Caffeic Acid-fill of beans

Alan Johnson · Jul 22, 2014

Caffeic acid is often mentioned as the possible developing agent in the instant coffee based developer Caffenol:
http://caffenol.blogspot.de/2010/03/caffenol-c-m-recipe.html
I compared the activity of Caffenol-C-M with that of a similar solution in which the 40g/L instant coffee (Lidl Arabica) was replaced by 4g/L caffeic acid (axenic.us).

With the caffeic acid developer even increasing the development time by 40% compared with that for Caffenol-C-M did not give a density as high as was obtained with Caffenol-C-M.

Roasting coffee beans does give caffeic acid:
http://coffeechemistry.com/acids/chlorogenic-acid.html
However in my experiment there was not a simple match in activity between instant coffee and the supplied caffeic acid.
Coffee seems to be better.

aRolleiBrujo · Jul 22, 2014

Alan Johnson said:
Caffeic acid is often mentioned as the possible developing agent in the instant coffee based developer Caffenol:
http://caffenol.blogspot.de/2010/03/caffenol-c-m-recipe.html
I compared the activity of Caffenol-C-M with that of a similar solution in which the 40g/L instant coffee (Lidl Arabica) was replaced by 4g/L caffeic acid (axenic.us).

With the caffeic acid developer even increasing the development time by 40% compared with that for Caffenol-C-M did not give a density as high as was obtained with Caffenol-C-M.

Roasting coffee beans does give caffeic acid:
http://coffeechemistry.com/acids/chlorogenic-acid.html
However in my experiment there was not a simple match in activity between instant coffee and the supplied caffeic acid.
Coffee seems to be better.

wow!

removed account4 · Jul 22, 2014

hi alan

ive never used straight caffic acid, never found a need since instant oe npbeans are so cheap.
thanks for the experiment though.
i am a bit confused though, you used arabica instant coffee rather than cheap cheap instant ?

while it worked with your arabica instant , have you done it with the cheapest of the cheap instant
which is mistly robusta and very little arabica ?

i use 100%. robusta beans. and it works like a charm.

have fun
john

ps. what recipe did you use with the straight liquid caffic acid, the same cm substituting the
solution for the coffee? or something different ? even different cheap instants have different amounts of caffic acid ..

Alan Johnson · Jul 22, 2014

Hi John,
I used Arabica instant because that is what I drink. IDK which is the best type for Caffenol.
My caffeic acid recipe was Reinhold's Caffenol-C-M with the 40g/L instant coffee omitted and replaced by 4g/L caffeic acid.
I thought Reinhold's formula produces very nice negatives, it seems to have a good reputation among Caffenol users.
btw, caffeic acid is an off-white powder.

removed account4 · Jul 22, 2014

hi alan

you might ger better results, even from the instant
by using non arabica beans ...
i am sure you instant had some in it ( even though the label said arabica )
because it wouldnt have worked otherwise

i guess theres other magical stuff going on with caffenol other than
the caffic acid
.you might pm / contact reinhold and tell him your findings,
i am sure hed be interested

have fun caffenolling !
john

aRolleiBrujo · Jul 22, 2014

jnanian said:
hi alan

you might ger better results, even from the instant
by using non arabica beans ...
i am sure you instant had some in it ( even though the label said arabica )
because it wouldnt have worked otherwise

i guess theres other magical stuff going on with caffenol other than
the caffic acid
.you might pm / contact reinhold and tell him your findings,
i am sure hed be interested

have fun caffenolling !
john

I'm on my way there as well! I can't wait!

Rudeofus · Jul 22, 2014

Caffeic Acid, the compound suggested to be the main developing agent, looks a lot like Catechol, and like HQ it will likely exhibit a large induction period. Note, that e.g. Pyrocat HD uses Phenidone as primary developer.

There are at least three possible reasons why coffee worked better/faster in your experiment than Caffeic Acid alone:

Some component in coffee may act super additively with Caffeic Acid. I have no idea which one that could be, but there are supposedly over 1.000 distinct chemical compounds in coffee.
There may be stronger development compounds present, like Hydroxyhydroquinone.
Some component in coffee could act as wetting agent, which has a similar effect as a primary developer. I have seen patents (e.g. US5962202) about quaternary amines doing this, and sure enough, there is some compound like that to be found in coffee: Trigonelline.

aRolleiBrujo · Jul 22, 2014

Rudeofus said:
Caffeic Acid, the compound suggested to be the main developing agent, looks a lot like Catechol, and like HQ it will likely exhibit a large induction period. Note, that e.g. Pyrocat HD uses Phenidone as primary developer.

There are at least three possible reasons why coffee worked better/faster in your experiment than Caffeic Acid alone:

Some component in coffee may act super additively with Caffeic Acid. I have no idea which one that could be, but there are supposedly over 1.000 distinct chemical compounds in coffee.

