4 -alkyl, R6 is hydrogen or unsubstituted or substituted phenyl, and A is a monovalent anion or one equivalent of a polyvalent anion of an inorganic or organic acid; and b) at least one alkanolamine of the general formula (II), where m and, if present, o and p independently of one another have the value 2 or 3, and x and y independently of one another have the value 0 or 1, or a corresponding salt; in the mass ratio (I) :(II) of 20:1 to 1:20. Compositions of the invention may find application as bactericidal and/or fungicidal agents suitable for use as both disinfectants and preservative agents.

Description

EDITORIAL NOTE 2014221288 - There are 9 pages of Description - The 1 st page starts with page numbering beginning on "2", (refer to divisional parent) 2 Disinfectant The present application is a divisional application from Australian Patent Application No. 2012203225, which in turn is a divisional 5 application of Australian Patent Application No. 2008243248, which in turn is a divisional application of Australian patent application number 2006203306, which is in turn a divisional application of Australian patent application number 2002221601, the entire disclosure of the applications being incorporated herein by 10 reference. The invention relates to synergistic disinfectant compositions based on amines and/or quaternary ammonium salts. Numerous disinfectant and preservative compositions based on amines and/or quaternary ammonium salts are known. However, in general, in 15 particular at relatively high dilution, these exhibit an unsatisfactory activity towards fungi, for example Aspergillus niger. It was therefore an aspect of the present invention to provide disinfectant compositions based on amines and/or quaternary ammonium salts which exhibit good activity towards fungi even at high 20 dilution. This aspect is achieved according to the invention by the disinfectant composition according to Claim 1. It has surprisingly been found that amines and/or quaternary ammonium salts of the general formula R-N Qa) or R h-R A ) (Cit)NH 25 where R' is C 6

-

1 -alkyl R2 is benzyl or C 6

-

1 -alkyl R3 is C1_ 13 -alkyl or -[ (CH2) 2 -O]nR 6 where n = 1-20

R

4 and R 5 independently of one another are C 1

_

4 -alkyl 30 R 6 is hydrogen or unsubstituted or substituted phenyl and A is a monovalent anion or one equivalent of a polyvalent anion of an inorganic or organic acid; by addition of at least one alkanolamine of the general 3 formula CH2)60tH HO{CH2 (CH2)O H where m and, if present, o and p independently of one another have the value 2 or 3 5 and x and y independently of one another have the value 0 or 1, or a corresponding salt; in the mass ratio (I):(II) of 20:1 to 1:20 obtain good fungicidal activity. In another aspect, the present invention provides use of a 10 disinfectant composition comprising as the active ingredients a) a quaternary ammonium salt (Ib) selected from the group consisting of didecyldimethylammonium salts, dioctyldimethylammonium salts, octyldecyldimethylammonium salts, benzyldimethyl oxoethylammonium salts, and mixtures of these compounds, 15 b) at least one alkanolamine (II) selected from the group consisting of monoethanolamine, diethanolamine, and 3-amino-1 propanol, and, optionally, an amine (Ia) selected from the group consisting of N,N-bis (3-aminopropyl) dodecylamine and N,N-bis (3 20 aminopropyl)octylamine, in the mass ratio of ((Ib)+(Ia)):(II) of 1:5 to 5:1 as a disinfectant against fungi. In another aspect, the present invention provides a disinfectant 25 composition when used for surface disinfection, instrument disinfection, laundry disinfection, hand disinfection or in chemical toilets against fungi; wherein the disinfectant composition comprises as the active ingredients a) a quaternary ammonium salt (Ib) selected from the group 30 consisting of didecyldimethylammonium salts, dioctyldimethylammonium salts, octyldecyldimethylammonium salts, benzyldimethyl oxoethylammonium salts, and mixtures of these compounds, 3a b) at least one alkanolamine (II) selected from the group consisting of monoethanolamine, diethanolamine, and 3-amino-1 propanol, 5 and, optionally, an amine (Ia) selected from the group consisting of N,N-bis (3-aminopropyl) dodecylamine and N,N-bis (3 aminopropyl)octylamine, in the mass ratio of ((Ib)+(Ia)):(II) of 1:5 to 5:1. 10 An embodiment of the invention is a disinfectant composition comprising a) a quaternary ammonium salt of the general formula P-N- A (ro), R and optionally, an amine of the general formula R-N() IIa (CHal)NH 2 15 where R is C 6

