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Thread: Schiff's bases

  1. #61

    Default Re: Schiff's bases

    Paul - just for comparison, your benzaldehyde base smells of almonds throughout the drydown? The indole thing loses its almond smell quite quickly..

  2. #62

    Default Re: Schiff's bases

    It is highly unlikely that you made a reaction product between Benzaldehyde and Indole Nizan, simply by mixing the two chemicals together and warming them. Indole is much less likely to react than Methyl Anthranilate. You probably have a mixture of Indole and Benzaldehyde which yo are smelling. Benzaldehyde is more volatile than Indole, and Indole is so much stronger (in my opinion), which is why the almond smell goes so quickly.

  3. #63

    Default Re: Schiff's bases

    I figured :\
    The only mystery now is why it became thick and red.. Could be that some of the
    residual acid in the benzaldehyde reacted? Or that just a small portion reacted?
    What a bummer..

  4. #64

    Default Re: Schiff's bases

    Are you sure you didn't just make a paste of the two chemicals? To make a Schiif's Base you need to mix Molar amounts of the two. So Indole has a molecular weight of 117.15 and Benzaldehyde has a weight of 106.12. So you are mixing 11.7 gms of Indole with 10.6 gms of Benzaldehyde; a lot of solid (Indole) to mix with the liquid (Benzaldehyde). Indole discolours very easily, and I'm not saying that you did not produce any Schiff''s Base, just that most of your two reagents remained unreacted.

  5. #65

    Default Re: Schiff's bases

    Yeah, I mixed then at 10:9.. Too bad it's diluted now.. I could have kept warming it
    to see if something happens..

  6. #66
    Paul Kiler
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    Default Re: Schiff's bases

    Quote Originally Posted by julian35 View Post
    Paul, absolutely brilliant Schiff's Base Compendium. Thank you for putting such a great document together and for making it available.

    (p.s. - Also wanted to mention I recently purchased a fantastic pair of Koure frames, I know you are someone that would appreciate that from a post I read somewhere.
    Paul's Headshot.jpg Oh Yes, Love my Koure Frames, Here's my headshot on the Red Carpet for the Taste Awards...
    And you are very welcome for the Compendium, I could not find any other similar resource for my own education, so I had to make it myself....
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  7. #67
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    Default Re: Schiff's bases

    Went back to the drawing board today. I'm sure I got a lot wrong last time and made too many assumptions.

    I'm wanting to make sure I do everything right this time so I have a few questions:

    1. How does one know when the reaction is DEFINITELY complete?
    2. Are schiff bases definitely supposed to be cloudy after they cool or is cloudiness an indication that the process is complete when they are still hot?

    I have four small samples brewing and I'm sure one of them isn't reacting at all, which is ok, it was an experiment and no, it isn't on Paul's compendium (Hexyl Cinnamic Aldehyde). The other three are definitely reacting because they've changed color and they have gotten thicker but not that much more thick than they were prior to heating, I've had them on the hot plate at 70C for over an hour now.

    Anisic Aldehyde/Methyl Anthranilate: Got a little yellow but not a lot
    Cinnamic Aldehyde/Methyl Anthranilate: Dark brown, almost black, can not see light through it in the vial
    C-11/Methyl Anthranilate: Turned a rich transparent orange/brown
    Hexyl Cinnamic Aldehyde/Methyl Anthranilate: No apparent change/reaction

    None of them are "very thick", just a bit more thick than before heating and none of them are cloudy... These reactions seem counter to what has been described (thick and cloudy).
    Last edited by JEBeasley; 8th February 2014 at 01:38 AM.
    Justin E. Beasley

  8. #68

    Default Re: Schiff's bases

    Quote Originally Posted by JEBeasley View Post
    Went back to the drawing board today. I'm sure I got a lot wrong last time and made too many assumptions.