There may be stronger development compounds present, like Hydroxyhydroquinone.

Some component in coffee could act as wetting agent, which has a similar effect as a primary developer. I have seen patents (e.g. US5962202) about quaternary amines doing this, and sure enough, there is some compound like that to be found in coffee: Trigonelline.

Way to edgy for me mate, just for curiosity sake, which substance shall I use? ty!

NedL · Jul 22, 2014

But the interesting thing here is that it seems to show that caffeic acid might not be the whole story. I remember reading that roasted coffee contains something like 300 different volatile compounds and 300 non-volatile soluble compounds. I'd guess instant coffee might have fewer, but I don't know.

Edit: I think Rudeofus covered it!

removed account4 · Jul 22, 2014

ned

instant coffe is made from roasted coffee ..
it has been roasted, ground and brewed ..
and then chilled and DEmoisturized/ DEhydrated
( freeze dried as they say )
the result is granules that re- dissolve into water
without the need of the coffee making ritual.

if you google how they make instant coffee there
is probably a video on the tube or a coffee company's website ...

removed account4 · Jul 22, 2014

the link speaks about Trigonelline ...
but some of those things in the article that also contain Trigonelline
have been used/attempted to use as a film developer ( i think darkroomexperimente did those ingredients in his/ her qwest to develop )
and they failed ... besides it says it is in arabica coffee,
and arabica coffee fails as a developer, for coffee to develop
film it has to be robusta coffee, there is a difference between the two varieties.
and one of he biggest stumbling blocks fiest time caffenol users have
is using the wrong kind ( arabica ) beans...

alan said he used arabica instant, but chances are that it was a blend of arabica and robusta
wih a higher content of arabica sp they called it arabica .. like the 7-11 near me sells KONA blend it might have a little kona in there
but it is mostly something else since it is 77cents a 58 oz cup
and kona costs about 100$ a lb. ( or did when my work sold it ), and it processed his film so it had robusta in it .. just like " espresso coffee"
( not espresso roast which describes the roast ) espresso often times contains
robusta beans so the shot has seed (bottom) body (the shot) and krema (foam)
pure arabica often times does not have krema after pressured-boiled-water
is pumped through it ...

NedL · Jul 22, 2014

John, I was thinking of all those volatile parts... not sure they'd make it through the freeze-drying process. This morning I drank Sumatra Lintong Toba Batak, and some Costa Rica Magdalena Vega. I roasted both on Monday. The Costa Rica will reach peak flavor tomorrow, still be wonderful on Thursday, and then it will go downhill very quickly. The Sumatra will be perfect on Thursday and still good on Friday, but then start to slowly get stale. The flavors change so much just from one day to the next....

I'll skip the freeze dried robusta unless it's for developer!

removed account4 · Jul 22, 2014

NedL said:
John, I was thinking of all those volatile parts... not sure they'd make it through the freeze-drying process. This morning I drank Sumatra Lintong Toba Batak, and some Costa Rica Magdalena Vega. I roasted both on Monday. The Costa Rica will reach peak flavor tomorrow, still be wonderful on Thursday, and then it will go downhill very quickly. The Sumatra will be perfect on Thursday and still good on Friday, but then start to slowly get stale. The flavors change so much just from one day to the next....

I'll skip the freeze dried robusta unless it's for developer!

yum!

have a cup for me

Rudeofus · Jul 23, 2014

jnanian said:
the link speaks about Trigonelline ...
but some of those things in the article that also contain Trigonelline
have been used/attempted to use as a film developer ( i think darkroomexperimente did those ingredients in his/ her qwest to develop )
and they failed ... besides it says it is in arabica coffee,
and arabica coffee fails as a developer, for coffee to develop

There are nice and informative articles about the chemistry of coffee to be found here, here and here. The first article states that Arabica and Robusto have 1% and 0.7% of this compound. If you look at the patent I mentioned before, you should not expect developing action from Trigonelline alone, but much increased development action if both Trigonelline and a secondary development agent are present.

Note, that this is all theory. We have no idea whether Trigonelline is really the key to higher dev action, unless someone makes an experiment with Trigonelline, Caffeic Acid and Ascorbic Acid. Since Trigonelline is not exactly a cheap compound either, so I don't expect anyone to make that test any time soon.

removed account4 · Jul 23, 2014

isolated compounds, experiments &c seems like a lot of work Rudeofus
i'll just stick to my home roasted robusto sumatran beans ... i seem to have a lifetime supply
no theories, no isolation, no expensive compounds no worries ...
just throw a handful of beans in my wok, turn on the heat, roast the beans, grind them, make coffee, add
vit c, and washing soda, add film, wash, fix, presto, negatives ...

as i wrote in my caffenol cookbook entry, i am not one of the kings of caffenol, i don't measure perfectly,
( if at all ) i don't have fancy names for what i make &c.

when its all said and done, its just coffee, and it is cheap as dirt ( and it works great ! )

Rudeofus · Jul 23, 2014

John, you are 100% correct, and I don't expect anyone to use purified compounds for US$100+ instead of roast coffee, with questionable result at best.

