Kodachrome

[piratelogy]

I would shoot 120 K14 no problem.

Maybe you should codify your process and give it a name, like KN-1 or something

EDIT: So can I start buying old K14 rolls on ePay now please please? (On a side note, most of the expired KC 64 on eBay seems to be from the 80's and 90's. Would I just use the usual one stop per decade rule?)

I have been, and it seems to work decently like that. I've found it seems to make decent slides up to 3 stops over(It starts to lose colors after that but still has images) so I'd air on the side of overexposure rather than under.

 

[flavio81]

I've posted the entire K12 set here on APUG. I would have to look it up again.

Did not find it but found useful information given by you and others here:
(there was a url link here which no longer exists)

Also, for the interested, see here, where I collect some of PE's posts on Kodachrome so he does not need to repeat again all over:
(there was a url link here which no longer exists)

 

[flavio81]

Maybe you should codify your process and give it a name, like KN-1 or something

"Pirate-K14"
"Ersatz-K14"
"K13 process"
"Cheapo-14 process"

 

[keenmaster486]

Look at this quote from Dead Link Removed:

"Never more, alas. Unless, of course, some chemist some day comes up with a way to replicate the complex, expensive developing process. Until then, McCurry is biding his time. 'I have a few rolls of Kodachrome in the fridge,' he claims. 'I’m just going to leave it there. My fridge would be kind of empty without them. If they ever revive Kodachrome like they did Polaroid, I’ll be poised and ready to go!'"​

If this project gets off the ground, don't y'all think we should try to contact McCurry and see if he's game?


Also, what about speeds other than 64? Kodachrome 25? I suppose you'd have to change the development time?

 

[flavio81]

If this project gets off the ground, don't y'all think we should try to contact McCurry and see if he's game?

We can make a deal with him:

"We give you the complete K14 recipe, if you give us the complete curry recipe."

We can try to contact Ronald McDonald for a similar deal. After all, he likes bold colors(red, yellow), and also holds a special recipe.

 

[piratelogy]

I have been, and it seems to work decently like that. I've found it seems to make decent slides up to 3 stops over(It starts to lose colors after that but still has images) so I'd air on the side of overexposure rather than under.

Look at this quote from Dead Link Removed:

"Never more, alas. Unless, of course, some chemist some day comes up with a way to replicate the complex, expensive developing process. Until then, McCurry is biding his time. 'I have a few rolls of Kodachrome in the fridge,' he claims. 'I’m just going to leave it there. My fridge would be kind of empty without them. If they ever revive Kodachrome like they did Polaroid, I’ll be poised and ready to go!'"​

If this project gets off the ground, don't y'all think we should try to contact McCurry and see if he's game?


Also, what about speeds other than 64? Kodachrome 25? I suppose you'd have to change the development time?

I've done a few rolls of K25, worked the same. I've done far more K64 rolls, mostly because I wanted to stay with the same emulsion until I was getting consistent chemistry results.

Honestly, I think I'd be terrified to develop a roll of McCurry's film. Thats a lot of pressure for my little lab

 

[Theo Sulphate]

I can't yet deal with the lengths required for cine film, I'm stretching myself to evenly re-expose a 36exp roll as the re-exposures are all by hand. I am however working on it. I have a couple rolls of double-8mm and 16mm Kodachrome that I'm trying to find a way to process properly.

Understood. If it becomes possible, let me know. Thank you.

Also thank you for describing your work so far.

 

[falotico]

Sorry about posting the wrong coupler for yellow. Here is the set published in the standard text:

Principles of Color Photography, Evans, Hanson, Brewer, edition 1953 on page 261 lists the following dye couplers as suitable for Kodachrome:

cyan
2,4-dichloro-1-naphthol

magenta
p-nitrobenzyl-cyanide

yellow
naphthoylacetanilide

Text talks of p-phenylenediamine developers.