    I'm wanting to make sure I do everything right this time so I have a few questions:

    1. How does one know when the reaction is DEFINITELY complete?
    2. Are schiff bases definitely supposed to be cloudy after they cool or is cloudiness an indication that the process is complete when they are still hot?

    I have four small samples brewing and I'm sure one of them isn't reacting at all, which is ok, it was an experiment and no, it isn't on Paul's compendium (Hexyl Cinnamic Aldehyde). The other three are definitely reacting because they've changed color and they have gotten thicker but not that much more thick than they were prior to heating, I've had them on the hot plate at 70C for over an hour now.

    Anisic Aldehyde/Methyl Anthranilate: Got a little yellow but not a lot
    Cinnamic Aldehyde/Methyl Anthranilate: Dark brown, almost black, can not see light through it in the vial
    C-11/Methyl Anthranilate: Turned a rich transparent orange/brown
    Hexyl Cinnamic Aldehyde/Methyl Anthranilate: No apparent change/reaction

    None of them are "very thick", just a bit more thick than before heating and none of them are cloudy... These reactions seem counter to what has been described (thick and cloudy).

    good questions Justin,

    i guess one is suppose to just mix stuff and guess....
    As this is a DIY forum to discuss Perfumery, I do not think that you comparing the size of your retort stands with each other is of much use. This Forum is not about Organic Chemistry or Chemical Synthesis, it is about Perfumery.

  9. #69

    Default Re: Schiff's bases

    How much are you making, Justin? Could it be that for small quantities and open vials, the water just evaporates in the process?

  10. #70
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    Default Re: Schiff's bases

    Quote Originally Posted by Nizan View Post
    How much are you making, Justin? Could it be that for small quantities and open vials, the water just evaporates in the process?
    They got thicker, the Cinnamic Aldehyde turned almost black and is thick as tar after it cooled. Everything else still flows albeit more like honey. I made three of them around 3.5g and one around .3g so they are small but only one I would consider truly micro. They never did get cloudy, it is possible that the water evaporated, there is a small amount of condensation around the upper 1/2 of the vials but it's a very fine mist. All said I had them on the hot plate for around two hours so I can't imagine the reaction never completed.

    I was curious if ketones would react so I made a micro sample of methyl cedryl ketone + methyl anthranilate too. Oddly it is quite a bit thicker, darker and smells less sweet and more pissy like cedar... I have no idea if this was a reaction or if it just condensed from the long cook time. The Hexyl Cinnamic Aldehyde got thicker and smells different too but once again I have no idea if it reacted. If the Hexyl Cinnamic Aldehyde actually did react then it was the slowest one to react with the least amount of visual change. This weekend I'm going to try a few others on Pauls compendium and not on his compendium (C12mna, C18, C14, Lyral, Helional). Ideally I'd like to have a small working sample of everything I can turn into a base, I figure "why not" more variety to work with and aldehydes are cheap and go bad quickly anyway.

    I've been analyzing Dzing! lately, it's one of my current favorites, it's such an even smelling perfume from start to finish that it got me thinking about how a perfume could be entirely comprised of dilute bases and more stable EOs. Even if it isn't made this way it seemed like an interesting concept to explore so I'm now hell bent on making as many bases as I can. Now if I just had a list of everything that can be made into a base, lol.
    Last edited by JEBeasley; 8th February 2014 at 07:05 AM.
    Justin E. Beasley

  11. #71
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    Default Re: Schiff's bases

    Quote Originally Posted by luigi_g View Post
    good questions Justin,

    i guess one is suppose to just mix stuff and guess....
    That's pretty much how I do most things, lol! Over all I'd say I'm pretty lucky to have all of my body parts and to be alive but I honestly don't know how to be any other way.
    Last edited by JEBeasley; 8th February 2014 at 07:18 AM.
    Justin E. Beasley

  12. #72
    Paul Kiler
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    Default Re: Schiff's bases

    Quote Originally Posted by Nizan View Post
    Paul - just for comparison, your benzaldehyde base smells of almonds throughout the drydown? The indole thing loses its almond smell quite quickly..
    Nizan, I'm not quite sure to what you refer, but if you are asking about whetehr I made ther Schiff base with these items, then no is the answer. The Compendium is simply a repository of research infromation, not my personal experience.