The whole situation does remind me of the gelatin situation several decades ago. Certain impurities in the gelatin gave photographic emulsions much higher light sensitivity and developability than the same silver halide crystals would have without gelatin. Instead of saying "well, why not just use it if it works", photographic researchers set out to investigate the matter in great detail, discovering sensitization techniques that give us fine grained ISO 400, and very workable ISO 1200 film.

While I don't expect similar break through results with coffee developer research (use Xtol, TMAX or DD-X if you want a good balance of grain, speed and sharpness), knowing how and why roast coffee develops film the way it does might at least give us better recipes.

Alan Johnson · Jul 23, 2014

I repeated a test, to see if the result is reproducible.
I measured the weight of my instant coffee needed to make a 200ml cup of coffee to drink, =1.6 grams.
200 ml contains up to 0.175g caffeic acid, see section on chlorogenic acids:
http://www.internationalcoffeetraders.ca/page4.html
Hence the 40g/L instant coffee in Caffenol-C-M contains up to (40/1.6) x 0.175 =4.3 g caffeic acid.

I repeated my previous test in which 4g/L caffeic acid was used in place of 40g/L instant coffee.
The result was exactly the same as before, developing in the caffeic acid brew for 40% longer than used for Caffenol-C-M does not give as high a density as Caffenol-C-M.
This seems to verify that caffeic acid is not responsible for all the development with Caffenol-C-M.

removed account4 · Jul 23, 2014

thanks for repeating the test alan.
maybe the problem is the caffic acid isn't "photo-grade"

Alan Johnson · Jul 23, 2014

My caffeic acid does not provide a claim for purity on the pack.
I used an amount which was close to the maximum estimate for its content in instant coffee.
Except in the rather unlikely case that it contains some kind of developer restrainer the purity appears not to be that important.

removed account4 · Jul 23, 2014

Alan Johnson said:
My caffeic acid does not provide a claim for purity on the pack.
I used an amount which was close to the maximum estimate for its content in instant coffee.
Except in the rather unlikely case that it contains some kind of developer restrainer the purity appears not to be that important.

sorry to ask a silly question, but i am clueless in these matters ...
how do you know the amount of caffic acid that was in your instant coffee ?
different coffees have different amounts ...
it varies wildly ( by some reports ) between varieties of beans ...
and instant coffees are never the same from batch to batch and brand to brand ...

Alan Johnson · Jul 23, 2014

John,
Best I could do was to calculate the likely maximum amount of caffeic acid in Caffenol-C-M as given in the link in post 17 and make sure to use this amount for the test using caffeic acid in place of coffee.
The caffeic acid content of a 200ml cup of coffee is given as 35-175 mg.I weighed the amount of coffee I would use to make this size cup,=1.6 grams,so this contains a maximum of 0.175g caffeic acid.Then I multiplied by 40/1.6 to calculate the maximum amount of caffeic acid in 1L of Caffenol-C-M. This came to 4.3g.
Since I used 4g in my brew made from caffeic acid it is unlikely that there was any error in my test due to using too little caffeic acid.

removed account4 · Jul 23, 2014

huh ...
that's really interesting because as you know
the caffenol gurus suggest it is caffic acid that does the development ..
and they suggest robusta because it has caffic acid and arabica doesn't..

thanks again ..

totally stumped.
john

aRolleiBrujo · Jul 23, 2014

Can anyone help me find the "right" fixer for caffenol? I dont know what to look for! ty

Alan Johnson · Jul 23, 2014

Probably not true that Caffenol requires a special fixer.The fixer just has to dissolve residual silver bromide as it would have to with any other developer.However, there could be a problem with the very high sodium carbonate alkali concentration in Caffenol resulting in the acid stop bath and acid fixer getting neutralized and failing.IMO a good way to prevent this is to give the film a quick rinse with water after the Caffenol development and before the stop bath.

aRolleiBrujo · Jul 23, 2014

Alan Johnson said:
Probably not true that Caffenol requires a special fixer.The fixer just has to dissolve residual silver bromide as it would have to with any other developer.However, there could be a problem with the very high sodium carbonate alkali concentration in Caffenol resulting in the acid stop bath and acid fixer getting neutralized and failing.IMO a good way to prevent this is to give the film a quick rinse with water after the Caffenol development and before the stop bath.

Alan, Please pardon, my ignorance, it is just that I am very new to the film and the devolping at home world, that I have no idea which fixer to consider, nor, do I even know what it is, save for a few online tutorials!

Caffeic Acid-fill of beans

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