antibacterial wipes

I am not planning to try to compete with low cost commercial produts, but had this thought: is there any reason why a low % of cetrimonium chloride should not be as efficient as the benzalkonium chloride I see on ingredient lists?
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  • letsalcidoletsalcido Member
    edited June 4
    I had the same thought! Not for making a commercial product but for a surface cleaner/degreaser (e.g. formula 409) for my own household.

    The molecules are quite different however. 
    Cetrimonium:
    Benzalkonium:


    I get the sense that the benzene ring may play a role or increase the membrane destabilizing/denaturing effect so less of it is needed. Therefore a higher concentration of cetrimonium chloride would be sufficient, but then it increases the risk of irritation or other adverse effects. If you have the means to test efficacy and compare (even if on a rudimentary way) I would love to hear what you find.

    Maybe someone with a strong pharmacology background has an explanation why many biologically active ingredients have a benzene ring or are cyclic, and if this could play a role in why benzalkonium is more potent than cetrimonium.
  • BelassiBelassi Member
    Yes, I've also been wondering about making an antibacterial soap using it, (and amphoteric surfactants).
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  • PharmaPharma Member, Pharmacist
    ...
    Maybe someone with a strong pharmacology background has an explanation why many biologically active ingredients have a benzene ring or are cyclic, and if this could play a role in why benzalkonium is more potent than cetrimonium.
    Pharmacology doesn't really apply here, we're hopefully not going to treat microbes so they feel better and live longer :blush: .
    We're also not interested in 'biological activity' (and there are several reasons including chemical universe and patents, not just biology) and hence, such aspects do not apply to disinfectant activities (they may apply to antibiotic activities but that's also not what we're looking at here). Not to speak of microbes being VERY different from human bodies. A lot with disinfectants are empirical findings and speculations on the how & why resulting in rules of thumb.
    The benzene ring does indeed increase affinity for cell membranes and DNA/RNA and also disturbs more due to a larger head group. The special influence/interaction of aromatic rings with surfactant layers (simply put, cell membranes are exactly that) or more precisely the interphase between water and oil is a known phenomenon but we don't know why or how.
  • @Pharma thanks for the input. I mentioned pharmacology for the lack of knowledge of a better word. I figured pharmacology is concerned since this is labeled as an active drug ingredient in antiseptic solutions for treating wounds.

    It does make sense that it may not be concerned about this compound as it’s mechanism of action is not similar to, let’s say, an enzyme inhibitor (like triclosan) that targets a specific pathway nor is it consumed.

    This is interesting though, I would assume (perhaps erroneously) that like any other denaturants (alcohol, heat...), it’s not as easy to develop resistance to them. So, this and similar compounds are a better alternative for disinfecting solutions than other compounds with affinities to a specific binding site.

    @Belassi I was doing some research and found this https://www.ncbi.nlm.nih.gov/pmc/articles/PMC88911/, it seems like the bromide salt is preferred over chloride as biocide. It also mentions some of these QAC don’t destabilize the membrane enough on their own to cause cell lysis, so the solution needs to be hypotonic. Of course, with addition of other detergents in your formulation it may be enough. 

    I can’t seem to find any research on cetrimonium chloride’s biocidal activity or concentrations used for that effect.
  • PharmaPharma Member, Pharmacist
    ...
    This is interesting though, I would assume (perhaps erroneously) that like any other denaturants (alcohol, heat...), it’s not as easy to develop resistance to them. So, this and similar compounds are a better alternative for disinfecting solutions than other compounds with affinities to a specific binding site...
    QACs are less likely to lead to resistance but microbes are a crafty little folk and find their way around nearly everything thrown at them, even QACs. However, such mechanisms are more difficult and often involve more steps (e.g. changing cell wall composition) and a higher energy demand (e.g. efflux pumps, 'detox' metabolism) than simply modifying a binding site with a more or less free of charge SNP.
  • @Pharma agreed, my train of thought exactly.