    Mr. JEBeasley , I can tell you that M.A. / Helional Schiff base is very close to a soild when at rest and room temp. So it's entirely possible that others could be in a similar state when cooled. But that's the only one I can recall that gets that way. But I'll bet it liquifies when warmer.

    PK
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  13. #73

    Default Re: Schiff's bases

    If your "Schiff's Base" is cloudy when cool, there is water present and so the reaction is not complete. By removing the water you drive the retain to completeness. I was never able to get Amyl Cinnamic Aldehyde or Hexyl Cinnamic Aldehyde to react with Methyl Anthranilate, to form Schiff's Bases. Heating at 70 deg C for several hours is too hot (I think), you will not produce a good quality. I have found that to rest a Ketone, takes much longer, if at all without using a vacuum to remove water. Despite what others think, I don't think it possible to make a Schiff's Base using Aldehyde C14 C16 or C18, for reasons given above. Of course you should all experiment as that is how we learn.

    So Paul, the Compendium of Schiff's Bases you provided are simply a list you have; you have not made any yourself?

  14. #74

    Default Re: Schiff's bases

    Nizan, I'm not quite sure to what you refer, but if you are asking about whetehr I made ther Schiff base with these items, then no is the answer. The Compendium is simply a repository of research infromation, not my personal experience.
    Ho, didn't realize that. I will report how the benzaldehyde went once I get my MA.

    By removing the water you drive the retain to completeness.
    David, do you mean that the presence of water somehow quenches the reaction?

  15. #75

    Default Re: Schiff's bases

    When mixing the aldehyde with Merthyl Anthranilate, you get the Schiff's Base plus water. This continues until an equilibrium is reached. To encourage the reaction to proceed in the direction you want it is necessary to remove the water.

  16. #76

    Default Re: Schiff's bases

    Quote Originally Posted by luigi_g View Post
    good questions Justin,

    i guess one is suppose to just mix stuff and guess....
    OOH, mee-ow!!

  17. #77
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    Default Re: Schiff's bases

    Quote Originally Posted by David Ruskin View Post
    If your "Schiff's Base" is cloudy when cool, there is water present and so the reaction is not complete. By removing the water you drive the retain to completeness. I was never able to get Amyl Cinnamic Aldehyde or Hexyl Cinnamic Aldehyde to react with Methyl Anthranilate, to form Schiff's Bases. Heating at 70 deg C for several hours is too hot (I think), you will not produce a good quality. I have found that to rest a Ketone, takes much longer, if at all without using a vacuum to remove water. Despite what others think, I don't think it possible to make a Schiff's Base using Aldehyde C14 C16 or C18, for reasons given above. Of course you should all experiment as that is how we learn.

    So Paul, the Compendium of Schiff's Bases you provided are simply a list you have; you have not made any yourself?
    If two hours @ 70C is too hot for too long then what are the correct times and temps or how can we find this out? When you say "not produce a good quality" does that mean it's oxidized by the heat or it's burnt or... What I made smells fine, the C11 base smells like an idealized **shudder** myrrh, without being sweet but it seems usable. I don't know though, I have yet to try to dilute them so maybe they are plasticized too much to be of use?
    Justin E. Beasley

  18. #78
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    Default Re: Schiff's bases

    I diluted my C11 schiff base sample today, I had to heat it with the solvent to get it all to dissolve. I only made a micro amount, enough to dilute and fill a 1 dram dropper bottle. The diluted sample is very cloudy like most of the absolutes I dilute. I probably won't filter this one because it's such a small amount that I would lose half of it but I will try to dilute and "dry" a couple others as soon as I can find my nitrile gloves. Since all of my absolutes are cloudy I might just wait and filter and dry the whole perfume, if it even get's to that stage.

