Future Kodachrome Colour Developing

Jason, the Kodachrome couplers were custom made for Kodak for the K14 process. The simplest cyan coupler is 4-Chloro-1-Napthol which I am sure is sold by Aldrich. It is by no means a Kodachrome coupler, but it forms a credible cyan dye. Some of the couplers are sold commercially and I think that someone has posted a source.

If you want more, I can start drawing structures, but I don't think it will help anyone but another Organic Chemist.

PE

If you want more, I can start drawing structures, but I don't think it will help anyone but another Organic Chemist.

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My point exactly!

I am not an organic chemist* and do not play one on TV.

Anyway, it might be interesting to get a bit of this coupler just to try as an experiment some day. Thanks for the info.


* or any other kind of chemist. There are days I'd like to change that. (Of course, there are many days that "would you like fries with that" sounds like a good line of work, too.)

The only reason I suggested the George Eastman House and possibly the National Archives/Library of Congress would be to help the poor fellow who has the shuttle launches on Kodachrome. I was not suggesting they could or even should/would do it on a commercial scale. My expertise is Gardening/Psychology, NOT organic chemistry. I don't own any Kodachrome, as I stated earlier, when that date got close, I gave away my rolls to someone else who claimed they would use it up in time.

Right now, I am shooting E-6 and sending it off for processing VIA Walmart ($6.88 USD/roll). My film of choice is Ektachrome that I am purchasing from a person on Ebay that specializes in selling old stocks. I have yet to run across a bad roll, she has been very good about selling good film rolls.

It's also possible he could talk to a chemistry graduate student at a local university. Just an idea.

GEH would not and could not do it even on a one-time basis! They are oriented in an entirely different direction than this.

And for those wishing to work with the Chloro Napthol, take precautions as this can be a nasty chemical in clumsy or let us say "inexperienced" hands.......

PE

madgardener said:

The only reason I suggested the George Eastman House and possibly the National Archives/Library of Congress would be to help the poor fellow who has the shuttle launches on Kodachrome. I was not suggesting they could or even should/would do it on a commercial scale. My expertise is Gardening/Psychology, NOT organic chemistry. I don't own any Kodachrome, as I stated earlier, when that date got close, I gave away my rolls to someone else who claimed they would use it up in time.

Right now, I am shooting E-6 and sending it off for processing VIA Walmart ($6.88 USD/roll). My film of choice is Ektachrome that I am purchasing from a person on Ebay that specializes in selling old stocks. I have yet to run across a bad roll, she has been very good about selling good film rolls.

It's also possible he could talk to a chemistry graduate student at a local university. Just an idea.

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Probably the same seller i have been buying it from!
My stock is shooting perfectly too been frozen for 7 years, unfortunately buying dead films is not going to keep E6 alive, ive got about 30 rolls in my freezer, i may buy another 20 from that seller.

Stephen Frizza said:

it will never be done commercially. Weather this be a K-14 processor like the K-lab or something custom built by proper engineers.

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I think Kelvin's K-Lab, (with whatever he has done with it) is the only hope left of processing kodachrome on a larger scale.
Dont know where any of the other remaining K-Labs are, but there may be others that come out of the woodwork.
Im not sure how easy it would be either to modify to run 16mm film through the machine. This would likely require different film sprockets, as far as im aware, the K-Labs only ran 35mm film through them.

I take it that the shuttle film was shot on 16mm?
If it was on 35mm, then that will make things much easier in a K-lab scenario anyway.

Photo Engineer said:

If you want more, I can start drawing structures, but I don't think it will help anyone but another Organic Chemist.

PE

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Ill be keen to see them, id add them to the Kodachrome Wiki if nothing else.
Who knows if any Organic Chemist reads this thread, but may be some use in the future if anyone goes down the track of K-14 processing.
May be useful to find the correct couplers for a K-lab machine, since the other simpler ones you mentioned may require different processing times for a K-lab.

The coupler names are in the patent for all to see. The only reason I would do anything is to show the actual structure, or one close to it. But then, if you search the name for the patent, or the Napthol I gave above, the structure is shown.

Such as here: http://www.sigmaaldrich.com/catalog/product/sigma/c8890?lang=en&region=US

PE

Has Stephen's exact process been documented here in this thread?

clayne said:

Has Stephen's exact process been documented here in this thread?

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No i dont think it has yet.

Ive created this page for the Cyan Coupler on the Kodachrome wiki.
Feel free to make any changes you feel are needed PE.
http://kodachromia.wikia.com/wiki/4-Chloro-1-naphthol

Great, but that isn't a K-14 coupler. It's just a simple cyan producing coupler. And, by the way, you see the price of that stuff, yes? Now, go get a price on the real thing!