Later on better couplers--presumably more stable--were used. This whole Kodachrome effort is basically an effort at re-inventing the wheel. Except that nobody seems to listen to what the experts on the wheel are telling them. I don't think we'll get anywhere until somebody talks about synthesizing couplers in a private lab. In other words, if you want to get serious you will have to study organic chemistry.

 

[piratelogy]

Sorry about posting the wrong coupler for yellow. Here is the set published in the standard text:

Principles of Color Photography, Evans, Hanson, Brewer, edition 1953 on page 261 lists the following dye couplers as suitable for Kodachrome:

cyan
2,4-dichloro-1-naphthol

magenta
p-nitrobenzyl-cyanide

yellow
naphthoylacetanilide

Text talks of p-phenylenediamine developers.

Later on better couplers--presumably more stable--were used. This whole Kodachrome effort is basically an effort at re-inventing the wheel. Except that nobody seems to listen to what the experts on the wheel are telling them. I don't think we'll get anywhere until somebody talks about synthesizing couplers in a private lab. In other words, if you want to get serious you will have to study organic chemistry.

Except that I'm getting results without synthesizing couplers in a lab or having any background in organic chemistry. I'd say I'm getting somewhere.... Will it be perfectly stable and kodachrome identical? Probably not. But I'm well into the "acceptable results" category.

 

[flavio81]

Except that nobody seems to listen to what the experts on the wheel are telling them. I don't think we'll get anywhere until somebody talks about synthesizing couplers in a private lab. In other words, if you want to get serious you will have to study organic chemistry.

... Or you can get serious by sourcing the chemicals from SA, other companies, or other color products.

Just as an example:

2,4-dichloro-1-naphthol
http://www.sigmaaldrich.com/catalog/product/aldrich/251976?lang=en&region=PE

Except that I'm getting results without synthesizing couplers in a lab or having any background in organic chemistry. I'd say I'm getting somewhere.... Will it be perfectly stable and kodachrome identical? Probably not. But I'm well into the "acceptable results" category.

MORE POWER TO YOU my friend!

Remember that "perfect" is the enemy of "good enough"!

 

[keenmaster486]

Amen brother.

 

[Photo Engineer]

Try reading the patent gentlemen!

PE

 

[fstop]

Try reading the patent gentlemen!

PE

That's too easy

 

[Sirius Glass]

Try reading the patent gentlemen!

PE

Next you will be posting RTFM!!

 

[viridari]

If Kodak relaunch Kodachrome and one development center for Kodachrome; how many rolls you will buy????

Depends on if it's just 135 or if we'll also get 120.

If we get 120, I might go broke.

 

[falotico]

KODACHROME DYE COUPLERS FROM US PATENT 3,658,525

The developing process which is revealed in US patent 3658525, (Bent and Mowrey inventors), discloses enough detailed information that a chemist skilled in photographic processing could use it to duplicate, basically, the method that Kodak used to process Kodachrome color film. A specific example is given on columns 9-11 of the patent, while other parts of the developing compositions are given earlier. Apparently the cyan and yellow developers use CD-4 in the patent, although a different developer--CD-3?--was used in practice.

The specific example in columns 9-11 states exactly the chemical used for the cyan coupler. This is:

CYAN COUPLER FOR KODACHROME FROM US PATENT 3658535

I-Hydroxy-N-(2-acetamidophenethyl)-2-naphthamide.


However, for the other two couplers the example only states the chemical properties which the yellow and the magenta couplers should have. It does not name the couplers exactly. The yellow coupler is of a class of chemicals called an alpha-pivalyl-acetanilide. In the list of sources for couplers given in the Kodachrome patent 3658525 (which appears in column 5), none of the sources listed shows a yellow coupler which is an alpha-pivalyl-acetanilide. However, in a patent about yellow dye couplers granted in 1966, US patent 3265505 (Weissberger and Kibler inventors) there are three dye couplers which are alpha-pivalyl-acetanilides, and which are also diffusible into an emulsion. These ought to be suitable for Kodachrome processing. They are called coupler 18, coupler 20 and coupler 25.