    This C-11 is interesting, it's a musty, dry, grapey, powdery version of myrrh, I can see it being very useful in incense accords with frankincense. Even if it's over-cooked I still like it.
    Justin E. Beasley

  19. #79
    Paul Kiler
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    Default Re: Schiff's bases

    Quote Originally Posted by David Ruskin View Post
    So Paul, the Compendium of Schiff's Bases you provided are simply a list you have; you have not made any yourself?
    For me the Compendium was about knowing more what something was supposed to smell like, as gathered from sources. There was/is hope to make some of them, but it was a place to put and cross reference the information, that I'd not seen before in one spot.. It is a comparative analysis paper. And now we all have a stepping stone to embark from, don't we...? It was also prompted by working with the Perfume Chemist friend I have who wanted to make some for me. So it was more about finding things that sounded interesting, and then to have others do the work for me to order so that I could get that material. Sort of delegating the tasks so I can use my skills elsewhere.

    This Perfume Chemist friend talked about making all kinds of cool things he knows about, cool aldehydes not currently Produced, Schiff Bases not currently produced, Rum Absolute... Etc...

    I'm sure he'll come into play when we get Perfumer Spupply House up and in swing, making things for us that no one else will be able to sell.

    I have made one schiff's base, Cuminaldehyde and MA, which didn't change much from Cuminaldehdye...

    So, That's where it all stands presently...

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  20. #80

    Default Re: Schiff's bases

    Quote Originally Posted by JEBeasley View Post
    If two hours @ 70C is too hot for too long then what are the correct times and temps or how can we find this out? When you say "not produce a good quality" does that mean it's oxidized by the heat or it's burnt or... What I made smells fine, the C11 base smells like an idealized **shudder** myrrh, without being sweet but it seems usable. I don't know though, I have yet to try to dilute them so maybe they are plasticized too much to be of use?
    The one article I read describing the synthesis of a Schiff's Base using Methyl ANthranilate, said the temperature should be no higher than 50 deg C. If your sample, cooked at 70 deg smells fine, then it is OK, and I was wrong. I thought that at 70 deg there would be danger of burning. Justin, why do you think your Absolutes go cloudy when diluted? Are you diluting into alcohol that contains too much water? Anyway, I'm glad you like what you have done with Aldehyde C11. You should try making a Base with Aldehyde C12 MNA; one that I particularly like.

  21. #81
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    Default Re: Schiff's bases

    I don't know why my absolutes might be cloudy... Are they of poor quality? Perhaps I don't heat them enough so that they dissolve? I use 95%+ cane alcohol from Alchemical Solutions.
    http://organicalcohol.com/store/inde...cohol-1-gallon
    Is this a bad sign? If I make a blend from mostly EO's or all EO's it will be cloudy every single time, without exception. If I let the blend sit undisturbed for a couple of days it will clear up but as soon as I agitate it gets cloudy again. I assumed it was a small amount of naturally occurring water in the absolutes. Do resellers add water in order to add weight to absolutes? It could also be due to temps in my work room, I keep it pretty cold in there since I have no heater register in that back room.
    Last edited by JEBeasley; 9th February 2014 at 08:50 AM.
    Justin E. Beasley

  22. #82

    Default Re: Schiff's bases

    Justin - this hasn't happened to me often. At what concentrations are you getting the cloudiness?

  23. #83

    Default Re: Schiff's bases

    By the very definition of an Absolute I would have thought they would be soluble in Absolute Alcohol. That is the way an Absolute is prepared. Seems to me that there is something in your Absolutes or your alcohol that is not soluble. The common material here is the alcohol.