    Thanks for the input!
  • BelassiBelassi Member
    I think to amuse myself I will see if I can design an antibacterial liquid soap. Let's see... sodium cocoamphoacetate, that's got nice foam. CAPB of course. I'll start with just those two. For fragrance, 0.1% lavender EO will add some antibacterial function too (the MIC for it is 0.1%). Hmm... glycerin, 1% PEG7GC, citric acid to lower the pH, do I really need a preservative given that I'm going to add CETAC? Maybe against mould. So 0.3% sodium benzoate then.
    How much CETAC? There's the question. HELP!
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  • MarkBroussardMarkBroussard Member, Professional Chemist
    @Belassi:

    1% to 2% CETAC should do the trick.  But, CETAC is not nearly as effective an antimicrobial as Benzalkonium Chloride ( use level is 0.10% to .12% ) and the CETAC does make the product sticky, but perhaps not so much in an antibacterial liquid soap.
    Chemist/Microbiologist formulating in the Organic & Naturals arena under ECOCert/Natural Products Assn/Whole Foods/National Organic Program guidelines focused skincare & haircare products. 

    See website for details www.desertinbloomcosmeticslab.com
  • BelassiBelassi Member
    Thank you - I'll try this and report back. Problems at the moment, we are moving imminently and 95% of lab materials are already packed. I am seriously worried about all the glassware, I hope I packed it well enough.
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  • @Belassi good luck with your move!

    @MarkBroussard thanks for the tip! Do you happen to know of any documentation/papers on the effectiveness at different concentrations?
  • MarkBroussardMarkBroussard Member, Professional Chemist
    @letsalcido:

    That I do not. Obviously, there have been lots of projects for hand sanitizers the past few months.  I made BenzAlk sanitizer prototypes with and without CETAC is how I know the skin sensorial gets unacceptable above 1% or so.  Much easier and more effective to just use BenzAlk, imho.
    Chemist/Microbiologist formulating in the Organic & Naturals arena under ECOCert/Natural Products Assn/Whole Foods/National Organic Program guidelines focused skincare & haircare products. 

    See website for details www.desertinbloomcosmeticslab.com
  • Cafe33Cafe33 Member
    edited June 8
    I just made a first sample of an antimicrobial hand soap/Shampoo. It was done in haste, specifically to test the carbopol Aqua SF1 I just received.

    SLES - 28% (29% active)
    CAPB - 15% (30% active)
    Carbopol SF1 - 4.0 % (1.2% active)
    Triet. - 1.2%

    EDTA - 0.15% 
    Polyquat 7 - 1.00% 
    Purple Mica - 0.15 %
    BenzAlk - 0.23% (too high I know)
    Fragrance - 0.1% 
    Germall Plus - 0.5%

    Viscocity is excellent. Better than expected with the minimum amount of suggested Carbopol. No Salt or Back Acid titration was used so far.  

    I wonder if the BenzAlk and Polyquat are compatible with a SLES-CAPB-Salt system without the carbopol?

    At what percentage would the BenzAlk be self preserving?

  • ChiragChirag Member
    @Cafe33 u think you need not to use  Benzalkonium chloride here as you are already using grrmall Plus. Above this , benzalkonium won't go right with SLES as both are opposite in polarities.. 
    My thoughts..Welcome for  any corrections
  • Cafe33Cafe33 Member
    edited June 9
    Thank you Chirag. I will eliminate any additional preservative. Thats what I thought but was unsure.

    From the literature on Carbopol SF-1

    Cationic Surfactants

    As a general rule, cationic surfactants may have limited compatibility with Carbopol Aqua SF-1 polymer. Low levels of cetrimonium chloride have been shown to be compatible with the polymer in a shampoo formulation. 

    https://www.ict.unesp.br/Home/sobreoict/departamentosdeensino/odontologiarestauradora/lipq-laboratoriointegradodepesquisa/carbopol-aqua-sfi-ilovepdf-compressed.pdf

    So would this apply to benzalkonium? I would imagine a low level of Cetrimonium Chloride would be 0.3%. So perhaps 0.10-0.12% Benzalkonium Chloride would be compatible? Any thoughts?
  • @Cafe33 it’s not just the carbopol that’s the issue.  The positive charge on benzalkonium chloride and cetrimonium chloride will interact with the negative charge on SLES and will probably render the cationics useless.