-

1 -alkyl, R2 is benzyl or C 6

-

1 -alkyl, R3 is C1_ 1 3 -alkyl or -[(CH2) 2

-O]R

6 where n = 1-20, R 4 and R 5 independently of one another are C1_ 4 -alkyl, R 6 is hydrogen or unsubstituted or substituted phenyl, and A is a monovalent anion or one equivalent of a polyvalent anion 20 of an inorganic or organic acid; and b) at least one alkanolamine of the general formula HO-(C )1( t (UR where m and, if present, o and p independently of one 25 4 another have the value 2 or 3, and x and y independently of one another have the value 0 or 1, or a corresponding salt; in the mass ratio (I):(II) of 20:1 to 1:20. 5 Alkyl, as used herein, is taken to mean in each case unbranched or branched alkyl groups of the specified number of carbons, but preferably unbranched alkyl groups, and particularly preferably those having an even number of carbon atoms. In particular, this is also taken to mean the 10 homologue mixtures derived from natural raw materials, for example "coconutalkyl". Substituted phenyl is taken to mean, in particular, phenyl groups substituted with one or more C 1

.

8 -alkyl groups and/or 15 chlorine atoms. Suitable anions A- are in principle all inorganic or organic anions, in particular halide, for example chloride or bromide, or anions of low carboxylic acids, for example 20 acetate, propionate or lactate. The amine or quaternary ammonium salt (Ia/Ib) is preferably N, N-bis (3-aminopropyl) dodecylamine, N,N-bis (3-aminopropyl)octylamine, a didecyldimethylammonium salt, 25 dioctyldimethylammonium salt, octyldecyldimethylammonium salt, dicoconutalkyldimethylammonium salt, coconutalkyldimethylpoly (oxyethyl) ammonium salt, dicoconutalkylmethylpoly (oxyethyl) ammonium salt, decyl dimethylpoly (oxyethyl) ammonium salt, didecylmethyl 30 poly(oxyethyl) ammonium salt, octyldimethylpoly(oxy ethyl) ammonium salt, dioctylmethylpoly (oxyethyl) ammonium salt, coconutalkyldimethylbenzylammonium salt, benzyldodecyldimethylammonium salt or benzyldimethyl poly (oxyethyl) ammonium salt or a mixture of two or more of 35 these compounds. Suitable alkanolamines (II) are in principle all ethanolamines and propanolamines, in particular mono ethanolamine, diethanolamine, triethanolamine and 3-amino- 5 1-propanol. Obviously, using mixtures of the said compounds is also within the scope of the invention. Particularly good results have been obtained using the compounds having a primary amino group, that is to say using monoethanolamine 5 and 3-amino-1-propanol. The mass ratio of amine (Ia) or quaternary ammonium salt (Ib) to alkanolamine (II) is preferably in the range from 1:5 to 5:1. 10 The inventive disinfectant compositions preferably comprise water as solvent, if appropriate in combination with an organic solvent. 15 Preferably, the inventive disinfectant compositions further comprise one or more aids selected from the group consisting of organic solvents, surfactants, complexing agents, fragrances and colorants. 20 A preferred field of application of the inventive disinfectant compositions is surface disinfection and instrument disinfection. Further preferred fields of application are laundry 25 disinfection and hand disinfection. The inventive disinfectant compositions are also suitable for use in chemical toilets, for example on board aircraft and vehicles. 30 A further preferred field of use is the preservation of industrial liquids, for example water circulation in paper manufacturing, cooling water, belt lubricants for conveyor belts, or cutting fluids in metal machining. 35 An application which is likewise preferred is finally the use as preservative for construction materials which are organic or susceptible to biological attack, for example wood.