  24. #84
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    Default Re: Schiff's bases

    Quote Originally Posted by Nizan View Post
    Justin - this hasn't happened to me often. At what concentrations are you getting the cloudiness?
    I dilute all of my absolutes @ 10%. I just thought of something... the alcohol I have been using (cane) is NOT ideal because it has such a strong malty odor so I dilute everything with 40% DPG and 60% alcohol to keep the malt and alcohol to a minimum, sometimes it overpowers the smell of the material it is diluting. So, it's probably the DPG... Sorry, I forgot about that. I was concerned for a minute but I went in there and looked at them all and thought about my dilution process.

    Out of the 14 absolutes I currently have diluted six are very cloudy, with some larger sediment, so that I can not see the dropper inside and three are half cloudy, the rest are clear with sediment floating around on the bottom or a thin layer that doesn't stay diluted.
    Justin E. Beasley

  25. #85

    Default Re: Schiff's bases

    Have you tried mixing your DPG with your alcohol, to see what happens? Also, have you tried diluting an Absolute with only your DPG, to see what happens? And finally, have you tried just using your alcohol with your absolutes? As far as I am aware DPG should cause no problems with most Absolutes (not all, but most).

    If your alcohol smells strongly, of anything, it is not suitable for Perfumery.

  26. #86
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    Default Re: Schiff's bases

    Quote Originally Posted by David Ruskin View Post
    Have you tried mixing your DPG with your alcohol, to see what happens? Also, have you tried diluting an Absolute with only your DPG, to see what happens? And finally, have you tried just using your alcohol with your absolutes? As far as I am aware DPG should cause no problems with most Absolutes (not all, but most).
    If your alcohol smells strongly, of anything, it is not suitable for Perfumery.
    I dilute all of my AC's with the same DPG + Alc mixture and ratio, I only get clouding with a couple AC's that probably aren't solvent in DPG (I'll have to look them up). The DPG + Alc combo does not cloud by itself, only when combined with other materials.

    When I purchased the Ethyl Alcohol I was not aware that the three different types available by that company would be so different, after all 95% alc is 95% alcohol and 5% water right? Well, as it turned out, I got the alc home and it smelled more malty than the perfumers alc I purchased from creating perfume. I made a couple dilutions @ 10% and realized that I couldn't smell the material over the alcohol because the alcohol smell and maltiness were too strong so I cut my dilutions with 40% DPG and THEN I was able to smell the material from the bottle...

    Since I've joined this board I have spoken with another member who had exactly the same issue with the same alcohol from the same place, this was in a thread before the board change. I planned on finishing off the gallon of cane alc I have and then go for denatured from Remet or something. After those initial dilutions, which smelled overly malty and alcoholic, I never diluted with plain alcohol again and didn't look back until now. It looks as though by trying to solve one problem I created another, bleh.

    I have not tried DPG only + absolutes
    I have not tried Alc only + absolutes

    I will experiment with my absolutes and DPG/Alc soon to see if I can isolate the problem. It will take a couple of days to get this hammered out as I have a lot on my plate right now but I'll report back when I do.

    In retrospect, it is also possible that the schiff base I made is not entirely soluble in DPG and thus is cloudy as a result of using 40% DPG in the dilution, I will only know by creating another sample and diluting it with alcohol only. Bottom line is I need new alcohol in order to help root out some of these issues. I'll look through the alcohol threads and see which one Paul buys from Remet, hopefully that will be suitable for absolute dilution - does anyone know? Should I be diluting all materials with pure grain alcohol and using the denatured blend for the final perfume dilution? Grape alcohol only or will grain alcohol do? Supposedly grape has the least smell but it's twice the cost.

    Thanks for your help.
    Last edited by JEBeasley; 9th February 2014 at 09:02 PM.
    Justin E. Beasley

  27. #87

    Default Re: Schiff's bases

    If the Absolue dont dissolve in Alcohol, reduce the concentration and or try warm up a bit (to max 40 celsius)
    Depending on your room temperature, this can work.