YELLOW COUPLERS FOR KODACHROME FROM US PATENT 3265505

Coupler 18, alpha-Pivalyl-3,5-dicarbomethoxyacetanilide;
Coupler 20, alpha-Pivaly1-alpha - (3 tetradecylcarbamylphenylthio)-3,5-di-carbomethoxyacetanilide.
Coupler 25, Alpha-pivalyl-alpha-( 3-octadecylcarbamyl phenylthio)-4-chlorosulfonylacetanilide


The Kodachrome example process in column 11 says the magenta coupler is a 5-pyrazolone coupler of U.S. Pat. No. 3,152,896. There are eight of these:


MAGENTA COUPLERS FOR KODACHROME FROM US PATENT 3152896

(1) 1 - (2,4,6 — trichlorophenyl) - 3 - (4 - methylsulfo~nylanilino) - 5 - pyrazolone
(2) 1- (2,4,K6-trichlorophenyl) —3- (4-cyanoanilino) —5-pyrazolone
(3) 1- ( 2,4,6-trichlorophenyl ) -3-( 3-cyanoanilino ) —5-pyrazolone
(4) 1- (Z,4,6-trichlorophenyl) —3-(2-chloro-5-cyanoanilino) —5-pyrazolone
(5) 1- (2,4,‘6-trichlorophenyl) —3- ( 3-nitroanilino) —5-pyrazolone
(6) l- (2,4,6-trichlorophenyl) —3- (2,4-dichloroanilino) —5 pyrazolone
(7) 1- (2,6-dichloro-4-nitrophenyl) —3- (2,4-dichloroanilino)—‘5-pyrazolone .
(8) 1- (2,6-dichloro-4-cyanophenyl ) —3- (2,4-dichloroani lino) —g 5-pyraz0l0ne

See column 4 of US Patent 3152896 for the structure for magenta coupler (1)

 

[piratelogy]

KODACHROME DYE COUPLERS FROM US PATENT 3,658,525

The developing process which is revealed in US patent 3658525, (Bent and Mowrey inventors), discloses enough detailed information that a chemist skilled in photographic processing could use it to duplicate, basically, the method that Kodak used to process Kodachrome color film. A specific example is given on columns 9-11 of the patent, while other parts of the developing compositions are given earlier. Apparently the cyan and yellow developers use CD-4 in the patent, although a different developer--CD-3?--was used in practice.

The specific example in columns 9-11 states exactly the chemical used for the cyan coupler. This is:

CYAN COUPLER FOR KODACHROME FROM US PATENT 3658535

I-Hydroxy-N-(2-acetamidophenethyl)-2-naphthamide.


However, for the other two couplers the example only states the chemical properties which the yellow and the magenta couplers should have. It does not name the couplers exactly. The yellow coupler is of a class of chemicals called an alpha-pivalyl-acetanilide. In the list of sources for couplers given in the Kodachrome patent 3658525 (which appears in column 5), none of the sources listed shows a yellow coupler which is an alpha-pivalyl-acetanilide. However, in a patent about yellow dye couplers granted in 1966, US patent 3265505 (Weissberger and Kibler inventors) there are three dye couplers which are alpha-pivalyl-acetanilides, and which are also diffusible into an emulsion. These ought to be suitable for Kodachrome processing. They are called coupler 18, coupler 20 and coupler 25.


YELLOW COUPLERS FOR KODACHROME FROM US PATENT 3265505

Coupler 18, alpha-Pivalyl-3,5-dicarbomethoxyacetanilide;
Coupler 20, alpha-Pivaly1-alpha - (3 tetradecylcarbamylphenylthio)-3,5-di-carbomethoxyacetanilide.
Coupler 25, Alpha-pivalyl-alpha-( 3-octadecylcarbamyl phenylthio)-4-chlorosulfonylacetanilide


The Kodachrome example process in column 11 says the magenta coupler is a 5-pyrazolone coupler of U.S. Pat. No. 3,152,896. There are eight of these:


MAGENTA COUPLERS FOR KODACHROME FROM US PATENT 3152896

(1) 1 - (2,4,6 — trichlorophenyl) - 3 - (4 - methylsulfo~nylanilino) - 5 - pyrazolone
(2) 1- (2,4,K6-trichlorophenyl) —3- (4-cyanoanilino) —5-pyrazolone
(3) 1- ( 2,4,6-trichlorophenyl ) -3-( 3-cyanoanilino ) —5-pyrazolone
(4) 1- (Z,4,6-trichlorophenyl) —3-(2-chloro-5-cyanoanilino) —5-pyrazolone
(5) 1- (2,4,‘6-trichlorophenyl) —3- ( 3-nitroanilino) —5-pyrazolone
(6) l- (2,4,6-trichlorophenyl) —3- (2,4-dichloroanilino) —5 pyrazolone
(7) 1- (2,6-dichloro-4-nitrophenyl) —3- (2,4-dichloroanilino)—‘5-pyrazolone .
(8) 1- (2,6-dichloro-4-cyanophenyl ) —3- (2,4-dichloroani lino) —g 5-pyraz0l0ne

Here is the structure for magenta coupler (1)

View attachment 171361

Hey, thanks for doing that legwork! I'll get with Sigma Aldrich and see if I can order any of those. It'd be nice to get closer to the correct couplers for sure.

 

[falotico]

Google has a service called Google Patents. Looking at the patents which I've cited can give you an idea about how these chemicals are synthesized. This might be helpful if they are not available commercially. By the way, I think your Kodachrome processing work is a valuable contribution to the field.

 

[piratelogy]

Google has a service called Google Patents. Looking at the patents which I've cited can give you an idea about how these chemicals are synthesized. This might be helpful if they are not available commercially. By the way, I think your Kodachrome processing work is a valuable contribution to the field.

Awesome, thats good to know. I'm hoping that I can get them commercially, as I'm pretty certain my chemistry skills are not up to synthesizing them myself. In any event what I've got going now is certainly within the realm of "works ok" and I'll be happy with that. But the closer I can get to the correct process the better, right?

 

[Photo Engineer]

Most Kodak yellow couplers are now based on Pivaloyl derivatives. This is for hue and stability. The magenta structure in the figure above is wrong. The cyan and magenta of K14 used CD3 and the yellow used CD6.

Try freepatentsonline.com for excellent search and display properties.

PE

 

[Craig]

Or for even better patent searching, go to the sources. Either the USPTO, or for a much easier to use search engine, the European Patent Office: https://worldwide.espacenet.com/?locale=en_EP

 

[piratelogy]

Most Kodak yellow couplers are now based on Pivaloyl derivatives. This is for hue and stability. The magenta structure in the figure above is wrong. The cyan and magenta of K14 used CD3 and the yellow used CD6.

Try freepatentsonline.com for excellent search and display properties.

PE

Awesome, so I'll ignore those magentas for now. I appreciate that link. A lot of the copies of the patents I'd found on Google were horrible OCRs that were very hard to decypher.

 

[falotico]

If you substitute couplers outside those referred to in US Patent 3,658,525 how can you be sure that they will diffuse through the emulsion?
(Sorry about posting an inaccurate structure of a magenta coupler; I misread two of the subscripts).

 

[piratelogy]

If you substitute couplers outside those referred to in US Patent 3,658,525 how can you be sure that they will diffuse through the emulsion?
(Sorry about posting an inaccurate structure of a magenta coupler; I misread two of the subscripts).

I can't be sure. The ones I've been using(Simpler couplers from an old book on color process) *DO*, as in I'm making decent color slides from them currently. But I only know they work by trial and error.

 

[Photo Engineer]

Awesome, so I'll ignore those magentas for now. I appreciate that link. A lot of the copies of the patents I'd found on Google were horrible OCRs that were very hard to decypher.

I did NOT say to ignore those magenta couplers. I just stated that the structure shown was wrong for one coupler. Almost all magenta couplers today are pyrazolones.

PE