    Cationic surfactants rely on electrostatic forces to work, it increases their affinity for cell membranes (and hair/surfaces), when you neutralize that force you lose the benefits. That’s why you should use amphoterics or non-ionics with cationics.
  • BelassiBelassi Member
    edited June 9
    Yes, that's why I am proposing to use only amphoterics or non-ionic surfactants. Possibly D-limonene in a small percentage would also add antibacterial activity, it's a good solvent, after all. Must check.
    *EDIT* "d-Limonene showed a MIC equal to 256 μg/mL against standard S. aureus and 512 μg/mL against resistant P. aeruginosa."
    - that's pretty decent! Like, 0.0005% is the minimum inhibitory concentration! Why not use say, 0.01% then? That's 20 times the MIC.
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  • @Belassi ;I didn’t know that about d-limonene, but this is great to know. I wanted to somehow incorporate orange essential oil into my antibacterial surface cleaner. The EO I have said it was 90% limonene, so who knew I would kill two birds with one stone.
  • Cafe33Cafe33 Member
    edited June 9
    Okay yes, I was so enthusiastic about trying this form of Carbopol that I misinterpreted the term compatibility. The Lubrizol document is talking about compatibility in the sense of stability not mode of action. 

    An excerpt from Antisepsis, disinfection, and sterilization / Gerald E. McDonnell:

    "The antimicrobial efficacy of QACs can be negatively affected in the presence of hard water (if in a diluted product), fatty materials, and anionic surfactants (including soaps); this varies depending on the QAC type and formulation."

    So maybe Belassi's suggestion of D-Limonene would help the efficacy of soap in a multitude of ways. 

    I have some Decyl Glucoside, I wonder what would be an appropriate amount to use alongside CAPB.
  • @Cafe33 a lot of commercial brands use D-limonene in antibacterial wipes, so I’m sure it at least doesn’t interfere with QACs at the percentages they use.

    Decyl glucoside should work great, and would help solubilize your EOs too. I don’t have enough experience to say what ratio of CAPB to use with Decyl Glucoside, but you can always just experiment and see.


  • Cafe33Cafe33 Member
    edited June 9
    BAC is quite a good solubillizer on its own from my (limited) experience.

    I have straight Decyl Glucoside as well as Plantapon TF (Decyl Glucoside, Polyglyceryl-10 Caprylate/Caprate, Coco-Glucoside and Glyceryl Oleate). The foaming with this blend is not all that great.

    The Plantapon has an acidic pH since it contains some citric pH, most likely not compatible with our active?

    What should be the target pH for a final product containing Benzalkonium? 


  • Bill_TogeBill_Toge Member, Professional Chemist
    edited June 9
    apropos of nothing, a few years ago Dettol sold a BAC-containing handwash based on cationic surfactants; I believe they used cetrimonium chloride as a primary surfactant and cocamide DEA as a thickener/foam booster, and the lack of decent alternatives made it difficult to replicate their product without treading on the toes of their patent
    interestingly, the BAC in that product was above the maximum permitted limit for use in cosmetics as a preservative, so it's very likely they were selling it as a human-use biocide
    UK based formulation chemist. Strongest subjects: hair styling, hair bleaches, hair dyes (oxidative and non-oxidative) I know some stuff about: EU regulations, emulsions (O/W and W/O), toothpaste, mouthwash, shampoos, other toiletries
  • BelassiBelassi Member
    That's interesting, Bill.
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  • BelassiBelassi Member
    Increasingly, here. it is becoming evident that the bottles of sanitiser contain little or no alcohol. How annoying.
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  • Cafe33Cafe33 Member
    Yes Belassi, there is even a video of company trying to sell their gel by showing that it is not flammable. They claim there is a fire retardant of some kind.

  • PharmaPharma Member, Pharmacist
    Cafe33 said:
    ...They claim there is a fire retardant of some kind.
    Fire retardant? Hmm... water comes to mind :smile: ...

  • Cafe33Cafe33 Member
    Ha, exactly. What is frightening is that this was a presentation for a purchasing manager at a big box (american) store. The quote was for 60,000L of Alcohol hand sanitizer. We lost the bid. 