6 The discussion of the background of the invention herein is included to explain the context of the invention. This is not to be taken as an admission that any of the material 5 referred to was published, known or part of the common general knowledge in Australia as at the priority date of any of the claims. Throughout the description and the claims of this 10 specification the word "comprise" and variations of the word, such as "comprising" and "comprises" is not intended to exclude other additives, components, integers or steps. The examples below illustrate the implementation of the 15 invention, and should not be taken to be a restriction to the embodiments described. All quantities given, where not otherwise specified, are in % by mass. The test microorganism used in each case was Aspergillus niger ATCC 16404. The effectiveness was determined, unless 20 otherwise specified, using the method specified in CEN 1275, Example 1 A disinfecting cleaner formulation (concentrate) was 25 prepared from: 5.0% didecyldimethylammonium chloride (50% strength solution) 2.0% N,N-bis (3-aminopropyl) dodecylamine 30 5.0% monoethanolamine 5.0% Genapol T250 (tallow fatty alcohol polyglycol ether, 25 mol of ethylene oxide) 0.5% sodium metasilicate 0.5% sodium carbonate 35 2.0% methylglycinediacetic acid trisodium salt (Trilon* M; 40% strength solution) water to 100% The effectiveness was determined using a dilution (1 part of 7 concentrate, 99 parts of water) at 200C and with a contact time of 15 min. The logarithm to base ten of the reduction in microorganism count was 4.1. 5 Comparative Example 1 The procedure of Example 1 was followed, but with the difference that the monoethanolamine was replaced by the same amount of water. Under the same test conditions, the 10 formulation was virtually inactive. Example 2 A disinfectant formulation (concentrate) was prepared from: 15 4.9% N,N-bis (3-aminopropyl) dodecylamine 4.0% monoethanolamine 2.0% Genapole T250 (tallow fatty alcohol polyglycol ether, 25 mol of ethylene oxide) 20 5.0% Hostapur SAS 30 (C13-17 secondary n-alkanesulphonic acid, sodium salt) 2.0% ethylenediaminetetraacetic acid tetrasodium salt (40% strength solution) 0.7% ethylenediaminetetraacetic acid 25 water to 100% The effectiveness was determined using a dilution (1 part of concentrate, 199 parts of water) at 200C and with a contact time of 15 min. The logarithm to base ten of the reduction 30 in microorganism count was 4.3. Example 3 A disinfectant formulation (concentrate) was prepared from: 35 4.2% N,N-bis (3-aminopropyl) dodecylamine 2.0% didecylmethylpoly(oxyethyl) ammonium propionate (BARDAP 26) 4 . 0% monoethanolamine 8 2.0% Genapole T250 (tallow fatty alcohol polyglycol ether, 25 mol of ethylene oxide) 5.0% Hostapur SAS 30 (C 13

..

17 secondary n-alkanesulphonic acid, sodium salt) 5 2.0% ethylenediaminetetraacetic acid tetrasodium salt (40% strength solution) 0.7% ethylenediaminetetraacetic acid 4.0% butyl diglycol water to 100% 10 The effectiveness was determined using a dilution (1 part of concentrate, 199 parts of water) at 20 0 C and with a contact time of 15 min. The logarithm to base ten of the reduction in microorganism count was > 4.4. 15 In addition, the effectiveness was also determined using the method specified in CEN 1650 with a contact time of 15 min, a concentration of 1.0%, a water hardness of 30 0 fH and an organic load of 0.3% albumin. The logarithm of the reduction in microorganism count was > 4.4. 20 Examples 4-19 Aqueous solutions were prepared from 0.5% alkanolamine (II) and 0.25% of amine or quaternary ammonium salt (Ia/Ib) and 25 tested using the method specified in CEN 1275. The results are summarized in Table 1.

9 Table I Example Amine/ammonium salt Alkanolamine log microbial reduction 4 dimethyldioctyl- monoethanolamine 4.3 ammonium chloride 5 ditto diethanolamine 4.0 6 ditto triethanolamine 3.6 7 ditto 3-amino- 4.2 1-propanol 8 didecyldimethyl- monoethanolamine 4.0 ammonium chloride 9 ditto diethanolamine 3.8 10 ditto triethanolamine 3.1 11 ditto 3-amino- 4.0 1-propanol 12 di-Cso-alkyldimethyl- monoethanolamine 3.9 ammonium chloride (60%) /C1 2 .6-alkyl benzyldimethylammonium chloride (40%) Bardac* 205-M 13 ditto diethanolamine 3.2 14 ditto triethanolamine 2.8 15 ditto 3-amino- 3.8 1-propanol 16 N,N-bis(3-amino- monoethanolamine 2.9 propyl) dodecylamine 17 ditto diethanolamine 2.7 18 ditto triethanolamine 2.4 19 ditto 3-amino- 2.8 1 -propanol For comparison, all compounds listed in Table 1 were tested 5 as individual substances in 0.5% strength solution. None of these compounds exhibited pronounced fungicidal activity (log microbial reduction < 2).

Claims (22)

1. Disinfectant composition comprising a) a quaternary ammonium salt of the general formula R and optionally, an amine of the general formula R-N (CHQNH 2 where R' is C 6 - 1 -alkyl R2 is benzyl or C 6 - 1 -alkyl R3 is C> 1 -alkyl or -[ (CH2) 2 -O]R6 where n = 1-20 R 4 and R 5 independently of one another are C 1 _ 4 -alkyl R 6 is hydrogen or unsubstituted or substituted phenyl and A is a monovalent anion or one equivalent of a polyvalent anion of an inorganic or organic acid; and b) at least one alkanolamine of the general formula where m and, if present, o and p independently of one another have the value 2 or 3 and x and y independently of one another have the value 0 or 1, or a corresponding salt; in the mass ratio (I):(II) of 20:1 to 1:20.