On the other hand, for small quantities (say 100 rolls worth) you'd probably have to try to DIY it. So, just how DO you make 4-chloro-1-naphthol in your basement? Can it be done? Sure! But HOW is the (rhetorical) question!

It is encouraging to see all the interest in developing Kodachrome film. Of course this is a classic case of reinventing the wheel. People interested in the process should look at J.S. Friedman's "History of Color Photography" chapters 10 and 23. The book is available online for free at:

http://archive.org/stream/ost-art-h...h/historyofcolorph00frierich#page/n9/mode/2up


Friedman outlines the process and names a variety of color couplers which may be used for the complementary colors, cyan, magenta and yellow.


I think APUG should encourage someone with industry and interest to explore how to develop the batch amounts of Kodachrome which are still left unprocessed--including the shuttle launch materials. But I certainly don't suggest that this is anyone's responsibility or that pressure should be put on any individual or group to engineer such a method--that is contrary to the spirit of APUG. I'm simply suggesting that there is enough experience and talent out there to solve this problem.


Any non-standard process to develop Kodachrome will have problems. The substitute dye couplers and the dyes which they produce will probably lack saturation, stability and proper hue. Nonetheless they will reveal a color image which is otherwise lost and which might be preserved and corrected using other means; perhaps electronic. This seems a better solution than resorting to mere black and white development--all due respect to B&W photographers.


The process to develop Kodachrome is notoriously difficult. First the black layer, (the anti halation layer), must be removed by an alkaline wash using a scrub brush of some kind. Then the film must be developed in a black and white developer and stopped--BUT the stop bath must not be too acid as this destroys the sensitizing dyes which make the layers sensitive to blue, green and red light respectively. Then the red layer must be exposed to red light through the base of the film in a manner which exposes all of the undeveloped red sensitive grains--BUT NO OTHER GRAINS such as the ones in the blue and green layers. After red light exposure then develop in cyan developer and stop. The film now has cyan dye in it. Then expose the blue layer to blue light through the front of the film and develop with yellow developer and stop. The film now has cyan and yellow dyes in it. Next use a chemical to expose the green layer and make those grains develop-able; develop with a magenta developer and stop. Finally use Farmers Reducer or something like it--a BLIX-- to wash out the silver and leave only the dye images.


I only review this process because some people might not be aware of it and because I believe in returning to first principles. Kodak called the developing process K-14 because it had 14 steps to it. Complicated.


Nonetheless it is not impossible. It seems to me that a lot of people who are expert on processing cannot come forward because they are bound by non-disclosure agreements or similar concerns. This is to be expected and is perfectly proper. No inventory of the processing facilities has been revealed to my knowledge. There may be an unused batch of chemicals out there for all I know. When you come right down to it we are dealing with 1938 technology.


Time was when Kodak would go out of its way to help the consumer. George Eastman made his reputation by replacing all of the film plates he sold which were contaminated with bad gelatin. The cows from which the gelatin was made had eaten mustard plants and this material caused the photographic plates to fog. Eastman replaced the plates at no charge and hired chemists to get to the root of the problem. Bradford Washburn used Kodachrome to photograph Alaska when the sheet film first came out. But he was given tungsten film and did not use a filter to correct for daylight. Dr. Wesley Hanson worked out a process to correct for the wrong exposure in the lab and many of the images were saved. Can't we recover that helpful spirit? Just saying....

kb3lms said:

Great, but that isn't a K-14 coupler. It's just a simple cyan producing coupler. And, by the way, you see the price of that stuff, yes? Now, go get a price on the real thing!

On the other hand, for small quantities (say 100 rolls worth) you'd probably have to try to DIY it. So, just how DO you make 4-chloro-1-naphthol in your basement? Can it be done? Sure! But HOW is the (rhetorical) question!

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Yes it is very expensive, dont know how much would be required to process a roll, but cant be a huge amount of the chemical required for processing the film, or else the price of processing Kodachrome would have made it obsolete before Kodachrome even got off the ground!
Its also possible other chemical suppliers can supply it cheaper anyway.
I can only guess that the Kodak formulation of the coupler can be synthesised from 4-Chloro-1-naphthol as a building block?

Poisson Du Jour said:

Wwwwhat!? $250!?

:eek:
Come off the glue!

Other things you can do with an idle $250?
For me, a KEP-M gallery print, 81cm x61cm, dibonded, mounting battens and certificate, ready for the bright lights of the gallery. All that (including scan, colourimetrics, proofing etc) from film that remains available and abundant and is cheap to process. Kodachrome has gone. Tugging at the forelocks of a carcass is bizarre. Move on with what film you have and what is available.