    The video they sent the purchasing manager is a demonstration of their gel vs another brand. One can be ignited with a flame, and other one does not catch on fire. That was the selling point.

    What is really frightening is that I recognized the brand on the shelves of a nationwide pharmacy chain. It is a real mess. 

    Luckily, there is a large shipment of corn based Alcohol coming from the USA and it has brought down the price significantly. We will see if that changes the tide. 
  • Cafe33Cafe33 Member
    Tried the following formulation 

    10 % Decyl Glucoside
    15 % CAPB (30% active)
    2% Cocamide DEA

    4% Carbopol Aqua SF1

    2.5% Polyquat 7
    0.12% BAC

    Too viscous, almost paste-like. Great, smooth hand feel however hardly any foam. I will drop the Polyquat 7 to 2.0%. I will also test this formulation without thickener. Waiting on EDTA 4Na. Hopefully that will boost the foam.  
  • BelassiBelassi Member
    Very interesting.
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  • Cafe33Cafe33 Member
    edited June 12
    Tried the following:

    10 % Decyl Glucoside
    15 % CAPB (30% active)
    2% Cocamide DEA

    2.0% Polyquat 7
    0.12% BAC

    Clear gel, no rheology modifier. I like Polyquat at 2.0%, significant improvement over 1.0% and similar to 2.5%. 

    Viscosity needs improvement but not by much. Product "rinsability" is not as good, can leave a slight sticky feel between fingers if hands not rubbed vigorously enough. Hopefully the EDTA 4 Na will help. 
  • BelassiBelassi Member
    The Decyl is non-ionic, I don't stock that... I'll try an alternative then, I've got Dehyton G, that's amphoteric, so I'll try 10% sodium cocoamphoacetate instead. What's causing the sticky feel? 
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  • Cafe33Cafe33 Member
    The same surfactant formulation using Carbopol SF-1 did not give a sticky feel. It does seem to "spread" and rinse-off as easily on the hand.  
  • BelassiBelassi Member
    What change did you make?

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  • Cafe33Cafe33 Member
    I knocked out the Carbopol SF-1. I will be attempting another formulation with half the amount of Carbopol. Lubrizol recommends 4.0% min but I think that is not needed with this formulation. 
  • BelassiBelassi Member
    Well, that's good news! SF-1 is not cheap.
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  • Cafe33Cafe33 Member
    edited June 19
    So 2.0 % Carbopol Aqua SF-1 is sufficient to thicken this formulation. I don't think I would go lower.

    10 % Decyl Glucoside
    15 % CAPB (30% active)
    2% Cocamide DEA

    2% Carbopol Aqua SF1

    0.20% EDTA 4 Na
    2.0% Polyquat 7
    0.12% BAC

    Great hand feel, doesn't run off on hands, no stickiness and rinses off well. 

    I noticed quite a loss of viscosity when adding the Polyquat 7. I will play with the percentage between 1.0-2.0% to find a proper target amount. I will also knockout the Cocamide DEA to see if I can remove it altogether.
  • BelassiBelassi Member
    I will also knockout the Cocamide DEA to see if I can remove it altogether.
    -- But isn't that what's neutralising the SF-1?
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  • Cafe33Cafe33 Member
    My apologies, I posted an incomplete formulation.

    In order of addition:

    2% Carbopol Aqua SF1
    40% dH20
    0.6 % Triethanolamine

    10 % Decyl Glucoside
    15 % CAPB (30% active)
    2% Cocamide DEA

    0.20% EDTA 4 Na
    2.0% Polyquat 7
    0.12% BAC
    0.10 % Fragrance (Lemon grass EO)
    Trace color (unmeasured)

    Water to qs

    I will try to remove Cocamide DEA, reduce Polyquat 7 and possibly reduce Decyl Glucoside (cost issue.) I have not monitored pH at this stage (laziness) but will start to do so as well,   

  • BelassiBelassi Member
    Sounds good to me. I understand now. I had assumed the high pH DEA was being used to neutralise the carbomer. It's a pity I can't yet cooperate on development, my lab is in lots of cardboard boxes and plastic dewars, right now.
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  • Cafe33Cafe33 Member
    So I knocked out the Cocamide DEA from this formulation:

    2% Carbopol Aqua SF1
    40% dH20
    0.6 % Triethanolamine

    10 % Decyl Glucoside
    15 % CAPB (30% active)

    2% Cocamide DEA

    0.20% EDTA 4 Na
    2.0% Polyquat 7
    0.12% BAC
    0.10 % Fragrance (Lemon grass EO)
    Trace color (unmeasured)


    Terrible idea. Milky and runny viscosity. Horrible hand feel. 