  28. #88

    Default Re: Schiff's bases

    I have question about producing Shiff bases. I made some MA / Citral yesterday after reading here,
    but it didnt come red color as usual. Ok i didnt heat that much al usual. It remain yellow. (60 degrees at 30 minutes).

    Im looking for solution to catalyse the process without heat them to much, because aldehydes are sensitive
    to temperature. Can vacuum do the job? I mean by reducing atomspheric pression, they sould react better in theory.

    What you think about?

    Another thing, some Shiff base dont change much color at heating process, but become darker next day after some hours at room temp.
    Last edited by bigbang; 10th February 2014 at 08:48 AM.

  29. #89

    Default Re: Schiff's bases

    Quote Originally Posted by JEBeasley View Post
    I dilute all of my AC's with the same DPG + Alc mixture and ratio, I only get clouding with a couple AC's that probably aren't solvent in DPG (I'll have to look them up). The DPG + Alc combo does not cloud by itself, only when combined with other materials.

    When I purchased the Ethyl Alcohol I was not aware that the three different types available by that company would be so different, after all 95% alc is 95% alcohol and 5% water right? Well, as it turned out, I got the alc home and it smelled more malty than the perfumers alc I purchased from creating perfume. I made a couple dilutions @ 10% and realized that I couldn't smell the material over the alcohol because the alcohol smell and maltiness were too strong so I cut my dilutions with 40% DPG and THEN I was able to smell the material from the bottle...

    Since I've joined this board I have spoken with another member who had exactly the same issue with the same alcohol from the same place, this was in a thread before the board change. I planned on finishing off the gallon of cane alc I have and then go for denatured from Remet or something. After those initial dilutions, which smelled overly malty and alcoholic, I never diluted with plain alcohol again and didn't look back until now. It looks as though by trying to solve one problem I created another, bleh.

    I have not tried DPG only + absolutes
    I have not tried Alc only + absolutes

    I will experiment with my absolutes and DPG/Alc soon to see if I can isolate the problem. It will take a couple of days to get this hammered out as I have a lot on my plate right now but I'll report back when I do.

    In retrospect, it is also possible that the schiff base I made is not entirely soluble in DPG and thus is cloudy as a result of using 40% DPG in the dilution, I will only know by creating another sample and diluting it with alcohol only. Bottom line is I need new alcohol in order to help root out some of these issues. I'll look through the alcohol threads and see which one Paul buys from Remet, hopefully that will be suitable for absolute dilution - does anyone know? Should I be diluting all materials with pure grain alcohol and using the denatured blend for the final perfume dilution? Grape alcohol only or will grain alcohol do? Supposedly grape has the least smell but it's twice the cost.

    Thanks for your help.
    When I was working, the only time we used alcohol was to dilute our finished fragrances. Alcohol was never used as a solvent to dilute individual ingredients. Other, more suitable solvents were always used. So if the end product was going to be water based (such as Shampoo, Shower Gel, Hard Surface Cleaner etc. ) or if it was a fine fragrance, the solvent we used was DPG. If the end product was oil based (such as massage oil, candle, body cream etc.) a more suitable solvent was used. From memory we never had very few Absolutes that did not dissolve in DPG, although for some we used either Benzyl Benzoate or Benzyl Alcohol.

    I still maintain that if your Schiff Base is cloudy, there is water present.

  30. #90

    Default Re: Schiff's bases

    Quote Originally Posted by bigbang View Post
    I have question about producing Shiff bases. I made some MA / Citral yesterday after reading here,
    but it didnt come red color as usual. Ok i didnt heat that much al usual. It remain yellow. (60 degrees at 30 minutes).

    Im looking for solution to catalyse the process without heat them to much, because aldehydes are sensitive
    to temperature. Can vacuum do the job? I mean by reducing atomspheric pression, they sould react better in theory.

    What you think about?

    Another thing, some Shiff base dont change much color at heating process, but become darker next day after some hours at room temp.
    To encourage the reaction, it is a good idea to remove the water that is being formed. A vacuum should help to do this.

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