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Wasn't the same thing said about Polaroid? I was surprised to see Polaroid come back, and would be astonished if Kodachrome could come back even as a niche product.. but since I was so wrong about the demise of Polaroid.. I'll wait and see on Kodachrome.

kb3lms said:

On the other hand, for small quantities (say 100 rolls worth) you'd probably have to try to DIY it. So, just how DO you make 4-chloro-1-naphthol in your basement? Can it be done? Sure! But HOW is the (rhetorical) question!

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May I take this opportunity to STRONGLY DISCOURAGE anyone reading this thread from attempting to synthesis any chemical compounds. Not only can it be very dangerous and potentially life threatening but it requires a firm knowledge of organic synthesis and a well equipped laboratory. Something that people do not usually have in their basement. Even a deceptively simple compound can be very difficult to make. As an example I give azulene which is a geometrical isomer of naphthalene a common and readily available chemical.

http://en.wikipedia.org/wiki/Pfau-Plattner_azulene_synthesis

constrast this with the naphthalene structure

http://en.wikipedia.org/wiki/Naphthalene

Instead of having two condensed six membered rings it has a five member and a seven member ring. On paper it would seem easy to move the center bond to accomplish this. A simple synthesis which assumes certain special raw materials also be available runs to a dozen steps.

The more this thread goes on the more it should become plain to everyone that Kodachrome processing is not coming back. There is no motivation or money to make it come back.

it requires a firm knowledge of organic synthesis and a well equipped laboratory. Something that people do not usually have in their basement.

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Exactly! You don't just go chemical shopping on eBay and mix up some stuff. This is not simple. Many folks here think emulsion making borders on the impossible yet K-14 has gone on for years! Basic emulsion making is a "walk in the park" compared to K-14.

As an example I give azulene which is a geometrical isomer of naphthalene. Instead of having two condensed six membered rings it has a five member and a seven member ring. On paper it would seem easy to move the center bond to accomplish this.

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How many of you understand what this means and how you would make it? I don't.

Now, if someone has the proper training, materials and equipment, I say go for it. All encouragement and the best of luck to you. It WOULD be great to see the remaining films developed in color.

If you don't know what you are doing this could all go wrong very quickly.

Kodachrome died off for a reason. Great as it was, and regarded by many as Kodak's flagship product, it WAS 1938 technology. There is just nothing more to see here. Move along.

Jerry, we worked with Guaiazulene quit a bit in our labs. It is a magenta dye that shifts to cyan in an acid condition. The problem was that we could not stabilize it.

Organic Chemistry by the untrained is a sure way to shorten your lifespan! I cannot believe this thread.

PE

Gerald C Koch said:

May I take this opportunity to STRONGLY DISCOURAGE anyone reading this thread from attempting to synthesis any chemical compounds. Not only can it be very dangerous and potentially life threatening but it requires a firm knowledge of organic synthesis and a well equipped laboratory. Something that people do not usually have in their basement. Even a deceptively simple compound can be very difficult to make. As an example I give azulene which is a geometrical isomer of naphthalene a common and readily available chemical.

http://en.wikipedia.org/wiki/Pfau-Plattner_azulene_synthesis

constrast this with the naphthalene structure

http://en.wikipedia.org/wiki/Naphthalene

Instead of having two condensed six membered rings it has a five member and a seven member ring. On paper it would seem easy to move the center bond to accomplish this. A simple synthesis which assumes certain special raw materials also be available runs to a dozen steps.

The more this thread goes on the more it should become plain to everyone that Kodachrome processing is not coming back. There is no motivation or money to make it come back.

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From reading this it sounds like we do have some Organic Chemists on this Forum!
lol
Anyway, as far as the saftey goes for the finished product, the K-14 chemicals are supposed to be no more dangerous than any other film processing chemicals such as C41, E6 etc, according to the MSDS that Kodak released for the K-14 chemicals.

Of course its potentially dangerous to synthesise chemicals etc with no chemistry experience, fume cabinets respirators etc.
I sure as hell wont be touching it, but im still interested to learn the chemical makeup for interests sake.

What an utterly fascinating battle of wills going on here...

:munch:

Ken

Many years ago the Dignan Newsletter published the formulas for all the K-12 and K-14 processing solutions.

Photo Engineer said:

Organic Chemistry by the untrained is a sure way to shorten your lifespan! I cannot believe this thread.