    Will try to lower cost by playing with CAPB and Decyl Glucoside concentrations.   
  • BelassiBelassi Member
    I'm surprised.


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  • Cafe33Cafe33 Member
    edited July 15
    Revised formula, using Cocamide DEA to neutralize carbopol. Final pH 7.30-7.40

    In order of addition:

    2% Carbopol Aqua SF1
    40% dH20

    9% Decyl Glucoside
    3% Cocamide DEA
    15 % CAPB (30% active)

    0.15% EDTA 4 Na
    1.8% Polyquat 7
    0.10% BAC
    0.10 % Fragrance (Lemon grass EO)
    Trace color (unmeasured)

    Fairly expensive to manufacture (~1.10 USD per kg) but the product is good. Main aim was to use as little carbopol as possible. Would love to hear any comments or suggestions. 
  • BelassiBelassi Member
    dH20?
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  • Cafe33Cafe33 Member
    Distilled water. 40 % is the amount I used alongside the carbopol. The rest of the water was used to total 100% 
  • BelassiBelassi Member
    edited July 15
    Instead of using decyl glucoside, why not try using ALS, which will thicken with the CAPB, to avoid using SF1 as an (expensive) thickener? Also eliminating the need for the DEA. You'd need to leave the final pH <=6 of course. I don't like decyl glucoside anyway, it's short flow like SLES, draggy.
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  • Cafe33Cafe33 Member
    I am using Decyl Glucoside because it is non-ionic. I was under the impression that ALS is not compatible with benzalkonium chloride. Thats why I also left the pH closer to slightly alkaline for the benzalkonium. Is that an improper idea? 
  • Have you tried chlorphenesin?
    It is both antiseptic and sterilizing.

    INCI:chlorphenesin
    CAS: 104-29-0
    Molecular formula: C9H11ClO3
    Main component: 3-(4-chlorophenoxy)-1, 2-propanediol
    Suggested usage amount: 0.1-0.3%


  • @Cafe33

    Yes, using anionics with cationics is a no go. In this case it’s possible that it may render BAC much less effective or even ineffective as the affinity for biological membranes may be neutralized by the anionic.

    Are you going to be testing your formula for efficacy?

  • BelassiBelassi Member
    Damn, I had forgotten about that. What a nuisance.

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  • Cafe33Cafe33 Member
    letsalcido, yes I will be sending the soap for testing. I rushed into these formulations with BAC so I am not completely confident yet, I am still in the development stage. Will 0.10% BAC be a sufficient preservative for this system?  Is a pH of 7.40 sufficiently high ? 

    I am currently manufacturing spray sanitizers with a combination of BAC, Alcohol and EDTA 4Na as well as a multipurpose cleaner similar to concentrated Lysol. They will all be tested since we are aiming for compliance with the governing body here. 

    There are small villages where coronavirus has exploded, we are giving out bottles of our products as they hardly have anything to clean with. 

    Yes Belassi, I figure you had forgotten about that initial detail. 

    Also, I tried thickening further with 0.5% NaCl as suggested by the Lubrizol documentation - no result 
  • letsalcidoletsalcido Member
    edited July 16
    @Cafe33 I’m only familiar with the literature and mechanism of action, but not the most effective pH or whether it can be trusted as the only preservative as well (my assumption is yes, coupled with a high pH as with some antibacterial surface cleaners pH 9-10)

    NaCl won’t thicken Decyl Glucoside and CAPB, you’re missing an anionic (which we know can’t be in his formula). You can try HEC maybe paired with the carbopol aqua, or a PEG.



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