2. Disinfectant composition according to Claim 1, wherein the quaternary ammonium salt (Ib) is selected from the group consisting of didecyldimethylammonium salts, 11 dioctyldimethylammonium salts, octyldecyldimethylammonium salts, coconutalkyldimethylbenzylammonium salts and benzyldimethyloxoethylammonium salts and mixtures of these compounds; and the optional amine (Ia) is selected from the group consisting of: NN-bis(3-aminopropyl)dodecylamine and N,N-bis (3-aminopropyl) octylamine.

3. Disinfectant composition according to Claim 1 or 2, wherein the alkanolamine (II) is selected from the group consisting of mono-ethanolamine, diethanolamine, triethanolamine and 3-amino 1-propanol.

4. Disinfectant composition according to any one of Claims 1 to 3, wherein the mass ratio (I):(II) is between 1:5 and 5:1.

5. Disinfectant composition according to any one of Claims 1 to 4, wherein it comprises water as a solvent.

6. Disinfectant composition according to any one of Claims 1 to 5, wherein it additionally comprises one or more aids selected from the group consisting of organic solvents, surfactants, complexing agents, fragrances and colorants.

7. Use of the disinfectant composition according to any one of Claims 1 to 6 for surface disinfection and instrument disinfection.

8. Use of the disinfectant compositions according to any one of Claims 1 to 6 for laundry disinfection.

9. Use of the disinfectant compositions according to any one of Claims 1 to 6 for hand disinfection.

10. Use of the disinfectant composition according to any one of Claims 1 to 6 in chemical toilets. 12

11. Use of the disinfectant compositions according to any one of Claims 1 to 6 as preservatives for industrial liquids.

12. Use of the disinfectant composition according to any one of Claims 1 to 6 as preservatives for construction materials.

13. Use of a disinfectant composition comprising as the active ingredients a) a quaternary ammonium salt (Ib) selected from the group consisting of didecyldimethylammonium salts, dioctyldimethylammonium salts, octyldecyldimethylammonium salts, benzyldimethyl-oxoethylammonium salts, and mixtures of these compounds, b) at least one alkanolamine (II) selected from the group consisting of monoethanolamine, diethanolamine, and 3-amino 1-propanol, and, optionally, an amine (Ia) selected from the group consisting of NN-bis(3-aminopropyl)dodecylamine and NN-bis(3 aminopropyl)octylamine, in the mass ratio of ((Ib)+(Ia)):(II) of 1:5 to 5:1 as a disinfectant against fungi.

14. Use according to Claim 13, wherein the disinfectant composition further comprises water as a solvent.

15. Use according to Claim 13 or Claim 14, wherein the disinfectant composition further comprises one or more aids selected from the group consisting of organic solvents, surfactants, complexing agents, fragrances and colorants.

16. Use according to any one of Claims 13 to 15 for surface disinfection and instrument disinfection.

17. Use according to any one of Claims 13 to 15 for laundry disinfection. 13

18. Use according to any one of Claims 13 to 15 for hand disinfection.

19. Use according to any one of Claims 13 to 15 in chemical toilets.

20. A disinfectant composition when used for surface disinfection, instrument disinfection, laundry disinfection, hand disinfection or in chemical toilets against fungi; wherein the disinfectant composition comprises as the active ingredients a) a quaternary ammonium salt (Ib) selected from the group consisting of didecyldimethylammonium salts, dioctyldimethylammonium salts, octyldecyldimethylammonium salts, benzyldimethyl-oxoethylammonium salts, and mixtures of these compounds, b) at least one alkanolamine (II) selected from the group consisting of monoethanolamine, diethanolamine, and 3-amino 1-propanol, and, optionally, an amine (Ia) selected from the group consisting of N,N-bis(3-aminopropyl)dodecylamine and N,N-bis(3 aminopropyl)octylamine, in the mass ratio of ((Ib)+(Ia)):(II) of 1:5 to 5:1.

21. The disinfectant composition according to claim 20, further comprising water as a solvent.

22. The disinfectant composition according to Claim 20 or Claim 21 further comprising one or more aids selected from the group consisting of organic solvents, surfactants, complexing agents, fragrances and colorants.