PE

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Neither can I. So far I have refrained from commenting on any of the Kodachrome threads that have run here over time mainly because I was never an avid Kodachrome user and therefore do not have the strong attachment to the product that many folk do have. I've also commented somewhere else that I have studied just enough chemistry to understand how much I do not know, particularly about organic synthesis.

It is surely time, as PE has suggested more than once, to close this thread. It is improbable that anyone is going to make Kodachrome processing chemicals in their basement lab or garden shed. The only way these chemicals could be made again is by someone with access to the expertise, money for facilities and therefore a strong commercial incentive. That incentive does not exist and will never exist again because the film is no longer being made.

Those who have an urgent need to process already exposed Kodachrome might be better advised to mount a world- wide search for unused Kodak chemicals - there must be some somewhere - and if they can be obtained then try to find a way to use them in a hand process similar to that which Stephen Frizza has done. Those that are sitting on unexposed Kodachrome in the hope of using it need to take a reality check and put it to it's only remaining use - as an item of history. OzJohn

Gerald C Koch said:

Many years ago the Dignan Newsletter published the formulas for all the K-12 and K-14 processing solutions.

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Dignan Photographic Report, 1975, Volume 3, p.91?

Could be wrong... Just askin'...



Ken

Unless everything has been documented process wise then the parties that be are only contributing to its final demise. Of course they're not making the film anymore and obviously very very few will even succeed. But to hold back information because "it's pointless" seems kind of anti-spirit here.

clayne said:

Unless everything has been documented process wise then the parties that be are only contributing to its final demise. Of course they're not making the film anymore and obviously very very few will even succeed. But to hold back information because "it's pointless" seems kind of anti-spirit here.

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I agree, as far as im concerned its history, and should be documented to preserve that.
Thats what i intend to do with the wiki, document the formulas and the process, no need to document how to synthesise any molecule.
The chemists can do that, if any are keen to go down that road, all they need to know is the composition of the molecules.

Forget worring about safety of APUG members, its quite obvious that no one here is going to be tampering with any dangerous chemicals, we are photographers, not chemists, those that may be qualified in chemistry will likely be familiar with all necessary precautions etc.....
The price for 2 grams of just the basic coupler would be enough to put most people off experimenting. Besides, im sure it would be possible to source the chemicals from china, they can pretty much reproduce any molecule over there, so let them play around!

Anyway, Steve Frizza made do using the basic couplers and they did the trick, so i wouldnt go overboard trying to get the exact formula, unless there was an attempt to run a K-lab machine, which i expect is designed to run at different specs for the K-14 chemistry.

Lets just forget about trying to process this film and turn our direction to documenting its history, let those who are dead set on processing it, make use of the information to help them on their "journey" if you can put it that way.

On the machine side of things, in the '70s I remember accompanying my father on trips around the countryside (Victoria, Aust) to install 'film processing machines'. We towed a tandem trailer with this beast on it in a wooden box. I don't know what process it was, but a bunch of guys in a backyard shed had cobbled these things together. It was pretty agricultural to look at. I think my father did the electronics as that was his hobby. My fondest memory was I used to hang around the workshop bending up scraps of plastic on a machine, amused me for hours So, it obviously wasn't a K-14 line, but several photolabs thought it was good enough to pay money for, so I guess I'm saying, mechanically, this sort of thing has been done before, just maybe not as extensive or complicated.

Nzoomed said:

Thats what i intend to do with the wiki, document the formulas and the process, no need to document how to synthesise any molecule.
The chemists can do that, if any are keen to go down that road, all they need to know is the composition of the molecules.

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I agree with this. There is no reason home amateurs start their own synthesis labs in their dark rooms. There may be professional synthesis labs, though, which can make these compounds for interested parties, expensive or not.

Nzoomed said:

The price for 2 grams of just the basic coupler would be enough to put most people off experimenting.

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If you mean 4-Chloro-1-naphthol, that's not overly expensive at Sigma Aldrich.

Nzoomed said:

Anyway, Steve Frizza made do using the basic couplers and they did the trick, so i wouldnt go overboard trying to get the exact formula

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Also remember that Steve Frizza runs a professional lab and tries to maintain very tight processing standards whenever he does something, just read his comments about Ilfochrome. In the case of Kodachrome, film will likely be aged by now and things won't turn out perfectly even in a properly dialed in K14 machine, if such a thing existed today. Chances are some Kodachrome owners are willing to relax a few expectations of perfection at this point in time, and in this case we have a good chance to get something going.

Ken Nadvornick said:

Dignan Photographic Report, 1975, Volume 3, p.91?

Could be wrong... Just askin'...



Ken

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IIRC the formulas appeared over several months as there was a lot to publish. The formulas and process times were all from Kodak's literature supplied to commercial processors.